ORGANIC CHEMISTRY SOLUTIONS MANUAL
ORGANIC CHEMISTRY SOLUTIONS MANUAL
5th Edition
ISBN: 9781260367546
Author: SMITH
Publisher: MCG CUSTOM
Question
Chapter 24, Problem 24.1P
Interpretation Introduction

(a)

Interpretation: The aldol product that formed by the given compound is to be drawn.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone. It is necessary that the carbonyl compound must contain at least one αhydrogen atom to undergo aldol reaction.

Expert Solution
Check Mark

Answer to Problem 24.1P

The aldol product that formed by the given compound is 3hydroxy2,4diphenylbutanal as shown below.

ORGANIC CHEMISTRY SOLUTIONS MANUAL, Chapter 24, Problem 24.1P , additional homework tip  1

Explanation of Solution

The aldol product that formed by the given compound is shown below.

ORGANIC CHEMISTRY SOLUTIONS MANUAL, Chapter 24, Problem 24.1P , additional homework tip  2

Figure 1

In this aldol reaction, one equivalent of 2phenylacetaldehyde is treated with strong base that results in the formation of resonance-stabilized enolate ion. The second equivalent of 2phenylacetaldehyde is then reacts with enolate ion. After that, hydrolysis of the intermediate compound takes place that results the formation of the desired product, 3hydroxy2,4diphenylbutanal.

Conclusion

The aldol product that formed by the given compound is 3hydroxy2,4diphenylbutanal.

Interpretation Introduction

(b)

Interpretation: The aldol product that formed by the given compound is to be drawn.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone. It is necessary that the carbonyl compound must contain at least one αhydrogen atom to undergo aldol reaction.

Expert Solution
Check Mark

Answer to Problem 24.1P

The aldol product that formed by the given compound is 2(tertbutyl)3hydroxy5,5dimethylhexanal as shown below.

ORGANIC CHEMISTRY SOLUTIONS MANUAL, Chapter 24, Problem 24.1P , additional homework tip  3

Explanation of Solution

The aldol product that formed by the given compound is shown below.

ORGANIC CHEMISTRY SOLUTIONS MANUAL, Chapter 24, Problem 24.1P , additional homework tip  4

Figure 2

In this aldol reaction, one equivalent of 3,3dimethylbutanal is treated with strong base that results in the formation of resonance-stabilized enolate ion. The second equivalent of 3,3dimethylbutanal is then reacts with enolate ion. After that, hydrolysis of the intermediate compound takes place that results the formation of the desired product, 2(tertbutyl)3hydroxy5,5dimethylhexanal.

Conclusion

The aldol product that formed by the given compound is 2(tertbutyl)3hydroxy5,5dimethylhexanal.

Interpretation Introduction

(c)

Interpretation: The aldol product that formed by the given compound is to be drawn.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone. It is necessary that the carbonyl compound must contain at least one αhydrogen atom to undergo aldol reaction.

Expert Solution
Check Mark

Answer to Problem 24.1P

The aldol product that formed by the given compound is 4hydroxy4methylpentan2one as shown below.

ORGANIC CHEMISTRY SOLUTIONS MANUAL, Chapter 24, Problem 24.1P , additional homework tip  5

Explanation of Solution

The aldol product that formed by the given compound is shown below.

ORGANIC CHEMISTRY SOLUTIONS MANUAL, Chapter 24, Problem 24.1P , additional homework tip  6

Figure 3

In this aldol reaction, one equivalent of propane2one is treated with strong base that results in the formation of resonance-stabilized enolate ion. The second equivalent of propane2one is then reacts with enolate ion. After that, hydrolysis of the intermediate compound takes place that results the formation of the desired product, 4hydroxy4methylpentan2one.

Conclusion

The aldol product that formed by the given compound is 4hydroxy4methylpentan2one.

Interpretation Introduction

(d)

Interpretation: The aldol product that formed by the given compound is to be drawn.

Concept introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone. It is necessary that the carbonyl compound must contain at least one αhydrogen atom to undergo aldol reaction.

Expert Solution
Check Mark

Answer to Problem 24.1P

The aldol product that formed by the given compound is 1'hydroxy[1,1'bi(cyclohexan)]2one as shown below.

ORGANIC CHEMISTRY SOLUTIONS MANUAL, Chapter 24, Problem 24.1P , additional homework tip  7

Explanation of Solution

The aldol product that formed by the given compound is shown below.

ORGANIC CHEMISTRY SOLUTIONS MANUAL, Chapter 24, Problem 24.1P , additional homework tip  8

Figure 4

In this aldol reaction, one equivalent of cyclohexanone is treated with strong base that results in the formation of resonance-stabilized enolate ion. The second equivalent of cyclohexanone is then reacts with enolate ion. After that, hydrolysis of the intermediate compound takes place that results the formation of the desired product, 1'hydroxy[1,1'bi(cyclohexan)]2one.

Conclusion

The aldol product that formed by the given compound is 1'hydroxy[1,1'bi(cyclohexan)]2one.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
Students have asked these similar questions
Draw a stepwise mechanism for the following Friedel–Crafts acylation.
Draw a stepwise mechanism for the following reduction.
β-Vetivone is isolated from vetiver, a perennial grass that yields a variety ofcompounds used in traditional eastern medicine, pest control, and fragrance. In one synthesis, ketone A is converted to β-vetivone by a two-step process: Michael reaction, followed by intramolecular aldol reaction. (a) What Michael acceptor is needed for the conjugate addition? (b) Draw a stepwise mechanism for the aldol reaction, which forms the six-membered ring.

Chapter 24 Solutions

ORGANIC CHEMISTRY SOLUTIONS MANUAL

Ch. 24 - Prob. 24.11PCh. 24 - Prob. 24.12PCh. 24 - Prob. 24.13PCh. 24 - Prob. 24.14PCh. 24 - Prob. 24.15PCh. 24 - Problem 24.16 What ester is formed when each...Ch. 24 - Prob. 24.17PCh. 24 - Prob. 24.18PCh. 24 - Draw the products of each reaction. a. b. Ch. 24 - Problem 24.20 Two steps in a synthesis of the...Ch. 24 - Prob. 24.21PCh. 24 - Problem 24.22 Which of the following compounds can...Ch. 24 - Prob. 24.23PCh. 24 - Problem 24.24 What starting materials are needed...Ch. 24 - Problem 24.25 Draw the products when each pair of...Ch. 24 - Prob. 24.26PCh. 24 - Problem 24.27 What starting materials are needed...Ch. 24 - Prob. 24.28PCh. 24 - 24.29 What steps are needed to convert A to B? Ch. 24 - Prob. 24.30PCh. 24 - 24.31 Draw the product formed in each directed...Ch. 24 - Prob. 24.32PCh. 24 - 24.33 What starting materials are needed to...Ch. 24 - Prob. 24.34PCh. 24 - Prob. 24.35PCh. 24 - 24.36 Identify the structures of C and D in the...Ch. 24 - Prob. 24.37PCh. 24 - Prob. 24.38PCh. 24 - 24.39 Draw the product formed from a Claisen...Ch. 24 - Prob. 24.40PCh. 24 - 24.41 Even though B contains three ester groups, a...Ch. 24 - Prob. 24.42PCh. 24 - Prob. 24.43PCh. 24 - 24.44 Vetivone is isolated from vetiver, a...Ch. 24 - Draw the product of each Robinson annulation from...Ch. 24 - Prob. 24.46PCh. 24 - 24.47 Draw the organic products formed in each...Ch. 24 - 24.48 Fill in the lettered reagents needed for...Ch. 24 - Prob. 24.49PCh. 24 - Prob. 24.50PCh. 24 - Prob. 24.51PCh. 24 - 24.52 Draw a stepwise mechanism for the following...Ch. 24 - Prob. 24.53PCh. 24 - Prob. 24.54PCh. 24 - Prob. 24.55PCh. 24 - Prob. 24.56PCh. 24 - Prob. 24.57PCh. 24 - Prob. 24.58PCh. 24 - Prob. 24.59PCh. 24 - 24.60 Devise a synthesis of each compound from the...Ch. 24 - 24.61 Devise a synthesis of each compound from...Ch. 24 - 24.62 Devise a synthesis of each compound from ,...Ch. 24 - Prob. 24.63PCh. 24 - Prob. 24.64PCh. 24 - 24.65 Answer the following questions about...Ch. 24 - Prob. 24.66PCh. 24 - Prob. 24.67PCh. 24 - Prob. 24.68PCh. 24 - 24.69 Devise a stepwise mechanism for the...Ch. 24 - 24.70 Draw a stepwise mechanism for the following...Ch. 24 - Prob. 24.71PCh. 24 - Prob. 24.72PCh. 24 - Prob. 24.73P
Knowledge Booster
Recommended textbooks for you
  • Chemistry
    Chemistry
    ISBN:9781305957404
    Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
    Publisher:Cengage Learning
    Chemistry
    Chemistry
    ISBN:9781259911156
    Author:Raymond Chang Dr., Jason Overby Professor
    Publisher:McGraw-Hill Education
    Principles of Instrumental Analysis
    Chemistry
    ISBN:9781305577213
    Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
    Publisher:Cengage Learning
  • Organic Chemistry
    Chemistry
    ISBN:9780078021558
    Author:Janice Gorzynski Smith Dr.
    Publisher:McGraw-Hill Education
    Chemistry: Principles and Reactions
    Chemistry
    ISBN:9781305079373
    Author:William L. Masterton, Cecile N. Hurley
    Publisher:Cengage Learning
    Elementary Principles of Chemical Processes, Bind...
    Chemistry
    ISBN:9781118431221
    Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
    Publisher:WILEY
  • Chemistry
    Chemistry
    ISBN:9781305957404
    Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
    Publisher:Cengage Learning
    Chemistry
    Chemistry
    ISBN:9781259911156
    Author:Raymond Chang Dr., Jason Overby Professor
    Publisher:McGraw-Hill Education
    Principles of Instrumental Analysis
    Chemistry
    ISBN:9781305577213
    Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
    Publisher:Cengage Learning
    Organic Chemistry
    Chemistry
    ISBN:9780078021558
    Author:Janice Gorzynski Smith Dr.
    Publisher:McGraw-Hill Education
    Chemistry: Principles and Reactions
    Chemistry
    ISBN:9781305079373
    Author:William L. Masterton, Cecile N. Hurley
    Publisher:Cengage Learning
    Elementary Principles of Chemical Processes, Bind...
    Chemistry
    ISBN:9781118431221
    Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
    Publisher:WILEY