SCH 4U Review - Organic Compounds PDF

**[[SCH 4U Review]]{.smallcaps}** **[[Chapter 1: Organic Compounds]]{.smallcaps}** **organic compound** -- a compound that contains carbon and usually hydrogen **catenation** -- the property of carbon to form a covalent bond with another carbon atom, forming long chains or rings **functional gro...

**[[SCH 4U Review]]{.smallcaps}** **[[Chapter 1: Organic Compounds]]{.smallcaps}** **organic compound** -- a compound that contains carbon and usually hydrogen **catenation** -- the property of carbon to form a covalent bond with another carbon atom, forming long chains or rings **functional group** -- a group of atoms in an organic molecule that impart particular physical and chemical characteristics to that molecule -- there are three main components: - - - **[Basic Naming]{.smallcaps}** **[Number]{.smallcaps}** **[Prefix for Naming]{.smallcaps}** **[Alkyl Group Name]{.smallcaps}** **[Functional Group]{.smallcaps}** **[Prefix for Naming]{.smallcaps}** -------------------------- ------------------------------------- ------------------------------------ ------------------------------------ ------------------------------------- 1 meth- methyl- \- F fluoro 2 eth- ethyl- \- Cl chloro 3 prop- propyl- \- Br bromo 4 but- butyl- \- I iodo 5 pent- pentyl- \- OH hydroxy 6 hex- hexyl- \- NO~2~ nitro 7 hept- heptyl- \- NH~2~ amino 8 oct- octyl- 9 non- nonyl- 10 dec- decyl- **[Isomers of Alkyl Groups]{.smallcaps}** +-----------------------------------+-----------------------------------+ | butyl (or *n*-butyl) | CH~3~ -- CH~2~ -- CH~2~ -- CH~2~ | +===================================+===================================+ | *iso*butyl (or *i*-butyl) | CH~3~ -- CH -- CH~3~ | | | | | | CH~2~ | +-----------------------------------+-----------------------------------+ | *s*-butyl (secondary butyl) | CH~3~ -- CH -- CH~2~ -- CH~3~ | +-----------------------------------+-----------------------------------+ | *t*-butyl (tertiary butyl) | CH~3~ | | | | | | CH~3~ -- C -- CH~3~ | +-----------------------------------+-----------------------------------+ **[Symbols]{.smallcaps}** R, R΄, R˝ alkyl group X halogen atom \(O) oxidizing agent (like KMnO~4~ or Cr~2~O~7~ ^2-^ in H~2~SO~4~) **[Priority for Naming (from highest to lowest)]{.smallcaps}** OH hydroxyl NH~2~ amino F, Cl, Br, I fluoro, chloro, bromo, iodo CH~2~CH~2~CH~3~ propyl CH~2~CH~3~ ethyl CH~3~ methyl [Alkanes]{.smallcaps} +-----------------------------------+-----------------------------------+ | **[Definition]{.smallcaps}** | a hydrocarbon with only single | | | bonds between carbon atoms; | | | general formula, C~n~H~2n+2~ | +===================================+===================================+ | **[Naming]{.smallcaps}** | prefix referring to number of | | | carbons in the longest continuous | | | chain + "-**ane**" | | | | | | - alkyl groups are named in | | | alphabetical order, numbered | | | from the end that will give | | | the lowest combination of | | | numbers | | | | | | - the presence of two or more | | | of the same alkyl groups | | | requires a "di" or "tri" | | | prefix before the alkyl group | | | name | | | | | | - cyclic hydrocarbons have the | | | carbon ring become the parent | | | chain, and the prefix | | | "**cyclo**" is used before | | | the parent name | +-----------------------------------+-----------------------------------+ | **[General Formula]{.smallcaps}** | -- C -- C -- | +-----------------------------------+-----------------------------------+ | **[Example(s)]{.smallcaps}** | propane CH~3~ -- CH~2~ -- CH~3~ | | | | | | cyclohexane CH~2~ | | | | | | CH~2~ CH~2~ | | | | | | \| \| | | | | | | CH~2~ CH~2~ | | | | | | CH~2~ | +-----------------------------------+-----------------------------------+ | **[Polarity]{.smallcaps}** | non-polar | +-----------------------------------+-----------------------------------+ | **[Forces]{.smallcaps}** | dispersion forces | +-----------------------------------+-----------------------------------+ | **[Boiling Point]{.smallcaps}** | - relatively low | | | | | | - increases with chain length | | | | | | - straight chains have higher | | | b.p.s than branched chains | +-----------------------------------+-----------------------------------+ | **[Solubility]{.smallcaps}** | immiscible in water and other | | | polar solvents | +-----------------------------------+-----------------------------------+ | **[Reactions]{.smallcaps}** | combustion | | | | | | C~3~H~8~ + **5** O~2~ **3** CO~2~ | | | + **4** H~2~O | +-----------------------------------+-----------------------------------+ | | substitution (halogenation) | | | | | | 1\) CH~4~ + Cl~2~ CH~3~Cl + HCl | | | | | | 2\) CH~3~Cl + Cl~2~ CH~2~Cl~2~ + | | | HCl | +-----------------------------------+-----------------------------------+ [Alkenes]{.smallcaps} +-----------------------------------+-----------------------------------+ | **[Definition]{.smallcaps}** | a hydrocarbon that contains at | | | least one carbon-carbon double | | | bond; general formula, C~n~H~2n~ | +===================================+===================================+ | **[Naming]{.smallcaps}** | prefix referring to number of | | | carbons in the longest continuous | | | chain *that contains the double | | | bond* + "-**ene**" | | | | | | - alkyl groups are named in | | | alphabetical order, numbered | | | from the end that is closest | | | to the double bond | +-----------------------------------+-----------------------------------+ | **[General Formula]{.smallcaps}** | \| \| | | | | | | -- C = C -- | +-----------------------------------+-----------------------------------+ | **[Example(s)]{.smallcaps}** | propene CH~2~ = CH -- CH~3~ | +-----------------------------------+-----------------------------------+ | **[Polarity]{.smallcaps}** | non-polar | +-----------------------------------+-----------------------------------+ | **[Forces]{.smallcaps}** | dispersion forces | +-----------------------------------+-----------------------------------+ | **[Boiling Point]{.smallcaps}** | relatively low | +-----------------------------------+-----------------------------------+ | **[Solubility]{.smallcaps}** | immiscible in water and other | | | polar solvents | +-----------------------------------+-----------------------------------+ | **[Reactions]{.smallcaps}** | halogenation (with Br~2~, Cl~2~, | | | etc.) | | | | | | ethene + bromine 1,2 -- | | | dibromoethane | | | | | | Br Br | | | | | | CH~2~ **=** CH~2~ + Br~2~ CH~2~ | | | -- CH~2~ | +-----------------------------------+-----------------------------------+ | | hydrogenation (with H~2~) | | | | | | ethyne + hydrogen ethane | | | | | | H H | | | | | | CH~2~ **=** CH~2~ + **2** H~2~ | | | CH~2~ -- CH~2~ | | | | | | H H | +-----------------------------------+-----------------------------------+ | | hydrohalogenation (with hydrogen | | | halides) | | | | | | propene + hydrogen bromine | | | 2-bromopropane | | | | | | H Br | | | | | | \| \| | | | | | | H -- C **=** CH -- CH~3~ + HBr H | | | -- C -- CH -- CH~3~ | | | | | | \| \| | | | | | | H H | +-----------------------------------+-----------------------------------+ | | hydration (with H~2~O) | | | | | | 1-butene + water 2-butanol | | | | | | CH~3~ -- CH~2~ -- CH **=** CH~2~ | | | + HOH CH~3~ -- CH~2~ -- CH -- | | | CH~2~ | | | | | | OH H | +-----------------------------------+-----------------------------------+ | **[Markovnikov's | "The rich get richer"... when a | | Rule]{.smallcaps}** | hydrogen halide or water is added | | | to an alkene or alkyne, the | | | hydrogen atom bonds to the carbon | | | atom within the double bond that | | | *already has more hydrogen | | | bonds*. | +-----------------------------------+-----------------------------------+ | **[Geometric | - a **cis isomer** has both | | Isomers]{.smallcaps}** | alkyl groups on the same side | | | of the molecular strucutre | | | | | | CH~3~ CH~3~ | | | | | | C = C *cis-2-butene* | | | | | | H H | | | | | | - a **trans isomer** has alkyl | | | groups on the opposite side | | | of the molecular strucutre | | | | | | CH~3~ H | | | | | | C = C *trans-2-butene* | | | | | | H CH~3~ | +-----------------------------------+-----------------------------------+ [Alkynes]{.smallcaps} +-----------------------------------+-----------------------------------+ | **[Definition]{.smallcaps}** | a hydrocarbon that contains at | | | least one carbon-carbon triple | | | bond; general formula, | | | C~n~H~2n-2~ | +===================================+===================================+ | **[Naming]{.smallcaps}** | prefix referring to number of | | | carbons in the longest continuous | | | chain *that contains the triple | | | bond* + "-**yne**" | | | | | | - alkyl groups are named in | | | alphabetical order, numbered | | | from the end that is closest | | | to the triple bond | +-----------------------------------+-----------------------------------+ | **[General Formula]{.smallcaps}** | -- C ≡ C -- | +-----------------------------------+-----------------------------------+ | **[Example(s)]{.smallcaps}** | propyne CH ≡ C -- CH~3~ | +-----------------------------------+-----------------------------------+ | **[Polarity]{.smallcaps}** | non-polar | +-----------------------------------+-----------------------------------+ | **[Forces]{.smallcaps}** | dispersion forces | +-----------------------------------+-----------------------------------+ | **[Boiling Point]{.smallcaps}** | relatively low | +-----------------------------------+-----------------------------------+ | **[Solubility]{.smallcaps}** | immiscible in water and other | | | polar solvents | +-----------------------------------+-----------------------------------+ | **[Reactions]{.smallcaps}** | *Same as Alkenes (resulting in | | | double bonds rather than single)* | +-----------------------------------+-----------------------------------+ [Aromatic Hydrocarbons]{.smallcaps} +-----------------------------------+-----------------------------------+ | **[Definition]{.smallcaps}** | a compound with a structure based | | | on benzene (a ring of six | | | carbons) | +===================================+===================================+ | **[Naming]{.smallcaps}** | consider the benzene ring to be | | | the parent molecule | | | | | | - alkyl groups are named to | | | give the lowest combination | | | of numbers, with no | | | particular starting carbon | | | (as it is a ring) | | | | | | - when it is easier to consider | | | the benzene ring as an alkyl | | | group, we use the name | | | "**phenyl**" to refer to it | +-----------------------------------+-----------------------------------+ | **[General Formula]{.smallcaps}** | | +-----------------------------------+-----------------------------------+ | **[Example(s)]{.smallcaps}** | methylbenzene | +-----------------------------------+-----------------------------------+ | **[Polarity]{.smallcaps}** | non-polar | +-----------------------------------+-----------------------------------+ | **[Forces]{.smallcaps}** | dispersion forces | +-----------------------------------+-----------------------------------+ | **[Boiling Point]{.smallcaps}** | relatively low | +-----------------------------------+-----------------------------------+ | **[Solubility]{.smallcaps}** | immiscible in water and other | | | polar solvents | +-----------------------------------+-----------------------------------+ | **[Reactions]{.smallcaps}** | *Same as Alkanes (performs | | | substitution reactions)* | +-----------------------------------+-----------------------------------+ [Organic Halides]{.smallcaps} +-----------------------------------+-----------------------------------+ | **[Definition]{.smallcaps}** | a compound of carbon and hydrogen | | | in which one or more hydrogen | | | atoms have been replaced by | | | halogen atoms | +===================================+===================================+ | **[Naming]{.smallcaps}** | halogen atoms are considered to | | | be attachments to the parent | | | chain and are numbered and named | | | with a prefix as such | +-----------------------------------+-----------------------------------+ | **[General Formula]{.smallcaps}** | R -- X | +-----------------------------------+-----------------------------------+ | **[Example(s)]{.smallcaps}** | H H | | | | | | \| \| | | | | | | 1,2-dichloroethane H -- C -- C -- | | | H | | | | | | \| \| | | | | | | Cl Cl | | | | | | Cl | | | | | | 1,2-dichlorobenzene | | | | | | Cl | +-----------------------------------+-----------------------------------+ | **[Polarity]{.smallcaps}** | polar (due to halogen atom) | +-----------------------------------+-----------------------------------+ | **[Forces]{.smallcaps}** | dispersion forces (increased | | | strength b/c of carbon-halogen | | | bonds) | +-----------------------------------+-----------------------------------+ | **[Boiling Point]{.smallcaps}** | higher than the corresponding | | | hydrocarbons | +-----------------------------------+-----------------------------------+ | **[Solubility]{.smallcaps}** | more soluble in polar solvents | +-----------------------------------+-----------------------------------+ | **[Reactions]{.smallcaps}** | addition | | | | | | ethylene + hydrogen idodie | | | 1-iodoethene | | | | | | H I | | | | | | \| \| | | | | | | H -- C ≡ C -- H + H -- I H -- C = | | | C -- H | +-----------------------------------+-----------------------------------+ | | substitution | | | | | | ethane + chlorine 1-chloroethane | | | + hydrogen chloride | | | | | | H Cl | | | | | | CH~3~ -- CH~3~ + Cl -- Cl H -- C | | | -- C -- H + H -- Cl | | | | | | H H | +-----------------------------------+-----------------------------------+ | | elimination | | | | | | 2-bromopropane + hydroxyl group | | | propene + bromine ion + water | | | | | | H Br H H H H | | | | | | \| \| \| | | | | | | H -- C -- C -- C -- H + OH^-^ H | | | -- C -- C = C -- H + Br^-^ + | | | H~2~O | | | | | | H H H H | +-----------------------------------+-----------------------------------+ [Alcohols]{.smallcaps} +-----------------------------------+-----------------------------------+ | **[Definition]{.smallcaps}** | an organic compound characterized | | | by the presence of a hydroxyl | | | functional group (OH^-^) | +===================================+===================================+ | **[Naming]{.smallcaps}** | - the "e" ending of the parent | | | hydrocarbon is changed to | | | "**ol**" to indicate the | | | presence of the OH^-^ group | | | | | | - the chain is numbered to give | | | the OH^-^ group the smallest | | | possible number | | | | | | - when there is more than one | | | OH^-^ group, the endings | | | "diol" and "triol" are used, | | | and each is indicated with a | | | numerical prefix, however the | | | "e" ending remain then (e.g., | | | 1,3-propanediol) | +-----------------------------------+-----------------------------------+ | **[General Formula]{.smallcaps}** | R -- OH | +-----------------------------------+-----------------------------------+ | **[Example(s)]{.smallcaps}** | propanol CH~3~ -- CH~2~ -- CH~2~ | | | -- OH | | | | | | phenol | +-----------------------------------+-----------------------------------+ | **[Polarity]{.smallcaps}** | polar (due to hydroxyl group) | +-----------------------------------+-----------------------------------+ | **[Forces]{.smallcaps}** | hydrogen bonding and dispersion | | | forces | +-----------------------------------+-----------------------------------+ | **[Boiling Point]{.smallcaps}** | high (due to capacity for | | | hydrogen bonding) | +-----------------------------------+-----------------------------------+ | **[Solubility]{.smallcaps}** | very soluble in polar solvents | | | and nonpolar solvents (due to | | | OH^-^ group) | +-----------------------------------+-----------------------------------+ | | hydration (preparation) | | | | | | 1-butene + water 2-butanol | | | | | | CH~3~ -- CH~2~ -- CH **=** CH~2~ | | | + HOH CH~3~ -- CH~2~ -- CH -- | | | CH~2~ | | | | | | OH H | +-----------------------------------+-----------------------------------+ | | dehydration (elimination) | | | | | | propanol propene + water | | | | | | CH~3~ -- CH -- CH~2~ CH~3~ -- CH | | | = CH~2~ + HOH | | | | | | OH H | +-----------------------------------+-----------------------------------+ | **[1°, 2°, and 3° | **Primary** Alcohol (1°) CH~3~ -- | | Alcohols]{.smallcaps}** | CH~2~ -- OH | | | | | | 1 other carbon group attached to | | | carbon with OH | | | | | | OH | | | | | | **Secondary** Alcohol (2°) CH~3~ | | | -- CH -- CH~3~ | | | | | | 2 other carbon groups attached to | | | carbon with OH | | | | | | OH | | | | | | **Tertiary** Alcohol (3°) CH~3~ | | | -- C -- CH~3~ | | | | | | 3 other carbon groups attached to | | | carbon with OH | | | | | | CH~3~ | +-----------------------------------+-----------------------------------+ [Ethers]{.smallcaps} +-----------------------------------+-----------------------------------+ | **[Definition]{.smallcaps}** | an organic compound with two | | | alkyl groups (the same or | | | different) attached to an oxygen | | | atom | +===================================+===================================+ | **[Naming]{.smallcaps}** | - the longer of the two alkyl | | | groups is considered the | | | parent chain | | | | | | - the other alkyl group with | | | the oxygen is considered to | | | be the substituent group | | | (with prefix of carbons and | | | "**oxy**") | | | | | | - numbering of C atoms starts | | | at the O | | | | | | propane ethoxy | | | | | | CH~3~CH~2~CH~2~ -- O -- | | | CH~2~CH~3~ | | | | | | **^3\ 2\ 1\ 1\ 2^** | | | | | | *ethoxypropane* | +-----------------------------------+-----------------------------------+ | **[General Formula]{.smallcaps}** | R -- O -- R΄ | +-----------------------------------+-----------------------------------+ | **[Example(s)]{.smallcaps}** | methoxyethane CH~3~ -- O -- CH~2~ | | | -- CH~3~ | +-----------------------------------+-----------------------------------+ | **[Polarity]{.smallcaps}** | polar (due to the V-shape and C - | | | O bonds) | +-----------------------------------+-----------------------------------+ | **[Forces]{.smallcaps}** | dispersion forces | +-----------------------------------+-----------------------------------+ | **[Boiling Point]{.smallcaps}** | medium (higher than hydrocarbons, | | | lower than alcohols of similar | | | length) | +-----------------------------------+-----------------------------------+ | **[Solubility]{.smallcaps}** | soluble in polar solvents and | | | nonpolar solvents | +-----------------------------------+-----------------------------------+ | | condensation (preparation) \* | | | addition of two alcohols (same or | | | different) \* | | | | | | methanol + methanol | | | methoxymethane + water | | | | | | CH~3~ -- OH + CH~3~ -- OH CH~3~ | | | -- O -- CH~3~ + HOH | +-----------------------------------+-----------------------------------+ [Aldehydes]{.smallcaps} +-----------------------------------+-----------------------------------+ | **[Definition]{.smallcaps}** | an organic compound that contains | | | the carbonyl group (--C=O) on the | | | end carbon of a chain | +===================================+===================================+ | **[Naming]{.smallcaps}** | the "e" ending of the parent | | | hydrocarbon is changed to | | | "**al**" to indicate the presence | | | of the R-C=O | +-----------------------------------+-----------------------------------+ | **[General Formula]{.smallcaps}** | O | | | | | | \|\| | | | | | | R\[H\] -- C -- H | +-----------------------------------+-----------------------------------+ | **[Example(s)]{.smallcaps}** | O | | | | | | \|\| | | | | | | propanal CH~3~ -- CH~2~ -- C -- H | +-----------------------------------+-----------------------------------+ | **[Polarity]{.smallcaps}** | polar (due to carbonyl group) | +-----------------------------------+-----------------------------------+ | **[Forces]{.smallcaps}** | dispersion forces | +-----------------------------------+-----------------------------------+ | **[Boiling Point]{.smallcaps}** | medium (higher than ethers, lower | | | than alcohols of similar length) | +-----------------------------------+-----------------------------------+ | **[Solubility]{.smallcaps}** | similar solubility to alcohols | +-----------------------------------+-----------------------------------+ | **[Reactions]{.smallcaps}** | oxidation (preparation) | | | | | | **1° alcohol + mild oxidizing | | | agent aldehyde + water** | | | | | | ethanol + (O) ethanal + water | | | | | | OH O | | | | | | \| \|\| | | | | | | CH~3~ -- C -- H + (O) CH~3~ -- C | | | -- H + HOH | | | | | | \| | | | | | | H | +-----------------------------------+-----------------------------------+ | | reduction (hydrogenation) | | | | | | **aldehyde + hydrogen 1° | | | alcohol** | | | | | | proponal + hydrogen 1-propanol | | | | | | O OH | | | | | | CH~3~ -- CH~2~ -- C -- H + H~2~ | | | CH~3~ -- CH~2~ -- C -- H | +-----------------------------------+-----------------------------------+ [Ketones]{.smallcaps} +-----------------------------------+-----------------------------------+ | **[Definition]{.smallcaps}** | an organic compound that contains | | | the carbonyl group (--C=O) on a | | | carbon other than those on the | | | end of a carbon chain (in the | | | middle) | +===================================+===================================+ | **[Naming]{.smallcaps}** | the "e" ending of the parent | | | hydrocarbon is changed to | | | "**one**" | +-----------------------------------+-----------------------------------+ | **[General Formula]{.smallcaps}** | O | | | | | | \|\| | | | | | | R -- C -- R΄ | +-----------------------------------+-----------------------------------+ | **[Example(s)]{.smallcaps}** | O | | | | | | \|\| | | | | | | propanone (acetone) CH~3~ -- C -- | | | CH~3~ | +-----------------------------------+-----------------------------------+ | **[Polarity]{.smallcaps}** | polar (due to carbonyl group) | +-----------------------------------+-----------------------------------+ | **[Forces]{.smallcaps}** | dispersion forces | +-----------------------------------+-----------------------------------+ | **[Boiling Point]{.smallcaps}** | medium (higher than ethers, lower | | | than alcohols of similar length) | +-----------------------------------+-----------------------------------+ | **[Solubility]{.smallcaps}** | similar solubility to alcohols | +-----------------------------------+-----------------------------------+ | **[Reactions]{.smallcaps}** | oxidation (preparation) | | | | | | **2° alcohol + oxidizing agent | | | ketone + water** | | | | | | 2-propanol + (O) propanone + | | | water | | | | | | OH O | | | | | | \|\| | | | | | | CH~3~ -- C -- CH~3~ + (O) CH~3~ | | | -- C -- CH~3~ + HOH | | | | | | H | +-----------------------------------+-----------------------------------+ | | reduction (hydrogenation) | | | | | | **ketone + hydrogen 2° alcohol** | | | | | | butanone + hydrogen 2-butanal | | | | | | O OH | | | | | | CH~3~ -- CH~2~ -- C -- CH~3~ + | | | H~2~ CH~3~ -- CH~2~ -- C -- CH~3~ | +-----------------------------------+-----------------------------------+ | | **[Note]{.smallcaps}**: Tertiary | | | alcohols do not undergo oxidation | | | reactions; no H atom is available | | | on the central C atom. | +-----------------------------------+-----------------------------------+ [Carboxylic Acids]{.smallcaps} +-----------------------------------+-----------------------------------+ | **[Definition]{.smallcaps}** | one of a family of organic | | | compounds that is characterized | | | by the presence of a carboxyl | | | group: | | | | | | -- C | | | | | | O -- H | +===================================+===================================+ | **[Naming]{.smallcaps}** | - the "e" ending of the parent | | | alkane is changed to "**oic | | | acid**" | | | | | | | | | | | | - numbering starts with the C | | | of the carboxyl group | +-----------------------------------+-----------------------------------+ | **[General Formula]{.smallcaps}** | O | | | | | | \|\| | | | | | | R\[H\] -- C -- OH | +-----------------------------------+-----------------------------------+ | **[Example(s)]{.smallcaps}** | CH~2~CH~3~ | | | | | | 4-ethyl-3-methylhexanoic acid | | | CH~3~ -- CH~2~ -- CH -- CH -- | | | CH~2~ -- COOH | | | | | | CH~3~ | +-----------------------------------+-----------------------------------+ | **[Polarity]{.smallcaps}** | polar (due to carboxyl group) | +-----------------------------------+-----------------------------------+ | **[Forces]{.smallcaps}** | dispersion forces and hydrogen | | | bonding | +-----------------------------------+-----------------------------------+ | **[Boiling Point]{.smallcaps}** | very high (higher than | | | hydrocarbons of similar length | | | due to --CO and --OH groups) | +-----------------------------------+-----------------------------------+ | **[Solubility]{.smallcaps}** | similar solubility to alcohols | +-----------------------------------+-----------------------------------+ | **[Reactions]{.smallcaps}** | dissolution in water (proof of | | | acidity) | | | | | | ethanoic acid + water carboxylate | | | ion + hydronium ion | | | | | | CH~3~COOH + H~2~O CH~3~COO^-^ + | | | H~3~O^+^ | | | | | | O -- | | | | | | CH~3~ -- C \* shares the double | | | bond | | | | | | O | +-----------------------------------+-----------------------------------+ | | oxidation (with weak oxidizer) | | | | | | **1) 1° alcohol + weak oxidizing | | | agent aldehyde + water** | | | | | | **2) aldehyde + weak oxidizing | | | agent carboxylic acid + water** | | | | | | O | | | | | | **1)** CH~3~ -- CH~2~ -- OH + | | | Cr~2~O~7~^2-^ + H^+^ CH~3~ -- C | | | -- H + H~2~O + Cr^3+^ | | | | | | O | | | | | | **2)** CH~3~ -- C -- H + | | | Cr~2~O~7~^2-^ + **2** H^+^ **3** | | | CH~3~ -- COOH + **4** H~2~O | +-----------------------------------+-----------------------------------+ | | oxidation (with strong oxidizer) | | | | | | **1° alcohol + strong oxidizing | | | agent carboxylic acid + water** | | | | | | ethanol + oxidizing agent + | | | hydrogen ethanoic acid + water + | | | manganese dioxide | | | | | | O | | | | | | **3** CH~3~ -- CH~2~ -- OH + | | | **4** MnO~4~^-^ + **4** H^+^ | | | **3** CH~3~ -- C -- OH + **5** | | | H~2~O + **4** MnO~2~ | +-----------------------------------+-----------------------------------+ | **[Note:]{.smallcaps}** | Ketones are not readily | | | oxidizing, as in the oxidation of | | | aldehydes. | +-----------------------------------+-----------------------------------+ [Esters]{.smallcaps} +-----------------------------------+-----------------------------------+ | **[Definition]{.smallcaps}** | an organic compound characterized | | | by the presence of a carbonyl | | | group bonded to an oxygen atom | +===================================+===================================+ | **[Naming]{.smallcaps}** | - the group that is attached to | | | the double-bonded O becomes | | | the parent chain with the "e" | | | ending changed to "**oate**" | | | | | | | | | | | | - the other group is named as a | | | substituent group | +-----------------------------------+-----------------------------------+ | **[General Formula]{.smallcaps}** | O | | | | | | \|\| | | | | | | R\[H\] -- C -- O -- R΄ | +-----------------------------------+-----------------------------------+ | **[Example(s)]{.smallcaps}** | 2-methylbutyl propanoate O CH~3~ | | | | | | CH~3~ -- CH~2~ -- C -- O -- CH~2~ | | | -- CH -- CH~2~ -- CH~3~ | +-----------------------------------+-----------------------------------+ | **[Polarity]{.smallcaps}** | less polar than carboxylic acids | | | (loss of OH^-^ group) | +-----------------------------------+-----------------------------------+ | **[Forces]{.smallcaps}** | dispersion forces | +-----------------------------------+-----------------------------------+ | **[Boiling Point]{.smallcaps}** | medium (lower than carboxylic | | | acids, higher than aldehydes / | | | ketones of similar length due to | | | extra O) | +-----------------------------------+-----------------------------------+ | **[Solubility]{.smallcaps}** | less soluble than acids | +-----------------------------------+-----------------------------------+ | **[Reactions]{.smallcaps}** | condensation (formation) | | | | | | **carboxylic acid + alcohol ester | | | + water** | | | | | | ethanoic acid + methanol methyl | | | ethanoate + water | | | | | | O O | | | | | | \|\| \|\| | | | | | | CH~3~ -- C -- OH + CH~3~ -- OH | | | CH~3~ -- C -- O -- CH~3~ + H~2~O | +-----------------------------------+-----------------------------------+ | | hydrolysis (saponification) | | | | | | **ester + NaOH sodium salt of | | | acid + alcohol** | | | | | | O O | | | | | | R -- C -- O -- R΄ + Na^+^ + OH^-^ | | | R -- C -- O^-^ + Na^+^ + R΄ -- OH | +-----------------------------------+-----------------------------------+ | **[Note:]{.smallcaps}** | Esters generally have nice odours | | | and are used to create artificial | | | flavours. | +-----------------------------------+-----------------------------------+ [Amines]{.smallcaps} +-----------------------------------+-----------------------------------+ | **[Definition]{.smallcaps}** | an ammonia molecule in which one | | | or more H atoms are substituted | | | by alkyl or aromatic groups | +===================================+===================================+ | **[Naming]{.smallcaps}** | 1. nitrogen group is named as a | | | substituent group using | | | "**amino-**" | | | | | | 2. alkyl group is named as a | | | substituent group from | | | "-**amine**" | +-----------------------------------+-----------------------------------+ | **[General Formula]{.smallcaps}** | R΄ \[H\] | | | | | | \| | | | | | | R -- N -- R΄΄ \[H\] | +-----------------------------------+-----------------------------------+ | **[Example(s)]{.smallcaps}** | 1\) 1-aminopropane NH~2~ | | | | | | 2\) propylamine | | | | | | CH~2~ -- CH~2~ -- CH~3~ | +-----------------------------------+-----------------------------------+ | | N-ethyl-N-methyl-1-aminobutane | | | | | | CH~2~CH~3~ | | | | | | \| | | | | | | CH~3~ -- N -- CH~2~ -- CH~2~ -- | | | CH~2~ -- CH~3~ | +-----------------------------------+-----------------------------------+ | **[Polarity]{.smallcaps}** | polar (not as polar as alcohols, | | | because N is less polar than O) | +-----------------------------------+-----------------------------------+ | **[Forces]{.smallcaps}** | dispersion forces and N-H bonds | +-----------------------------------+-----------------------------------+ | **[Boiling Point]{.smallcaps}** | medium (lower than alcohols of | | | similar length, higher than | | | hydrocarbons) | +-----------------------------------+-----------------------------------+ | **[Solubility]{.smallcaps}** | soluble in water | +-----------------------------------+-----------------------------------+ | **[Reactions]{.smallcaps}** | formation | | | | | | **alkyl halide + ammonia amine + | | | ammonium halide** | | | | | | iodoethane + ammonia aminoethane | | | + ammonium iodide | | | | | | CH~3~ -- CH~2~ -- I + **2** NH~3~ | | | CH~3~ -- CH~2~ -- NH~2~ + NH~4~I | +-----------------------------------+-----------------------------------+ | **[1°, 2°, and 3° | **Primary** Amine (1°) CH~3~ -- N | | Amines]{.smallcaps}** | -- H | | | | | | 1 alkyl group attached to N \| | | | | | | H *methylamine* | +-----------------------------------+-----------------------------------+ | | **Secondary** Amine (2°) CH~3~ -- | | | N -- CH~3~ | | | | | | 2 alkyl groups attached to N \| | | | | | | H *dimethylamine* | +-----------------------------------+-----------------------------------+ | | **Tertiary** Amine (3°) CH~3~ -- | | | N -- CH~3~ | | | | | | 3 alkyl groups attached to N \| | | | | | | CH~3~ *trimethylamine* | +-----------------------------------+-----------------------------------+ [Amides]{.smallcaps} +-----------------------------------+-----------------------------------+ | **[Definition]{.smallcaps}** | an organic compound characterized | | | by the presence of a carbonyl | | | functional group (C=O) bonded to | | | a nitrogen atom | +===================================+===================================+ | **[Naming]{.smallcaps}** | alkyl group attached to | | | double-bonded O is considered to | | | be the substituent group, | | | attached to the parent | | | "-**amide**" | +-----------------------------------+-----------------------------------+ | **[General Formula]{.smallcaps}** | O R΄΄ \[H\] | | | | | | \|\| \| | | | | | | R\[H\] -- C -- N -- R΄ \[H\] | +-----------------------------------+-----------------------------------+ | **[Example(s)]{.smallcaps}** | O | | | | | | \|\| | | | | | | propanamide CH~3~ -- CH~2~ -- C | | | -- NH~2~ | +-----------------------------------+-----------------------------------+ | **[Polarity]{.smallcaps}** | slightly more polar than amine of | | | similar length (extra O) | +-----------------------------------+-----------------------------------+ | **[Forces]{.smallcaps}** | dispersion forces and N-H bonds | +-----------------------------------+-----------------------------------+ | **[Boiling Point]{.smallcaps}** | *same as amines* | +-----------------------------------+-----------------------------------+ | **[Solubility]{.smallcaps}** | soluble in water | +-----------------------------------+-----------------------------------+ | **[Reactions]{.smallcaps}** | formation | | | | | | **carboxylic acid + amine amide + | | | water** | | | | | | ethanoic acid + ammonia | | | ethanamide + water | | | | | | O H O | | | | | | \|\| \| \|\| | | | | | | CH~3~ -- C -- OH + H -- N -- H | | | CH~3~ -- C -- NH~2~ + HOH | +-----------------------------------+-----------------------------------+ **[Example of a Stepped Synthesis Reaction]{.smallcaps}** *Write a series of equations for a method of synthesis for N-ethylethanamide from an alkane and ammonia.* 1\. ethane + chlorine chloroethane + hydrogen chloride CH~3~ -- CH~3~ + Cl -- Cl CH~3~ -- CH~2~ + H -- Cl \| Cl 2\. chloroethane + water ethanol + hydrogen chloride CH~3~ -- CH~2~ HOH CH~3~ -- CH~2~ + H -- Cl \| \| Cl OH 3\. ethanol + strong oxidizer ethanoic acid + water + manganese dioxide CH~3~ -- CH~2~ + MnO~4~^-^ CH~3~ -- C -- OH + HOH + MnO~2~ \| \|\| OH O 4\. chloroethane + ammonia aminoethane + ammonium chlorine CH~3~ -- CH~2~ + **2** H -- N -- H CH~3~ -- CH~2~ -- NH~2~ + NH~4~Cl \| \| Cl H 5\. ethanoic acid + aminoethane N-ethylethanamide + water O H \|\| \| CH~3~ -- C -- OH + CH~3~ -- CH~2~ -- NH~2~ CH~3~ -- C -- N -- CH~2~ -- CH~3~ + HOH \|\| O **[Common Names]{.smallcaps}** **[Common Name]{.smallcaps}** **[IUPAC Name]{.smallcaps}** **[Common Name]{.smallcaps}** **[IUPAC Name]{.smallcaps}** ------------------------------- ------------------------------ -- ------------------------------- ------------------------------ ethylene ethene formic acid carboxyl group (COOH) propylene propene acetic acid ethanoic acid acetylene ethyne toluene / phenyl methane methyl benzene formaldehyde methanal acetate ethanoate acetaldehyde ethanal acetamide ethanamide acetone propanone **[Flow Chart of Organic Reactions]{.smallcaps}** **[[Chapter 2: Polymers]]{.smallcaps}** **polymer** -- a molecule of large molar mass that consists of many repeating subunits called monomers; two types: addition and condensation **monomer** -- a molecule or compound usually containing carbon and of relatively low molecular weight and simple structure which is capable of conversion to polymers by combination with itself or other similar molecules or compounds **dimer** -- a molecule made up of two monomers **[[Addition Polymers]]{.smallcaps}** **addition polymer** -- a polymer formed when monomer units are linked through addition reactions; all atoms present in the monomer are retained in the polymer alkene + alkene polymer \| \| \| \| \| \| \| \| \| \| C = C + C = C -- C -- C -- C -- C -- ***or*** -- C -- C -- \| \| \| \| \| \| \| \| \| \| ~n~ - less reactive than their monomers, because the *unsaturated* alkene monomers have been transformed into *saturated* carbon skeletons of alkanes - forces of attraction are largely van der Waals attractions, which are individually weak, allowing the polymer chains to slide along each other, rendering them flexible and stretchable **[[Condensation Polymers]]{.smallcaps}** **condensation polymer** -- a polymer formed when monomer units are linked through condensation reactions; a small molecule is formed as a byproduct **polyester** -- a polymer formed by condensation reactions resulting in ester linkages between monomers dialcohol + dicarboxylic acid polyester (dimer) + water O O O O \|\| \|\| \|\| \|\| HO -- CH~2~ -- CH~2~ -- OH + C -- C -- O -- CH~2~ CH~2~ -- O -- C -- C -- + 2 H~2~O \| \| ~n~ HO OH **polyamide** -- a polymer formed by condensation reactions resulting in amide linkages between monomers; also known as a **nylon** diamine + dicarboxylic acid polyamide (dimer) + water H H O O H H O O \| \| \|\| \|\| \| \| \|\| \|\| N -- CH~2~ -- N + C -- C -- N -- CH~2~ -- N -- C -- C -- + 2 H~2~O \| \| \| \| ~n~ H H HO OH **[[Compounds of Life]]{.smallcaps}** **protein** -- a large complex molecule made up of one or more chains of *amino acids* (an amino group and carboxyl group attached to the same carbon atom) **carbohydrate** -- a compound of carbon, hydrogen, and oxygen, with a general formula C~x~(H~2~O)~y~ **fat** -- known chemically as a *triglyceride* (an ester of three fatty acids which are long-chain carboxylic acids and one glycerol molecule) \| H **nucleic acid** -- hereditary information stored in all living cells from which the information can be transferred; the chief types being DNA and RNA **[[Chapter 3: Atomic Theory]]{.smallcaps}** **[[The Bohr Atomic Theory]]{.smallcaps}** - electrons travel in the atom in circular orbits with quantized energy -- energy is restricted to only certain discrete quantities - there is a maximum number of electrons allowed in each orbit - electrons "jump" to a higher level when a *photon* (a quantum of light energy) is absorbed, resulting in absorption spectrum (series of dark lines) - electrons "drop" to a lower level when a photon is emitted, resulting in bright-line spectrum (series of bright lines) **[[Orbits vs. Orbitals]]{.smallcaps}** **orbit** -- 2-D path; fixed distance from nucleus; circular or elliptical path; 2n^2^ electrons per orbit **orbital** -- 3-D region in space; variable distance from nucleus; no path and varied shape of region; 2 electrons per orbital; predicted by Schrodinger's equation **[[Quantum Numbers to Describe Orbitals ]]{.smallcaps}** *n* -- principal quantum number or energy level *l* -- secondary quantum number or subshell (*s*, *p*, *d*, or *f*) *m~1~* -- magnetic quantum number (direction of the electron orbit) *m~2~* -- spin quantum number (can only be +½ or --½ to describe spin of electron) +-------------+-------------+-------------+-------------+-------------+ | **[Value | **[Sublevel | **[Number | **[Max. | **[Present | | of]{.smallc | Symbol]{.sm | of | Number of | at | | aps} | allcaps}** | Orbitals]{. | Electrons]{ | ]{.smallcap | | *l*** | | smallcaps}* |.smallcaps} | s}** | | | | * | ** | | | | | | | ***n* =** | +=============+=============+=============+=============+=============+ | 0 | ***s*** | 1 | 2 | 1-7 | +-------------+-------------+-------------+-------------+-------------+ | 1 | ***p*** | 3 | 6 | 2-7 | +-------------+-------------+-------------+-------------+-------------+ | 2 | ***d*** | 5 | 10 | 3-7 | +-------------+-------------+-------------+-------------+-------------+ | 3 | ***f*** | 7 | 14 | 4-7 | +-------------+-------------+-------------+-------------+-------------+ **[[Creating Energy-Level Diagrams]]{.smallcaps}** **energy-level diagram** -- interpretation of which orbital energy levels are occupied by electrons for a particular atom or ion; also called an orbital diagram e.g., ~9~F 2p 2s 1s **[Rules for Energy-Level Diagrams]{.smallcaps}** - Start adding electrons to the lowest energy level (1*s*) and build up from the bottom until the limit on the number of electrons for the particle is reached -- **the aufbau principle** - To obtain the correct order of orbitals for any atom, start at the hydrogen and move from left to right across the periodic table, filling the orbitals; see below:  - For anions, add extra electrons to the number for the atom. For cations, do the neutral atom first, and then subtract the required number of electrons from the orbitals with the highest principle quantum number, *n* (i.e., you would remove the electrons from 4*s*, rather than 3*d*.) - Each orbital will hold a maximum of two electrons that spin in opposite directions -- **the Pauli exclusion principle** - Electrons must be distributed among orbitals of equal energy so that as many electrons remain unpaired as possible -- **Hund's rule** - Half-filled and filled subshells are more stable than unfilled subshells as the overall energy state of the atom is lower after the electron is promoted to a lower energy level: **Predicted** **Actual** Cr: \[Ar\] Cr: \[Ar\] Cu: \[Ar\] Cu: \[Ar\] 4*s* 3*d* 4*s* 3*d* **[[Electron Configuration]]{.smallcaps}** **electron configuration** -- a method for communicating the location and number of electrons in electron energy levels e.g., O: 1s^2^ 2s^2^ 2p^4^ 3p^5^ S^2-^: 1s^2^ 2s^2^ 2p^6^ 3s^2^ 3p^6^ **shorthand electron configuration** -- when the electron configuration is written with the preceding noble gas placed before the subshell information (e.g., Cl: 1s^2^ 2s^2^ 2p^6^ 3s^2^ 3p^5^ becomes Cl: \[Ne\] 3s^2^ 3p^5^) **isoelectronic** -- when two atoms/ions have the same electron configuration (e.g., Ne, F^-^, Na^+^) **ferromagnetism** -- exhibited by the metals iron, cobalt, nickel and a number of alloys that become magnetized in a magnetic field and retain their magnetism when the field is removed **paramagnetism** -- exhibited by materials like aluminum or platinum that become magnetized in a magnetic field but it disappears when the field is removed (caused by unpaired electrons) **[[Quantum Mechanic Theory]]{.smallcaps}** **quantum mechanics** -- the current theory of atomic structure based on wave properties of electrons; also known as wave mechanics **Heisenberg uncertainty princple** -- it is impossible to simultaneously know exact position and speed of an electron **electron probablity density** -- a mathematical or graphical representation of the chance of finding an electron in a given space; see below for example of a 2s orbital:  **[[Chapter 4: Chemical Bonding]]{.smallcaps}** **chemical bond** -- formed as the result of the simultaneous attraction of two or more nuclei **[[Types of Bonds]]{.smallcaps}** 1\. **Ionic Bonding** -- when one atom has low ionization energy and low En, while the other has high ionization energy and high En (i.e., metal and nonmetal) -- Δ En \> 1.7 -- the electrostatic attraction between positive and negative ions 2\. **Covalent Bonding** -- when both atoms have high ionization energy and high En (i.e., two nonmetals) -- Δ En ≤ 1.7 -- the sharing of valence electrons between atomic nuclei 3\. **Metallic Bonding** -- when both atoms have low ionization energy and low En (i.e., two metals) **[[Lewis Theory of Bonding]]{.smallcaps}** - Atoms and ions are stable if they have a noble gas-like electron structure (i.e., a stable octet of electrons). - Electrons are most stable when they are paired. - Atoms form chemical bonds to achieve a stable octet of electrons. - A stable octet may be achieved by an exchange of electrons between metal and nonmetal atoms. - A stable octet may be achieved by the sharing of electrons between nonmetal atoms, resulting in a covalent bond. **[[Lewis Structures]]{.smallcaps}** **Lewis structure** -- a symbolic depiction of the distribution of valence electrons in a molecule 1. Arrange atoms symmetrically around the central atom (usually listed first in the formula, not usually oxygen and never hydrogen). 2. Count the number of valence electrons of all atoms. For polyatomic ions, add electrons corresponding to the negative charge, and subtract electrons corresponding to the positive charge on the ion. 3. Determine the number of valence electrons all the atoms "want", and subtract the number of valence electrons it has (result from step 2). Divide this number by 2 to determine the number of bonds the molecule will have. 4. Place a bonding pair of electrons between the central atom and each of the surrounding atoms. 5. Complete the octets of the surrounding atoms using lone pairs of electrons. Remember hydrogen (2 e^-^), beryllium (4 e^-^), and boron (6 e^-^) are the exceptions. Any remaining electrons go on the central atom. 6. If the central atom does not have an octet, move lone pairs from the surrounding atoms to form double or triple bonds until the central atom has a complete octet. Confirm the number of bonds is correct by comparing it to the result in step 3. 7. Draw the Lewis structure and enclose polyatomic ions within square brackets showing the ion chare. e.g., SO~3~ **S** **O~3~** ------------ ------- ---------- -------- ----------- has 6 3 (6) 6 + 18 = 24 e^-^ wants 8 3 (8) 8 + 24 = 32 e^-^ difference = 8 e^-^ = 4 bonds **[[Valence Bond Theory]]{.smallcaps}** - Covalent bonds form when atomic or hybrid orbitals with one electron overlap to share e^-^. - Bonding occurs with the highest energy (valence shell) electrons. - Normally, the *s* orbitals (sphere shape) and *p* orbitals (dumb-bell shape) overlap with each other to form bonds between atoms. - *sp^3^*, *sp^2^*, and *sp* hybrid orbitals are formed from one *s* orbital and three, two, and one *p* orbital, respectively, with orientations of tetrahedral (109.5°), trigonal planar (120°), and linear (180°), respectively. - End-to-end overlap of orbitals or single covalent bonds is called a sigma (σ) bond. - Side-by-side overlap of unhybridized *p* orbitals is called a pi (Π) bond (weaker than σ bond). - Double bonds have one pi bond, while triple bonds have two pi bonds. **[[VSEPR Theory]]{.smallcaps}** **V**alence-**S**hell **E**lectron-**P**air **R**epulsion **Theory** -- pairs of electrons in the valence shell of an atom stay as far apart as possible to minimize repulsion of their negative charges 1. Draw the Lewis structure for the molecule, including the e^-^ pairs around the central atom. 2. Count the total number of bonding pairs and lone pairs of electrons around the central atom. 3. Use the table below to predict the shape of the molecule. +---------+---------+---------+---------+---------+---------+---------+ | [\# | [Orient | [Number | [Bond | [Shape] | [Exampl | [Molecu | | of]{.sm | ation | of | Angles] | {.small | e]{.sma | lar | | allcaps | of | Bonding | {.small | caps} | llcaps} | Geometr | | } | Electro | and | caps} | | | y]{.sma | | e^-^ | n | Lone | | | | llcaps} | | [Pairs | Pairs]{ | Pairs]{ | | | | | | Around |.smallc |.smallc | | | | | | Central | aps} | aps} | | | | | | Atom]{. | | | | | | | | smallca | | | | | | | | ps} | | | | | | | +=========+=========+=========+=========+=========+=========+=========+ | 2 | linear | 2 BP, 0 | 180° | linear | BeF~2~ | X -- A | | | | LP | | | | -- X | +---------+---------+---------+---------+---------+---------+---------+ | 3 | triangu | 3 BP, 0 | 120° | trigona | BF~3~ | X | | | lar | LP | | l | | | | | planar | | | planar | | \| | | | | | | | | | | | | | | | | A | | | | | | | | | | | | | | | | X X | +---------+---------+---------+---------+---------+---------+---------+ | 4 | tetrahe | 4 BP, 0 | 109.5° | tetrahe | CH~4~ | X | | | dral | LP | | dral | | | | | | | | | | \| | | | | | | | | | | | | | | | | A | | | | | | | | | | | | | | | | X X | | | | | | | | | | | | | | | | X | +---------+---------+---------+---------+---------+---------+---------+ | | tetrahe | 3 BP, 1 | \< | trigona | NH~3~ | A | | | dral | LP | 109.5° | l | | | | | | | | pyramid | PCl~3~ | X X | | | | | | al | | | | | | | | | | X | +---------+---------+---------+---------+---------+---------+---------+ | | tetrahe | 2 BP, 2 | \< | v-shape | H~2~O | A | | | dral | LP | 109.5° | d | | | | | | | | or bent | OF~2~ | X X | +---------+---------+---------+---------+---------+---------+---------+ | | tetrahe | 1 BP, 3 | 180° | linear | HCl | A -- X | | | dral | LP | | | | | +---------+---------+---------+---------+---------+---------+---------+ | 5 | trigona | 5 BP, 0 | 120° & | trigona | PCl~5~ | X | | | l | LP | 90° | l | | | | | bipyram | | | bipyram | | X \| X | | | idal | | | idal | | | | | | | | | | A | | | | | | | | | | | | | | | | \| X | | | | | | | | | | | | | | | | X | +---------+---------+---------+---------+---------+---------+---------+ | 6 | octahed | 6 BP, 0 | 90° | octahed | SF~6~ | X | | | ral | LP | | ral | | | | | | | | | | X \| X | | | | | | | | | | | | | | | | A | | | | | | | | | | | | | | | | X \| X | | | | | | | | | | | | | | | | X | +---------+---------+---------+---------+---------+---------+---------+ e.g., HOF~(l)~ **..** H **:** O **:** F **:** 2 BP and 2 LP, therefore HOF~(l)~ is v-shaped: **Note:** -- ions are treated in the same way, but square brackets are placed around the diagram with the charge placed in the upper right hand corner **--** double and triple bonds are treated as one group of electrons when using VSEPR theory, and most of those molecules take the same shape as their Lewis structure **[[Polar Molecules]]{.smallcaps}** **bond dipole** -- the electronegativity difference of two bonded atoms represented by an arrow pointing from the lower (∂+) to the higher (∂-) electronegativity **nonpolar molecule** -- a molecule that has either nonpolar bonds (≤0.5 Δ En) or polar bonds whose bond dipoles cancel to zero (i.e., VSEPR diagram is symmetrical) **polar molecule** -- a molecule that has polar bonds with dipoles that do not cancel to zero e.g., NH~3~ **..** N ^3.0^ ~2.1~ H H ~2.1~ therefore, it is a polar molecule H ~2.1~ **[[Intermolecular Forces]]{.smallcaps}** **intermolecular force** -- the force of attraction and repulsion between molecules; much weaker than covalent bonds **dipole-dipole force** -- a force of attraction due to the simultaneous attraction of one dipole by its surrounding dipoles **--** the more polar the molecules, the stronger the force -- the shape of the molecule also affect the dipole-dipole strength (i.e., closer together = stronger force) **London dispersion force** -- the simultaneous attraction of an electron by the positive nuclei in the surrounding molecules -- the greater the number of electrons per molecule, the stronger the force - As dipole-dipole force or London dispersion force increases, the boiling point increases, allowing you to predict relative boiling point, if one of the forces is the same between the two substances, or if both forces are moving in the same direction. **hydrogen bonding** -- the attraction of a hydrogen atom to a lone pair of electrons in N, O, or F atoms in adjacent molecules (possible because H has no valence e^-^ to "shield" nucleus) **....** H -- F **:** **\-\-\-\-\-\-\-\-\-\-\--** H -- F **:** **[[Structure and Properties of Crystalline Solids]]{.smallcaps}** +---------+---------+---------+---------+---------+---------+---------+ | **[Crys | **[Part | **[Forc | **[Prop | **[Exam | | | | tal]{.s | icles]{ | e/]{.sm | erties] | ples]{. | | | | mallcap |.smallc | allcaps | {.small | smallca | | | | s}** | aps}** | }** | caps}** | ps}** | | | | | | | | | | | | | | **[Bond | | | | | | | | ]{.smal | | | | | | | | lcaps}* | | | | | | | | * | | | | | +=========+=========+=========+=========+=========+=========+=========+ | | | | [Meltin | [Conduc | [Solubi | | | | | | g | -]{.sma | lity | | | | | | Point]{ | llcaps} | in | | | | | |.smallc | | Liquid/ | | | | | | aps} | [tivity | ]{.smal | | | | | | | ]{.smal | lcaps} | | | | | | | lcaps} | | | | | | | | | [Soluti | | | | | | | | on]{.sm | | | | | | | | allcaps | | | | | | | | } | | +---------+---------+---------+---------+---------+---------+---------+ | Ionic | ions | ionic | medium | yes | yes | NaCl, | | | | | | | | Na~3~PO | | | (+ and | | (higher | | | ~4~, | | | -) | | as | | | CaF~2~, | | | | | ionic | | | MgO, | | | | | charge | | | CuSO~4~ | | | | | increas | | | 5H~2~O | | | | | es, | | | | | | | | size of | | | | | | | | ion | | | | | | | | decreas | | | | | | | | es) | | | | +---------+---------+---------+---------+---------+---------+---------+ | Metalli | cations | metalli | high | yes | no | Pb, Fe, | | c | | c | | | | | | | | | (higher | | | Cu, Al, | |  | | mobile | valence | | | | | | | delocal | electro | | | | | | | ized | ns | | | | | | | electro | increas | | | | | | | ns, | es) | | | | | | | allowin | | | | | | | | g | | | | | | | | for | | | | | | | | conduct | | | | | | | | ion | | | | | | | | of heat | | | | | | | | and | | | | | | | | electri | | | | | | | | city) | | | | | +---------+---------+---------+---------+---------+---------+---------+ | Polar | molecul | London, | low | no | yes | PF~3~, | | Molecul | es | dipole- | | | | ICl, | | ar | | dipole, | (higher | | | CHCl~3~ | | | | hydroge | as | | | , | | | | n | number | | | H~2~O, | | | | | of | | | NH~3~, | | | | | electro | | | SO~3~ | | | | | ns, | | | | | | | | polarit | | | | | | | | y | | | | | | | | of | | | | | | | | molecul | | | | | | | | es, | | | | | | | | and | | | | | | | | presenc | | | | | | | | e | | | | | | | | of | | | | | | | | hydroge | | | | | | | | n | | | | | | | | bonds | | | | | | | | increas | | | | | | | | es) | | | | +---------+---------+---------+---------+---------+---------+---------+ | Nonpola | molecul | | | | no | inert | | r | es | | | | | gases, | | Molecul | or | | | | | diatomi | | ar | single | | | | | c | | | atoms | | | | | element | | | | | | | | s, | | | | | | | | CO~2~, | | | | | | | | CCl~4~, | | | | | | | | SF~6~, | | | | | | | | BF~3~ | +---------+---------+---------+---------+---------+---------+---------+ | Covalen | atoms | covalen | very | no | no | diamond | | t | | t | high | | | , | | Network | | | | | | SiC, | | Crystal | | (a 3-D | (meltin | | | AlN, | | | | arrange | g | | | BeO, | |  | | covalen | as | | | Mg~2~S | | | | t | strengt | | | | | | | bonds | h | | | | | | | between | of | | | | | | | atoms; | covalen | | | | | | | resulti | t | | | | | | | ng | bonds | | | | | | | in | increas | | | | | | | hardnes | e | | | | | | | s | ) | | | | | | | and | | | | | | | | high | | | | | | | | melting | | | | | | | | point) | | | | | +---------+---------+---------+---------+---------+---------+---------+ **[[Network Solids (aka "supermolecules")]]{.smallcaps}** [Allotropes of Carbon]{.smallcaps}: a\) **diamond** -- a 3-D network solid - - - a\) **graphite** -- a 2-D network solid - - - [Silica and the Silicates]{.smallcaps}: - silicon combines with oxygen to form silicon dioxide, SiO~2~ (silica) - it further reacts with metal compounds to produce metal silicates a\) **quartz** -- a 3-D network solid b\) **mica** -- a 2-D network solid c\) **asbestos** -- a 1-D network solid **[[Chapter 5: Thermochemistry]]{.smallcaps}** **thermochemistry** -- the study of the energy changes that accompany physical or chemical changes of matter **thermal energy** -- energy available from a substance as a result of the motion of its molecules **chemical system** -- a set of reactants and products under study, usually represented by a chemical equation **surroundings** -- all matter around the system that is capable of absorbing or releasing thermal energy **heat** -- amount of energy transferred between substances **exothermic** -- releasing thermal energy as heat flows out of the system; negative molar enthalpy **endothermic** -- absorbing thermal energy as heat flows into the system; positive molar enthalpy **temperature** -- average kinetic energy of the particles in a sample of matter **open system** -- one in which both matter and energy can move