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

    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</p> Signup and view all the answers

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

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

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

    <p>False</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%</p> Signup and view all the answers

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

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

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

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

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

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

    Structural isomers must have different molecular formulas.

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

    What characterizes the addition of HCN to aldehydes and ketones?

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

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

    <p>False</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.</p> Signup and view all the answers

    The carbonyl group in aldehydes and ketones is sp3 hybridized.

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

    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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