Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
Question
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Chapter 16, Problem 16.14P

(a)

Interpretation Introduction

Interpretation:

The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Naming Aldehydes:

Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.

The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".

For example:

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  1

Naming Ketones:

The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".

Only few ketones have common name.

For example:

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  2

Naming of compounds with two functional groups,

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  ClassSuffix namePrefix nameCarboxylic acid-oic acidCarboxyEster-oateAlkoxy carbonylAmide-amideAmidoNitrile-ntrileCyanoAldehyde-alOxo(=O)Aldehyde-alFormyl(-CH=O)Ketone-oneOxo(=O)Alcohol-olHydroxyAmine-amineAminoAlkene-eneAlkenylAlkyne-yneAlkynylAlkane-aneAlkylEther---AlkoxyAlkylhalide---Halo

(a)

Expert Solution
Check Mark

Explanation of Solution

The given compound is as follows.

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  3

Let’s given numbering to this compound as follows,

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  4

The parent chain contains 9 carbon atoms; in the fifth carbon atom a ketone functional group is attached.

Thus, according to IUPAC this compound can be named as 5-Nonanone.

(b)

Interpretation Introduction

Interpretation:

The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Naming Aldehydes:

Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.

The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".

For example:

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  5

Naming Ketones:

The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".

Only few ketones have common name.

For example:

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  6

Naming of compounds with two functional groups,

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  ClassSuffix namePrefix nameCarboxylic acid-oic acidCarboxyEster-oateAlkoxy carbonylAmide-amideAmidoNitrile-ntrileCyanoAldehyde-alOxo(=O)Aldehyde-alFormyl(-CH=O)Ketone-oneOxo(=O)Alcohol-olHydroxyAmine-amineAminoAlkene-eneAlkenylAlkyne-yneAlkynylAlkane-aneAlkylEther---AlkoxyAlkylhalide---Halo

R and S nomenclature: it is used to assign the molecule using CIP (Cahn-Ingold-Prelog) rules.

The CIP rules are as follows:

Select the chiral carbon and assign the numbers according to the decreasing atomic mass of atoms attached to it.

If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.

(b)

Expert Solution
Check Mark

Explanation of Solution

The given compound is as follows.

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  7

Let’s write give the numbering to this compound.

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  8

This parent ring has five carbon atoms; a methyl group was attached to the second carbon atom.  Therefore, according to the IUPAC rules, the compound can be named as 2-methylcyclopentanone

Here, this compound has a chiral center (it is highlighted as *); its configuration can be specified as follows,

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  9

The numbering follows an anti-clock wise direction and so molecule is in as S configuration.

Thus, the compound name can be written as (S)-2-methylcyclopentanone

(c)

Interpretation Introduction

Interpretation:

The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Naming Aldehydes:

Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.

The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".

For example:

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  10

Naming Ketones:

The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".

Only few ketones have common name.

For example:

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  11

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  ClassSuffix namePrefix nameCarboxylic acid-oic acidCarboxyEster-oateAlkoxy carbonylAmide-amideAmidoNitrile-ntrileCyanoAldehyde-alOxo(=O)Aldehyde-alFormyl(-CH=O)Ketone-oneOxo(=O)Alcohol-olHydroxyAmine-amineAminoAlkene-eneAlkenylAlkyne-yneAlkynylAlkane-aneAlkylEther---AlkoxyAlkylhalide---Halo

(c)

Expert Solution
Check Mark

Explanation of Solution

The given compound is as follows.

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  12

Let’s give the numbering to the given compound.

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  13

The parent hydrocarbon chain has two functional groups and they are alkene (C=C) and aldehyde (CHO). According to IUPAC the aldehyde group has higher priority. Thus the compound can be named as 2-Methyl-2-butenal.

(d)

Interpretation Introduction

Interpretation:

The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Naming Aldehydes:

Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.

The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".

For example:

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  14

Naming Ketones:

The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".

Only few ketones have common name.

For example:

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  15

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  ClassSuffix namePrefix nameCarboxylic acid-oic acidCarboxyEster-oateAlkoxy carbonylAmide-amideAmidoNitrile-ntrileCyanoAldehyde-alOxo(=O)Aldehyde-alFormyl(-CH=O)Ketone-oneOxo(=O)Alcohol-olHydroxyAmine-amineAminoAlkene-eneAlkenylAlkyne-yneAlkynylAlkane-aneAlkylEther---AlkoxyAlkylhalide---Halo

R and S nomenclature: it is used to assign the molecule using CIP (Cahn-Ingold-Prelog) rules.

The CIP rules are as follows:

Select the chiral carbon and assign the numbers according to the decreasing atomic mass of atoms attached to it.

If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.

(d)

Expert Solution
Check Mark

Explanation of Solution

The given compound is as follows.

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  16

Let’s write give the numbering to this compound.

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  17

This parent chain has three carbon atoms; a methyl group was attached to the second carbon atom and hydroxyl group was attached to the third carbon atom.  Therefore, according to the IUPAC rules, the compound can be named as 3-Hydroxy-2-methyl-propanal.

Here, this compound has a chiral center (it is highlighted as *); its configuration can be specified as follows,

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  18

The numbering of substituents on the chiral center follows clock wise direction and so molecule is in R configuration.

Thus, the compound name can be written as (R)-3-Hydroxy-2-methyl-propanal.

(e)

Interpretation Introduction

Interpretation:

The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Naming Aldehydes:

Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.

The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".

For example:

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  19

Naming Ketones:

The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".

Only few ketones have common name.

For example:

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  20

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  ClassSuffix namePrefix nameCarboxylic acid-oic acidCarboxyEster-oateAlkoxy carbonylAmide-amideAmidoNitrile-ntrileCyanoAldehyde-alOxo(=O)Aldehyde-alFormyl(-CH=O)Ketone-oneOxo(=O)Alcohol-olHydroxyAmine-amineAminoAlkene-eneAlkenylAlkyne-yneAlkynylAlkane-aneAlkylEther---AlkoxyAlkylhalide---Halo

(e)

Expert Solution
Check Mark

Explanation of Solution

The given compound is as follows.

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  21

Let’s give the numbering to the given compound.

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  22

A phenyl ring is attached to the first carbon atom in the three membered parent carbon chains. According to IUPAC the aldehyde group has higher priority. Thus the compound can be named as 1-phenyl-1-propanone.

(f)

Interpretation Introduction

Interpretation:

The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Naming Aldehydes:

Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.

The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".

For example:

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  23

Naming Ketones:

The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".

Only few ketones have common name.

For example:

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  24

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  ClassSuffix namePrefix nameCarboxylic acid-oic acidCarboxyEster-oateAlkoxy carbonylAmide-amideAmidoNitrile-ntrileCyanoAldehyde-alOxo(=O)Aldehyde-alFormyl(-CH=O)Ketone-oneOxo(=O)Alcohol-olHydroxyAmine-amineAminoAlkene-eneAlkenylAlkyne-yneAlkynylAlkane-aneAlkylEther---AlkoxyAlkylhalide---Halo

R and S nomenclature: it is used to assign the molecule using CIP (Cahn-Ingold-Prelog) rules.

The CIP rules are as follows:

Select the chiral carbon and assign the numbers according to the decreasing atomic mass of atoms attached to it.

If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.

(f)

Expert Solution
Check Mark

Explanation of Solution

The given compound is as follows.

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  25

Let’s write give the numbering to this compound.

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  26

This parent ring has six carbon atoms; a hydroxyl (–OH) and a phenyl ring were attached to the first and fifth carbon atoms in the parent chain respectively.  Therefore, according to the IUPAC rules, the compound can be named as 5-Hydroxy-1-phenyl-3-hexanone.

Here, this compound has a chiral center (it is highlighted as *); its configuration can be specified as follows,

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  27

The numbering follows an anti-clock wise direction and so molecule is in as S configuration.

Thus, the compound name can be written as (S)-5-Hydroxy-1-phenyl-3-hexanone.

(g)

Interpretation Introduction

Interpretation:

The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Naming Aldehydes:

Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.

The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".

For example:

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  28

Naming Ketones:

The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".

Only few ketones have common name.

For example:

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  29

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  ClassSuffix namePrefix nameCarboxylic acid-oic acidCarboxyEster-oateAlkoxy carbonylAmide-amideAmidoNitrile-ntrileCyanoAldehyde-alOxo(=O)Aldehyde-alFormyl(-CH=O)Ketone-oneOxo(=O)Alcohol-olHydroxyAmine-amineAminoAlkene-eneAlkenylAlkyne-yneAlkynylAlkane-aneAlkylEther---AlkoxyAlkylhalide---Halo

(g)

Expert Solution
Check Mark

Explanation of Solution

The given compound is as follows.

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  30

Let’s give the numbering to the given compound.

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  31

The parent hydrocarbon ring has five carbon atoms. A propyl group was attached to the second carbon atom in the ring and two ketone groups were present in first and third carbon atom respectively. Thus the compound can be named as 2-propyl-1,3-cyclopentanedione.

(h)

Interpretation Introduction

Interpretation:

The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Naming Aldehydes:

Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.

The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".

For example:

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  32

Naming Ketones:

The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".

Only few ketones have common name.

For example:

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  33

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  ClassSuffix namePrefix nameCarboxylic acid-oic acidCarboxyEster-oateAlkoxy carbonylAmide-amideAmidoNitrile-ntrileCyanoAldehyde-alOxo(=O)Aldehyde-alFormyl(-CH=O)Ketone-oneOxo(=O)Alcohol-olHydroxyAmine-amineAminoAlkene-eneAlkenylAlkyne-yneAlkynylAlkane-aneAlkylEther---AlkoxyAlkylhalide---Halo

(h)

Expert Solution
Check Mark

Explanation of Solution

The given compound is as follows.

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  34

Let’s give the numbering to the given compound.

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  35

The parent hydrocarbon chain has five carbon atoms with two aldehydes on both ends. Thus according to IUPAC the compound can be named as pentanedial.

(i)

Interpretation Introduction

Interpretation:

The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Naming Aldehydes:

Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.

The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".

For example:

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  36

Naming Ketones:

The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".

Only few ketones have common name.

For example:

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  37

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  ClassSuffix namePrefix nameCarboxylic acid-oic acidCarboxyEster-oateAlkoxy carbonylAmide-amideAmidoNitrile-ntrileCyanoAldehyde-alOxo(=O)Aldehyde-alFormyl(-CH=O)Ketone-oneOxo(=O)Alcohol-olHydroxyAmine-amineAminoAlkene-eneAlkenylAlkyne-yneAlkynylAlkane-aneAlkylEther---AlkoxyAlkylhalide---Halo

(i)

Expert Solution
Check Mark

Explanation of Solution

The given compound is as follows.

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  38

Let’s give the numbering to the given compound.

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  39

The parent hydrocarbon chain has two functional groups and they are bromine and ketone. According to IUPAC the bromine has higher priority. Thus the compound can be named as 2-bromo-3-pentanone.

Here, this compound has a chiral center (it is highlighted as *); its configuration can be specified as follows,

Organic Chemistry, Chapter 16, Problem 16.14P , additional homework tip  40

The numbering follows a clock wise direction and so molecule is in R configuration.

Thus, the compound name can be written as (R)-2-bromo-3-pentanone.

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One compound that contributes to the “seashore smell” at beaches in Hawai‘i is dictyopterene D', a component of a brown edible seaweed called limu lipoa. Hydrogenation of dictyopterene D' with excess H2 in the presence of a Pd catalyst forms butylcycloheptane. Ozonolysis with O3 followed by (CH3)2S forms CH2(CHO)2, HCOCH2CH(CHO)2, and CH3CH2CHO. What are possible structures of dictyopterene D'?
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Chapter 16 Solutions

Organic Chemistry

Ch. 16.8 - The given mechanism of transamination reaction is...Ch. 16.8 - Prob. DQCh. 16.8 - Prob. EQCh. 16.8 - The given mechanism of transamination reaction is...Ch. 16.9 - Predict the position of the following equilibrium.Ch. 16.9 - Draw a structural formula for the keto form of...Ch. 16.10 - Prob. 16.11PCh. 16.11 - What aldehyde or ketone gives these alcohols upon...Ch. 16.11 - Prob. 16.13PCh. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - The infrared spectrum of compound A, C6H12O, shows...Ch. 16 - Following are 1H-NMR spectra for compounds B...Ch. 16 - Draw structural formulas for the product formed by...Ch. 16 - Suggest a synthesis for the following alcohols...Ch. 16 - Show how to synthesize the following alcohol using...Ch. 16 - 1-Phenyl-2-butanol is used in perfumery. Show how...Ch. 16 - Prob. 16.22PCh. 16 - Draw structural formulas for (1) the...Ch. 16 - Show how to bring about the following conversions...Ch. 16 - Prob. 16.25PCh. 16 - Wittig reactions with the following -chloroethers...Ch. 16 - Prob. 16.27PCh. 16 - Prob. 16.28PCh. 16 - 5-Hydroxyhexanal forms a six-membered cyclic...Ch. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - Propose a mechanism to account for the formation...Ch. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - Show how to bring about the following conversion.Ch. 16 - A primary or secondary alcohol can be protected by...Ch. 16 - Prob. 16.37PCh. 16 - Prob. 16.38PCh. 16 - Prob. 16.39PCh. 16 - Prob. 16.40PCh. 16 - The following molecule belongs to a class of...Ch. 16 - When cis-2-decalone is dissolved in ether...Ch. 16 - Prob. 16.43PCh. 16 - Prob. 16.44PCh. 16 - The following bicyclic ketone has two -carbons and...Ch. 16 - Propose a mechanism for this reaction.Ch. 16 - The base-promoted rearrangement of an -haloketone...Ch. 16 - If the Favorskii rearrangement of...Ch. 16 - (R)-Pulegone, readily available from pennyroyal...Ch. 16 - (R)-Pulegone is converted to (R)-citronellic acid...Ch. 16 - Starting with cyclohexanone, show how to prepare...Ch. 16 - Show how to convert cyclopentanone to these...Ch. 16 - Prob. 16.53PCh. 16 - Prob. 16.54PCh. 16 - Prob. 16.55PCh. 16 - Following is the structural formula of Surfynol, a...Ch. 16 - Prob. 16.57PCh. 16 - Propose a mechanism for this isomerization.Ch. 16 - Starting with acetylene and 1-bromobutane as the...Ch. 16 - Prob. 16.60PCh. 16 - Prob. 16.61PCh. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - All rearrangements we have discussed so far have...Ch. 16 - In dilute aqueous base, (R)-glyceraldehyde is...Ch. 16 - Treatment of -D-glucose with methanol in the...Ch. 16 - Treating a Grignard reagent with carbon dioxide...Ch. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Write the products of the following sequences of...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Prob. 16.78PCh. 16 - Prob. 16.79PCh. 16 - Prob. 16.80PCh. 16 - Prob. 16.81P
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