28 Questions
What is the correct order of steps in naming an ether according to IUPAC rules?
Name the two alkyl substituents and then write the suffix (ether)
What is the main reason for the lower boiling points of ethers compared to alcohols?
The weaker intermolecular forces between ether molecules
Which of the following ethers is soluble in water?
Dimethyl ether
What is the general formula for an aldehyde?
R-CHO
What is the reason for the fairly unreactive nature of ethers?
The nonpolar nature of ethers
What is the effect of electropositive carbonyl carbon on the O—H bond?
It pulls electrons away from the O—H bond
What is the pKa value of F3CCOOH?
0.23
What is the general formula of an ester?
R—COO—R*
How do you name an ester in IUPAC nomenclature?
Prefix for the alcohol side, suffix for the acid side
What is the general formula of an amine?
R—N(R*)2
What is the effect of Cr(VI) reagents on primary alcohols and aldehydes?
They oxidize them to form carboxylic acids
What is the correct order of naming an amine according to IUPAC rules?
names of all alkyl substituents linked to the N atom followed by the suffix (amine)
Why do tertiary amines have a lower boiling point compared to primary and secondary amines?
They cannot form hydrogen bonds
What is the result of reacting a primary amine with a large excess of NH3?
Formation of the primary amine
What is the reason behind the solubility of small amines in water?
They can accept hydrogen bonds from water
What is the product of the reaction between a primary amine and an acid halide?
An amide
What type of compound is obtained when a secondary ROH is oxidized?
Ketone
What is a functional group responsible for in an organic molecule?
Center of reactivity
Which type of hydration of alkynes yields aldehydes?
Anti-Markovnikov hydration
What is the general formula of carboxylic acids, where R is a hydrogen or hydrocarbon group?
RCOOH
What is the general formula of alkyl halides?
R–X, where R is a hydrocarbon group and X is a halogen
Which IUPAC rule for carboxylic acids involves determining the longest continuous chain of carbon atoms starting from the carboxyl group?
Rule 1
What is the IUPAC rule for determining the parent name of an alkyl halide?
The longest continuous chain of carbon atoms that includes the halogen
What is the prefix used for two halogen substituents on a benzene ring in the 1,3- position?
m-
What is the reason for the higher boiling points of carboxylic acids compared to alkanes?
Polarity
What is the characteristic of the structure of carboxylic acids?
Planar sp2 hybridized
What is the general formula of alcohols?
R–OH, where R is a hydrocarbon group and OH is a hydroxyl group
What is the correct IUPAC name for the compound 1,2-dichlorobenzene?
o-dichlorobenzene
Study Notes
Ethers
- IUPAC nomenclature rules:
- Write names of two substituents alkyl linked to the O atom
- Write suffix (ether)
- Example: CH3‒O‒CH2CH3: ethyl methyl ether
- No hydrogen bonding is possible in R—O—R
- Boiling points are much lower than alcohols, similar to haloalkanes
- Water solubility is much less than alcohols
- MeOMe and EtOEt have some water solubility, but larger ethers are insoluble, similar to alkanes
- Fairly unreactive, nonpolar solvents for organic reactions
Aldehydes
- Organic compounds containing a carbonyl group (C=O) and at least one hydrogen atom bonded to the carbon in the carbonyl group
- General formula: RCHO, where R is a hydrocarbon (aliphatic or aromatic) group
- Electropositive carbonyl carbon pulls electrons away from O—H bond
- Resulting carboxylate anion is stabilized by resonance
- Electron withdrawing substituents increase acidity
- Carboxylate anion is named as an alkanoate (e.g., formate, acetate, pentanoate)
Synthesis of Carboxylic Acids
- Oxidation of primary alcohols and aldehydes by Cr(VI) reagents
- Reaction of carboxylic acid: ester formation
Esters
- Organic compounds derived from carboxylic acid and alcohol
- General formula: RCOOR*, where R is a hydrogen or hydrocarbon (aliphatic or aromatic) group, and R* is a hydrocarbon group
- IUPAC nomenclature rules:
- Write suitable prefix for #C, then suffix (….yl) for the side derived from alcohol
- Write suitable prefix for #C, then suffix (….anoate) for the side derived from carboxylic acid
- Example: Methyl methanoate, Ethyl butanoate
Amines
- Organic compounds containing the C–N linkage
- General formula: RNH2, R2NH, or R3N, where R is a hydrocarbon group, R* and R** are a hydrogen or hydrocarbon (aliphatic or aromatic) group
- IUPAC nomenclature rules:
- Write names of all substituents alkyl linked to the N atom
- Write suffix (amine)
- Example: Ethyl amine, Dimethyl amine, Methyl propyl amine, Trimethyl amine
- Physical properties:
- N—H less polar than O—H
- Amines have lower boiling points than alcohols due to weaker hydrogen bonds
- Tertiary amines have lower boiling points than primary and secondary amines
- Small amines are soluble in water, branching increases solubility
- Most amines smell like rotting fish
Ketones
- Boiling points are higher than alkanes due to polarity
- Small carbonyl compounds (< 7 C) are water soluble due to polarity (e.g., acetone)
Oxidation of Alcohols
- Secondary ROH gives ketones
- Primary ROH gives aldehydes
Ozonolysis of Alkenes
- Yields ketones or aldehydes
Hydration of Alkynes
- Markovnikov hydration yields ketones
- Anti-Markovnikov hydration yields aldehydes
Carboxylic Acids
- Organic compounds containing the carboxyl group (–COOH)
- General formula: RCOOH, where R is a hydrogen or hydrocarbon (aliphatic or aromatic) group
- IUPAC nomenclature rules:
- Determine longest continuous chain of carbon atoms starting from carboxyl group (–COOH) (parent name)
- Put number for C atoms in the continuous chain of carbon starting from carboxyl group (–COOH)
- Put numbers and names of substituents alkyl
- Write suitable prefix for #C, then suffix (….anoic acid)
- Example: Methanoic acid, Ethanoic acid (formic acid, acetic acid)
- Planar sp2 hybridized structure
- Hydrogen bonded dimers
- Acid-base characteristics
Aromatic Compounds
- Functional group: a group of atoms responsible for the chemical behavior of the parent molecule
- Reactions of benzene: halogen substitution, nitro substitution
Alkyl Halides
- Organic compounds containing at least one carbon‒halogen (Cl, Br, I) bond
- General formula: R–X, where R is a hydrocarbon (aliphatic or aromatic) group, X is Cl, Br, or I
- IUPAC nomenclature rules:
- Determine longest continuous chain of carbon atoms in that pass with carbon which links up with halogen (parent name)
- Put number for C atoms in the continuous chain of carbon starting from terminal C which near to carbon‒halogen bond C‒X
- Put numbers and names of substituents alkyl
- Put number carbon which links up with halogen
- Put numbers and names of halogen as halo (chloro, bromo, iodo), if two halogen or more halogen use (di-, tri-, or tetra- ,…)
- Write suitable prefix for #C, then suffix (….ane)
- Example: Flouroethane, 1-iodopropane, 2-bromobutane, 2-bromo-3-methylpentane, 2,3-dichloropentane, 2,4-dibromopentane
- For two halogen substituents on benzene ring:
- Use prefixes o- (ortho-), m- (meta-), or p- (para-)
Learn about the rules of naming ethers according to IUPAC, including the correct order of substituents and suffixes. This quiz also covers the physical properties of ethers, such as their boiling points, water solubility, and hydrogen bonding characteristics.
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