Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition
Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition
8th Edition
ISBN: 9780134473178
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Question
Chapter 17, Problem 48P

(a)

Interpretation Introduction

Interpretation: The structure of given compounds has to be drawn.

ethylacetoacetate

Concept introduction: The CO2 group is attached to a carbon that is adjacent to a carbon, the CO2 group can be removed because the electrons left behind can be delocalized onto the carbonyl oxygen.

Carboxylate ion with a carbonyl group at the 3-position loses CO2 when they are heated. Loss of CO2 from a molecule is called decarboxylation.

(a)

Expert Solution
Check Mark

Answer to Problem 48P

The structure of ethyl acetoacetae is,

Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition, Chapter 17, Problem 48P , additional homework tip  1

Explanation of Solution

The name given compound ethyl acetoacetate ends with ate.  This means the given compound must contain an ester group.  The name of compound starts with ethyl group, this means ethyl group is attached to the oxygen of an ester group.  The acetone group is attached with the carbonyl carbon of an ester group.  The structure of ethyl acetoacetae is,

Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition, Chapter 17, Problem 48P , additional homework tip  2

(b)

Interpretation Introduction

Interpretation: The structure of given compounds has to be drawn.

α-methylmalonicacid

Concept introduction: The CO2 group is attached to a carbon that is adjacent to a carbon, the CO2 group can be removed because the electrons left behind can be delocalized onto the carbonyl oxygen.

Carboxylate ion with a carbonyl group at the 3-position loses CO2 when they are heated. Loss of CO2 from a molecule is called decarboxylation.

(b)

Expert Solution
Check Mark

Answer to Problem 48P

The structure of α-methylmalonic acid is,

Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition, Chapter 17, Problem 48P , additional homework tip  3

Explanation of Solution

The structure of malonic acid is two carboxylic acid is attached with a methyl group.  The structure of α-methylmalonic acid is one methyl group is attached with an α carbon of malonic acid.  The structure of α-methylmalonic acid is,

Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition, Chapter 17, Problem 48P , additional homework tip  4

(c)

Interpretation Introduction

Interpretation: The structure of given compounds has to be drawn.

β-keto ester

Concept introduction: The CO2 group is attached to a carbon that is adjacent to a carbon, the CO2 group can be removed because the electrons left behind can be delocalized onto the carbonyl oxygen.

Carboxylate ion with a carbonyl group at the 3-position loses CO2 when they are heated. Loss of CO2 from a molecule is called decarboxylation.

(c)

Expert Solution
Check Mark

Answer to Problem 48P

The structure of β-keto ester is,

Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition, Chapter 17, Problem 48P , additional homework tip  5

Explanation of Solution

The given compound β-keto ester contains a keto group and an ester group.  The structure of β-keto ester is,

Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition, Chapter 17, Problem 48P , additional homework tip  6

(d)

Interpretation Introduction

Interpretation: The structure of given compounds has to be drawn.

The carboxylic acid obtained from malonic ester synthesis when the alkyl halide is propyl bromide

Concept introduction: The CO2 group is attached to a carbon that is adjacent to a carbon, the CO2 group can be removed because the electrons left behind can be delocalized onto the carbonyl oxygen.

Carboxylate ion with a carbonyl group at the 3-position loses CO2 when they are heated. Loss of CO2 from a molecule is called decarboxylation.

(d)

Expert Solution
Check Mark

Answer to Problem 48P

The structure of enol form of cyclopentanone is,

Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition, Chapter 17, Problem 48P , additional homework tip  7

Explanation of Solution

The compound cyclopentanone contain a keto group.  After the keto enol tautomerism the keto compound converted into an alcohol and a double bond.  The structure of enol form of cyclopentanone is,

Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition, Chapter 17, Problem 48P , additional homework tip  8

(e)

Interpretation Introduction

Interpretation: The structure of given compounds has to be drawn.:

The structure of enol form of cyclopentanone

Concept introduction: The CO2 group is attached to a carbon that is adjacent to a carbon, the CO2 group can be removed because the electrons left behind can be delocalized onto the carbonyl oxygen.

Carboxylate ion with a carbonyl group at the 3-position loses CO2 when they are heated. Loss of CO2 from a molecule is called decarboxylation.

(e)

Expert Solution
Check Mark

Answer to Problem 48P

The structure of the carboxylic acid obtained from malonic ester synthesis by using propyl bromide is,

Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition, Chapter 17, Problem 48P , additional homework tip  9

Explanation of Solution

The proton removed from the alpha carbon of malonic ester by the base.  Then, there is a nucleophilic substitution reaction takes place between the propyl bromide and carbanion of malonic ester.  The third step is acidic hydrolysis of an ester to form carboxylic acid. The fourth step is decarboxylation of the compound to form the desired product.  The reaction and structure of given compound is,

Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition, Chapter 17, Problem 48P , additional homework tip  10

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Design a stepwise synthesis to convert cyclopentanone and 4-bromobutanal to hydroxy aldehyde A.
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Chapter 17 Solutions

Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition

Ch. 17.5 - Show how the following compounds can be prepared...Ch. 17.6 - What compound is formed when a dilute solution of...Ch. 17.7 - Prob. 13PCh. 17.7 - Prob. 14PCh. 17.7 - How many stereoisomers are obtained from each of...Ch. 17.7 - Prob. 16PCh. 17.8 - Prob. 17PCh. 17.9 - Prob. 18PCh. 17.9 - What reagents should be used to prepare the...Ch. 17.10 - Prob. 20PCh. 17.10 - What aldehyde or ketone would be obtained when...Ch. 17.11 - Prob. 22PCh. 17.11 - How could you prepare the following compound using...Ch. 17.12 - Prob. 25PCh. 17.12 - What two carbonyl compound are required for the...Ch. 17.12 - Propose a mechanism for the following reaction:Ch. 17.13 - Draw the products of the following reactions:Ch. 17.13 - Prob. 29PCh. 17.13 - Prob. 30PCh. 17.14 - Prob. 31PCh. 17.15 - Write the mechanism for the reaction of a...Ch. 17.15 - Prob. 33PCh. 17.15 - Prob. 34PCh. 17.15 - Draw the product of the reaction of each of the...Ch. 17.16 - Draw the product obtained by heating each pair of...Ch. 17.16 - What two carbonyl compounds are needed to...Ch. 17.17 - Prob. 38PCh. 17.18 - Prob. 39PCh. 17.18 - Prob. 40PCh. 17.19 - Prob. 41PCh. 17.20 - Prob. 43PCh. 17.21 - Propose a mechanism for the formation of...Ch. 17.21 - Prob. 45PCh. 17.21 - a. If the biosynthesis of palmitic acid were...Ch. 17.21 - Prob. 47PCh. 17 - Prob. 48PCh. 17 - Prob. 49PCh. 17 - Number the following compounds in order of...Ch. 17 - The 1H NMR chemical shifts of nitromethane,...Ch. 17 - Prob. 52PCh. 17 - Draw the products of the following reactions: a....Ch. 17 - A racemic mixture of 2-methyl-1-phenyl-1-butanone...Ch. 17 - Draw the products of the following reaction:Ch. 17 - Prob. 56PCh. 17 - Prob. 57PCh. 17 - In the presence of excess base and excess halogen,...Ch. 17 - Identify A-L. (Hint: A shows three singles in its...Ch. 17 - Using cyclopentanone as the reactant, show the...Ch. 17 - Show how 4-methyl-3-hexanol can be synthesized...Ch. 17 - Show how the following compound can be synthesized...Ch. 17 - Show how the following compounds can be prepared...Ch. 17 - Prob. 64PCh. 17 - Prob. 65PCh. 17 - Indicate how each of the following compounds can...Ch. 17 - Prob. 67PCh. 17 - The ketone whose 1H NMR spectrum is shown here was...Ch. 17 - Indicate how the following compounds can be...Ch. 17 - Compound A with molecular formula C6H10 has two...Ch. 17 - Prob. 71PCh. 17 - Draw the products of the following reactions:Ch. 17 - Prob. 73PCh. 17 - a. Show how the amino acid alanine can be...Ch. 17 - Show how the following compounds can be...Ch. 17 - Prob. 76PCh. 17 - Explain why the following bromoketone forms...Ch. 17 - Prob. 78PCh. 17 - A carboxylic arid is formed when an -haloketone...Ch. 17 - An , -unsaturated carbonyl compound can be...Ch. 17 - What carbonyl compounds are required to prepare a...Ch. 17 - Prob. 82PCh. 17 - A Cannizzaro reaction is the reaction of an...Ch. 17 - Propose a mechanism for each of the following...Ch. 17 - The following reaction is known as the benzoni...Ch. 17 - Prob. 86PCh. 17 - Prob. 87PCh. 17 - Prob. 88PCh. 17 - Prob. 89PCh. 17 - Prob. 90PCh. 17 - Propose a mechanism for the following reaction:Ch. 17 - What reagents are required to convert the reactant...Ch. 17 - Starting with bromocyclohexane, how can each of...Ch. 17 - Describe how the following compounds can be...Ch. 17 - Prob. 4PCh. 17 - Describe three ways to synthesize the following...Ch. 17 - Explain why 92% of 2.4-pentanedione exists as the...Ch. 17 - Describe how the following compound can be...Ch. 17 - Prob. 8PCh. 17 - Prob. 9PCh. 17 - Prob. 10PCh. 17 - Show how the following compounds can be...
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