ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL
ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL
8th Edition
ISBN: 9780134595450
Author: Bruice
Publisher: PEARSON
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Chapter 16, Problem 53P

Draw the structure for each of the following:

  1. a. isobutyraldehyde
  2. b. 4-hexenaI
  3. c. diisopentyl ketone
  4. d. 3-methylcyclohexanone
  5. e. 2.4-pentanedione
  6. f. 4-bromo-3-heptanone
  7. g. γ-bromocaproaldehyde
  8. h. 2-ethylcyclopentanecarbaldehyde
  9. i. 4-methyl-5-oxohexanal

(a)

Expert Solution
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Interpretation Introduction

Interpretation:

The structure of Isobutyraldehyde has to be drawn.

Answer to Problem 53P

The structure of Isobutyraldehyde is given below:

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL, Chapter 16, Problem 53P , additional homework tip  1

Explanation of Solution

The compound has aldehyde group that is attached to the isobutyl group.

The structure of isobutyraldehyde is as follows.

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL, Chapter 16, Problem 53P , additional homework tip  2

(b)

Expert Solution
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Interpretation Introduction

Interpretation:

The structure of 4-hexenal has to be drawn.

Answer to Problem 53P

The structure of 4-hexenal is given below:

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL, Chapter 16, Problem 53P , additional homework tip  3

Explanation of Solution

The compound has aldehyde functional group and double bond at the 4th position of the compound.

The structure is as follows.

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL, Chapter 16, Problem 53P , additional homework tip  4

(c)

Expert Solution
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Interpretation Introduction

Interpretation:

The structure of diisopentyl ketone has to be drawn.

Answer to Problem 53P

The structure of diisopentyl ketone is given below:

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL, Chapter 16, Problem 53P , additional homework tip  5

Explanation of Solution

The compound has ketone functional group.  Two isopentyl groups are attached to the keto group.

The structure of diisopentyl ketone is as follows.

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL, Chapter 16, Problem 53P , additional homework tip  6

(d)

Expert Solution
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Interpretation Introduction

Interpretation:

The structure of 3-methylcyclohexanone has to be drawn.

Answer to Problem 53P

The structure of 3-methylcyclohexanoneis given below:

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL, Chapter 16, Problem 53P , additional homework tip  7

Explanation of Solution

The compound has ketone functional and group and it is called as cyclohexanone and it has one methyl group at 3rd position of the ring.

The structure of 3-methyl cyclohexanone is as follows.

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL, Chapter 16, Problem 53P , additional homework tip  8

(e)

Expert Solution
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Interpretation Introduction

Interpretation:

The structure of 2,4-pentanedione has to be drawn.

Answer to Problem 53P

The structure of 2,4-pentanedione is given below:

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL, Chapter 16, Problem 53P , additional homework tip  9

Explanation of Solution

The compound has two keto functional groups and these are attached to the pentane carbon chain.

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL, Chapter 16, Problem 53P , additional homework tip  10

(f)

Expert Solution
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Interpretation Introduction

Interpretation:

The structure of 4-bromo-3-heptanone has to be drawn.

Answer to Problem 53P

The structure of 4-bromo-3-heptanone is given below:

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL, Chapter 16, Problem 53P , additional homework tip  11

Explanation of Solution

The compound has keto functional group and it is attached to the heptanes carbon chain.  At the 4th position of the carbon chain has bromine attachment.

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL, Chapter 16, Problem 53P , additional homework tip  12

(g)

Expert Solution
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Interpretation Introduction

Interpretation:

The structure of γ-Bromocaproaldehyde has to be drawn.

Answer to Problem 53P

The structure of γ-Bromocaproaldehyde is given below:

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL, Chapter 16, Problem 53P , additional homework tip  13

Explanation of Solution

Compound has aldehyde functional group and at the γ-position of the carbon chain has bromine.

The structure of γ-Bromocaproaldehyde are as follows.

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL, Chapter 16, Problem 53P , additional homework tip  14

(h)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structure of 2-ethylcyclopentanecarbaldehyde has to be drawn.

Answer to Problem 53P

The structure of 2-ethylcyclopentanecarbaldehyde is given below:

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL, Chapter 16, Problem 53P , additional homework tip  15

Explanation of Solution

In this compound, pentane ring has ethyl group and aldehyde functional group.

The structure of 2-ethylcyclopentane carbaldehyde.

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL, Chapter 16, Problem 53P , additional homework tip  16

(i)

Expert Solution
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Interpretation Introduction

Interpretation:

The structure of 4-methyl-5-oxohexanal has to be drawn.

Answer to Problem 53P

The structure of 4-methyl-5-oxohexanal is givenbelow:

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL, Chapter 16, Problem 53P , additional homework tip  17

Explanation of Solution

The compound has aldehyde functional group at the 5th position of the carbon chain as keto group it is named as oxo-because it is referred to an attachment.

The structure of 4- methyl-5-oxohexanal.

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL, Chapter 16, Problem 53P , additional homework tip  18

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Chapter 16 Solutions

ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL

Ch. 16.4 - Show how the following compounds can be...Ch. 16.4 - Prob. 13PCh. 16.4 - Prob. 14PCh. 16.4 - In the mechanism for cyanohydrin formation, why is...Ch. 16.4 - Prob. 16PCh. 16.4 - Prob. 17PCh. 16.4 - Show two ways to convert an alkyl halide into a...Ch. 16.5 - Prob. 20PCh. 16.5 - Prob. 21PCh. 16.5 - Prob. 22PCh. 16.5 - Prob. 23PCh. 16.6 - Prob. 24PCh. 16.7 - What reducing agents should be used to obtain the...Ch. 16.7 - Prob. 26PCh. 16.8 - Prob. 27PCh. 16.8 - Prob. 28PCh. 16.8 - Prob. 29PCh. 16.8 - The pKa of protonated acetone is about 7.5. and...Ch. 16.8 - Prob. 31PCh. 16.8 - Prob. 32PCh. 16.8 - Prob. 33PCh. 16.8 - Excess ammonia must be used when a primary amine...Ch. 16.8 - The compounds commonly known as amino acids are...Ch. 16.9 - Hydration of an aldehyde is also catalyzed by...Ch. 16.9 - Which ketone forms the most hydrate in an aqueous...Ch. 16.9 - When trichloroacetaldehyde is dissolved in water,...Ch. 16.9 - Which of the following are a. hermiacetals? b....Ch. 16.9 - Prob. 40PCh. 16.9 - Explain why an acetal can be isolated but most...Ch. 16.10 - Prob. 42PCh. 16.10 - Prob. 43PCh. 16.10 - What products would be formed from the proceedings...Ch. 16.10 - a. In a six-step synthesis, what is the yield of...Ch. 16.10 - Show how each of the following compounds could be...Ch. 16.12 - Prob. 47PCh. 16.13 - Prob. 49PCh. 16.14 - Prob. 50PCh. 16.15 - Prob. 51PCh. 16.16 - Prob. 52PCh. 16 - Draw the structure for each of the following: a....Ch. 16 - Prob. 54PCh. 16 - Prob. 55PCh. 16 - Prob. 56PCh. 16 - a. Show the reagents required to form the primary...Ch. 16 - Prob. 58PCh. 16 - Prob. 59PCh. 16 - Using cyclohexanone as the starting material,...Ch. 16 - Propose a mechanism for each of the following...Ch. 16 - Show how each of the following compounds can be...Ch. 16 - Fill in the boxes:Ch. 16 - Prob. 64PCh. 16 - Identify A through O:Ch. 16 - Prob. 66PCh. 16 - Prob. 67PCh. 16 - Prob. 68PCh. 16 - How many signals would the product of the...Ch. 16 - Prob. 70PCh. 16 - Prob. 71PCh. 16 - Prob. 72PCh. 16 - Prob. 73PCh. 16 - Prob. 74PCh. 16 - Prob. 75PCh. 16 - Prob. 76PCh. 16 - Prob. 77PCh. 16 - Prob. 78PCh. 16 - Draw structure for A-D for each of the following:Ch. 16 - Prob. 80PCh. 16 - a. Propose a mechanism for the following reaction:...Ch. 16 - Prob. 82PCh. 16 - A compound gives the following IR spectrum. Upon...Ch. 16 - How can be following compounds be prepared from...Ch. 16 - Prob. 85PCh. 16 - Prob. 86PCh. 16 - Prob. 87PCh. 16 - In the presence of an acid catalyst, acetaldehyde...Ch. 16 - Prob. 89PCh. 16 - Prob. 90PCh. 16 - Prob. 91PCh. 16 - A compound reacts with methylmagnesium bromide...Ch. 16 - Show how each of the following compounds can be...Ch. 16 - Prob. 94PCh. 16 - The pKa values of the carboxylic acid groups of...Ch. 16 - The Baylis-Hillman reaction is a DABCO...Ch. 16 - Prob. 97PCh. 16 - Prob. 98P
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