Organic Naming and Isomerism Chapter 3.1
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Questions and Answers

Which of the following compounds has the highest priority in the order of precedence?

  • Ketones
  • Carboxylic acids (correct)
  • Aldehydes
  • Alcohols

The suffix for ketones is -al.

False (B)

What is the suffix used for aldehydes?

-al

For compounds with five or more carbons, ketones require a number to indicate the position of the ______ bond.

<p>double</p> Signup and view all the answers

Match the following functional groups with their corresponding suffixes:

<p>Aldehyde = -al Ketone = -one Carboxylic acid = -oic acid Alcohol = -ol</p> Signup and view all the answers

What is the common name for CH3CH2CH2NHCH3?

<p>N-methylpropylamine (B)</p> Signup and view all the answers

In naming secondary amines, the smaller alkyl group is always preceded by an -N.

<p>True (A)</p> Signup and view all the answers

What is the IUPAC name for N,N-dimethylpropylamine?

<p>N,N-dimethylpropan-1-amine</p> Signup and view all the answers

In a nitrile, the CN group counts as the first _____ of the chain.

<p>carbon</p> Signup and view all the answers

Match the following amine names with their structures:

<p>N-methylpropylamine = CH3CH2CH2NHCH3 N-ethylethanamine = CH3CH2NHCH2CH3 N,N-dimethylpropylamine = CH3CH2CH2N(CH3)2 1,6-diaminohexane = H2N(CH2)6NH2</p> Signup and view all the answers

What is the correct IUPAC name for diethylamine?

<p>N,N-diethylamine (A)</p> Signup and view all the answers

In a tertiary amine, each alkyl group is not given an N.

<p>False (B)</p> Signup and view all the answers

What is the general naming convention for nitriles?

<p>End in -nitrile</p> Signup and view all the answers

What is the major product ratio when hydrogen bromide is added to an unsymmetrical alkene?

<p>90% (C)</p> Signup and view all the answers

The stereochemistry of a molecule has no effect on drug action.

<p>False (B)</p> Signup and view all the answers

What type of products can result from the addition of hydrogen bromide to an unsymmetrical alkene?

<p>Isomeric products</p> Signup and view all the answers

The addition of hydrogen bromide can lead to __________ products from an alkene.

<p>isomeric</p> Signup and view all the answers

Match the following terms with their descriptions:

<p>Major product = Product that forms in the greatest amount Minor product = Product that forms in lesser amount Stereochemistry = The study of the spatial arrangement of atoms Optical isomers = Isomers that differ in the arrangement of atoms around a chiral center</p> Signup and view all the answers

What significant effect did one enantiomer of thalidomide have?

<p>It caused birth defects (B)</p> Signup and view all the answers

Thalidomide was initially used in a pure form before revealing its different effects.

<p>False (B)</p> Signup and view all the answers

What is the primary harmful effect associated with one enantiomer of thalidomide?

<p>birth defects</p> Signup and view all the answers

The compound thalidomide has one enantiomer that acts as a useful ______.

<p>sedative</p> Signup and view all the answers

Match the following compounds with their associated effects:

<p>Thalidomide = Causes birth defects Ibuprofen = Pain reliever Enantiomer A of Thalidomide = Useful sedative Racemic mixture of Thalidomide = Contains both enantiomers</p> Signup and view all the answers

What is the correct name for the acyl chloride with the formula CH3C(=O)Cl?

<p>ethanoyl chloride (A)</p> Signup and view all the answers

Secondary and tertiary amides are named the same way as primary amides.

<p>False (B)</p> Signup and view all the answers

What suffix is added to the stem of an amide to indicate its structure?

<p>amide</p> Signup and view all the answers

Compounds with the same molecular formula but different structural arrangements are known as __________.

<p>isomers</p> Signup and view all the answers

Match the following types of isomerism with their definitions:

<p>Chain isomerism = Different arrangement of carbon skeletons Position isomerism = Different positions of functional groups Functional group isomerism = Different functional groups with the same formula Structural isomerism = Same molecular formula but different structures</p> Signup and view all the answers

Which of the following compounds is an example of functional group isomers?

<p>Butanoic acid and butanal (D)</p> Signup and view all the answers

Structural isomers must have different molecular formulas.

<p>False (B)</p> Signup and view all the answers

What alkyl group prefix is used when naming secondary or tertiary amides?

<p>N-</p> Signup and view all the answers

The suffix used in naming acyl chlorides is __________.

<p>oyl chloride</p> Signup and view all the answers

What is one type of structural isomerism where a different arrangement of the carbon skeleton occurs?

<p>Chain isomerism (D)</p> Signup and view all the answers

What characterizes the addition of HCN to aldehydes and ketones?

<p>It produces a racemate. (D)</p> Signup and view all the answers

The intermediate formed during the nucleophilic addition of HCN is optically active.

<p>False (B)</p> Signup and view all the answers

What type of reaction mechanism is involved in the addition of HBr to unsymmetrical alkenes?

<p>Electrophilic addition</p> Signup and view all the answers

The approach of CN- to the carbonyl group is ______, resulting in the formation of a racemic mixture.

<p>equally from both sides</p> Signup and view all the answers

Match the following reactions with their outcomes:

<p>Addition of HCN to aldehydes = Formation of a racemate Addition of HBr to unsymmetrical alkene = Formation of a racemate Nucleophilic addition = Optically inactive product</p> Signup and view all the answers

In the reaction of HCN with carbonyls, what happens to the carbonyl group's planar structure?

<p>It allows for equal attack from either side. (A)</p> Signup and view all the answers

The carbonyl group in aldehydes and ketones is sp3 hybridized.

<p>False (B)</p> Signup and view all the answers

What is the effect of using HBr on an unsymmetrical alkene?

<p>It produces a racemic mixture.</p> Signup and view all the answers

The product from the addition of HCN to aldehydes and ketones is __________ because of equal amounts of both enantiomers.

<p>a racemate</p> Signup and view all the answers

What type of species is CN- in the reaction with aldehydes?

<p>Nucleophile (D)</p> Signup and view all the answers

Flashcards

Naming Aldehydes

Aldehyde names end in -al, and the carbonyl group (C=O) is always on the first carbon of the chain.

Naming Ketones

Ketone names end in -one. If the ketone has 5 or more carbons, a number is needed to show the position of the C=O (carbonyl) group in the chain.

Suffix vs. Prefix (Organic Naming)

Highest priority functional groups (like carboxylic acids) take the suffix. Lower priority groups (like alkyl halides) take the prefix.

Double/Triple Bonds in Organic Naming

Double and triple C-C bonds use a prefix in the name, not a suffix.

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Priority Order in Organic Nomenclature

Carboxylic acids have the highest naming priority followed by (carboxylix acid derivative,nitrile,aldehydes,ketones,alcohols,amines,alkenes and halogenoalkanes) in that order.

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Naming Secondary Amines

Secondary amines with two alkyl groups attached to nitrogen have their alkyl groups named, followed by the shorter alkyl group prefixed with "N".

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Secondary Amines: Naming Conventions

If the alkyl chains are the same length, the 'N' prefix is omitted in the common naming system.

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Tertiary Amine Naming

Tertiary amines have each alkyl group named and prefixed with an 'N' for the position in the common naming style.

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Naming Nitriles

Nitrile compounds end in "nitrile", with the carbon of the CN group considered the first carbon in the chain.

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Naming 1,6-Diaminohexane

Two amine groups in a chain are named as "1,6-diaminohexane" or "hexane-1,6-diamine".

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Secondary Amine Positional Prefix

"N" serves as a prefix to indicate the alkyl group's position, especially when the alkyl groups are of different lengths.

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Amine Naming with Different Chains

The smaller alkyl substituent gets the 'N' prefix for secondary and tertiary amines.

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CN Group in Nitriles

The carbon atom of the CN group is considered the first carbon (C1) in the chain when naming nitriles.

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Acyl Chlorides

A class of organic compounds where a carboxylic acid's -OH group is replaced by a chlorine atom.

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Naming Acyl Chlorides

Replace the -oic acid ending with -oyl chloride in the name of the corresponding carboxylic acid.

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Amides

Organic compounds containing a carbonyl group bonded to a nitrogen atom.

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Naming Secondary/Tertiary Amides

Name the alkyl groups bonded to the nitrogen, and include the prefix "N-" for each alkyl group.

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Structural Isomers

Compounds with the same molecular formula but different structural arrangements (different structures).

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Chain Isomerism

A type of structural isomerism where the carbon chain differs in length or branching.

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Position Isomerism

A type of structural isomerism where a functional group is attached at different positions on a carbon chain.

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Functional Group Isomers

Compounds with the same molecular formula but different functional groups.

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Aldehydes/Ketones

Examples of functional group isomers (different functional groups but same chemical formula).

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Isomerism

The existence of two or more compounds with the same chemical formula but different structures.

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Markovnikov's Rule

In the addition of HX (HBr, HCl, etc.) to an unsymmetrical alkene, the hydrogen atom attaches to the carbon with the greater number of hydrogens already attached.

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Electrophilic Addition

A type of addition reaction in which an electrophile, an electron-seeking species, attacks a double or triple bond.

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Carbocation stability

Carbocations increase in stability with increasing substitution. Tertiary carbocations are the most stable.

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Stereoisomers

Molecules with the same molecular formula and connectivity but different spatial arrangements.

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Drug action and chirality

The specific three-dimensional shape of a drug molecule can determine its ability to bind to a target site and produce a biological effect.

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Optical Isomers and Effects

Different optical isomers of the same molecule can have drastically different effects on the body. For example, one enantiomer of Thalidomide may cause birth defects, while the other acts as a sedative.

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Thalidomide Tragedy

Thalidomide was initially marketed as a sedative but was later found to cause serious birth defects. This was because the drug was administered as a racemic mixture, containing both enantiomers, one of which was harmful.

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Racemic Mixture

A racemic mixture is a 50:50 mixture of two enantiomers. It's like having a bag with an equal number of left and right hands.

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Chiral Carbon

A carbon atom attached to four different groups is called a chiral carbon. This creates the possibility of two non-superimposable mirror images (enantiomers).

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Enantiomer

An enantiomer is one of two mirror image isomers that cannot be superimposed. They are like left and right hands, they are mirror images but cannot be placed on top of each other.

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Racemate

A mixture containing equal amounts of two enantiomers (mirror-image isomers).

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Nucleophilic Addition

A reaction where a nucleophile (electron-rich species) attacks an electrophile (electron-deficient species), forming a new bond.

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Why are aldehydes and ketones reactive?

Their carbonyl group (C=O) has a partially positive carbon, making it susceptible to nucleophilic attack.

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How does a racemate form in nucleophilic addition?

When the carbonyl group is attacked equally from both sides by the nucleophile, it results in the formation of two enantiomers in equal amounts.

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What is optical activity?

The ability of a substance to rotate plane-polarized light.

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Can a racemate be optically active?

No, racemates are not optically active because the rotation caused by one enantiomer is cancelled out by the rotation caused by the other.

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How does a racemate form in electrophilic addition?

The attack of a nucleophile (like Br-) on a planar carbocation can occur from both sides, resulting in the formation of two enantiomers in equal amounts.

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What are enantiomers?

Stereoisomers that are non-superimposable mirror images of each other.

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What are stereoisomers?

Isomers that have the same molecular formula and connectivity but differ in the arrangement of atoms in space.

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What is a carbocation?

A positively charged carbon atom with only three bonds.

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Study Notes

Organic Naming and Isomerism

  • Refer to chapter 3.1 for basic organic molecule naming.
  • This chapter expands on naming functional groups discussed in subsequent chapters.

Homologous Series

  • Aldehydes: Suffix -al, prefix formyl-
  • Example: Ethanal
  • Ketones: Suffix -one, prefix oxo-
  • Example: Propanone
  • Carboxylic Acids: Suffix -oic acid
  • Example: Ethanoic acid
  • Nitriles: Suffix -nitrile, prefix cyano-
  • Example: Propanenitrile
  • Amines: Suffix -amine, prefix amino-
  • Example: Propylamine (or propan-1-amine)
  • Esters: Suffix -oate
  • Example: Methylethanoate
  • Amide: Suffix -amide
  • Example: Ethanamide
  • Acid Anhydrides: Suffix -oic anhydride
  • Example: Ethanoic anhydride
  • Acyl Chlorides: Suffix -oyl chloride
  • Example: Ethanoyl chloride

Priority Order for Naming

  • When several functional groups are present, the group with highest priority is given the suffix and lowest position on the carbon chain.
  • Highest priority (first): Carboxylic acids > carboxylic acid derivatives > nitriles > aldehydes > ketones > alcohols > amines > alkenes > halogenoalkanes
  • Lower priority groups are named as prefixes.
  • Double or triple C-C bonds only take suffix form if they aren't lower priority than another functional group

Aldehydes

  • Aldehydes end in -al.
  • The C=O bond is always on the first carbon of the chain.
  • No extra number is needed for the position of the aldehyde group on the chain.

Ketones

  • Ketones end in -one.
  • If the chain has 5+ carbons, a number is needed to indicate the ketone group's position in the chain.
  • If there are two ketone groups, the prefix "di" is used before '-one' and 'e' is added to the stem.

Carboxylic Acids

  • Carboxylic acids end in -oic acid.
  • No number is needed for the position of the acid group, as it is always at the end of the chain.

Amines

  • Amines end in -amine.
  • Two ways of naming: common or using locants.
  • If there is another higher-priority functional group, prefix "amino" is used to indicate the amine's location.
  • Secondary amines have two alkyl groups on the nitrogen, and teritary amines have three are named differently to show those different alkyl groups.
  • Smaller is named as a prefix for secondary and tertiary amides.

Functional Groups

  • Naming functional groups is key when molecules contain multiple functional groups.
  • Groups with higher priority are named using suffixes.

Isomers

  • Structural Isomers: Same molecular formula, different structures.
    • Chain isomerism
    • Position isomerism
    • Functional group isomerism
  • Stereoisomers: Same structural formula, different spatial arrangement of atoms.
    • Geometric (E/Z) and optical isomers
  • Optical isomers: Asymmetric carbon (4 distinct groups attached) that rotate plane-polarized light either clockwise (+) or counterclockwise (-).
    • Enantiomers are mirror images.
    • Racemic mixture is a 50/50 mix of enantiomers.

Stereoisomers

  • Stereochemistry: Same structural formula, but atoms arranged differently in space.
  • Geometrical Isomers: Different spatial arrangement around a double bond.
  • Optical Isomers: Four different groups attached to a carbon, mirror-image isomers non-superimposable, rotate plane-polarized light, either D or L

Chemical Reactions and Optical Isomers

  • A racemic mixture forms when a reactant or intermediate has a trigonal planar group. Equal chance for either enantiomer formation.
  • Nucleophilic addition of HCN to aldehydes/ketones can lead to racemates, similarly addition of HBr to alkenes.
  • Drug action is often influenced by stereochemistry, with different enantiomers leading to different effects.

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Organic Naming and Isomerism Revision Guide PDF

Description

This quiz covers the basics of organic molecule naming and dives into the naming of various functional groups. It builds on the concepts discussed in Chapter 3.1, emphasizing the importance of understanding homologous series and priority order for naming. Test your knowledge of aldehydes, ketones, carboxylic acids, and more!

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