ORGANIC CHEMISTRY-EBOOK>I<
ORGANIC CHEMISTRY-EBOOK>I<
9th Edition
ISBN: 9781305084414
Author: McMurry
Publisher: INTER CENG
Question
Book Icon
Chapter 22.SE, Problem 23MP
Interpretation Introduction

a)

ORGANIC CHEMISTRY-EBOOK>I<, Chapter 22.SE, Problem 23MP , additional homework tip  1

Interpretation:

Whether the ketone obtained by the decarboxylation of the optically active β- keto acid will be optically active or not is to be stated. A mechanism to explain the formation of the ketone is to be proposed.

Concept introduction:

The decarboxylation of a β- keto acid takes place through the formation of a planar enol intermediate which then tautomerizes to the keto form. If the β- keto acid is optically active and if the chiral centre is involved in the reaction, the ketone product will be racemic and optically inactive. If the chiral centre is not involved in the reaction then the optical activity is retained in the ketone product.

To state:

Whether the ketone obtained by the decarboxylation of the optically active β- keto acid will be optically active or not.

To propose:

A mechanism to explain the formation of the ketone.

Interpretation Introduction

b)

ORGANIC CHEMISTRY-EBOOK>I<, Chapter 22.SE, Problem 23MP , additional homework tip  2

Interpretation:

Whether the ketone obtained by the decarboxylation of the optically active β- keto acid will be optically active or not is to be stated. A mechanism to explain the formation of the ketone is to be proposed.

Concept introduction:

The decarboxylation of a β- keto acid takes place through the formation of a planar enol intermediate which then tautomerizes to the keto form. If the β- keto acid is optically active and if the chiral centre is involved in the reaction, the ketone product will be racemic and optically inactive. If the chiral centre is not involved in the reaction then the optical activity is retained in the ketone product.

To state:

Whether the ketone obtained by the decarboxylation of the optically active β- keto acid will be optically active or not.

To propose:

A mechanism to explain the formation of the ketone.

Blurred answer
Students have asked these similar questions
7:35 < Dji Question 19 of 22 5G 50% Submit What is the pH of a buffer made from 0.350 mol of HBrO (Ka = 2.5 × 10-9) and 0.120 mol of KBRO in 2.0 L of solution? | 1 2 3 ☑ 4 5 6 C 7 8 ☐ 9 +/- Tap here for additional resources ||| 0 ×10 Г
aw the major substitution products you would expect for the reaction shown below. If substitution would not occur at a significant rate under these conditions, check the box underneath the drawing area instead. Be sure you use wedge and dash bonds where necessary, for example to distinguish between major products. Note for advanced students: you can assume that the reaction mixture is heated mildly, somewhat above room temperature, but strong heat or reflux is not used. B C Br HO O Substitution will not occur at a significant rate. Explanation Check + Х Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessib
Complete the following reactions with the necessary reagents to complete the shown transformation. Example: 1. 2. ? 3. 018 Br OH Answer: H₂O, H2SO4, HgSO4

Chapter 22 Solutions

ORGANIC CHEMISTRY-EBOOK>I<

Ch. 22.7 - Draw a resonance structure of the acetonitrile...Ch. 22.7 - Why do you suppose ketone halogenations in acidic...Ch. 22.7 - Prob. 13PCh. 22.7 - Prob. 14PCh. 22.7 - Prob. 15PCh. 22.7 - Prob. 16PCh. 22.SE - Prob. 17VCCh. 22.SE - Prob. 18VCCh. 22.SE - Prob. 19VCCh. 22.SE - Prob. 20MPCh. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Prob. 23MPCh. 22.SE - In the Hell–Volhard–Zelinskii reaction, only a...Ch. 22.SE - Prob. 25MPCh. 22.SE - Nonconjugated , -unsaturated ketones, such as...Ch. 22.SE - Prob. 27MPCh. 22.SE - Using curved arrows, propose a mechanism for the...Ch. 22.SE - Prob. 29MPCh. 22.SE - One of the later steps in glucose biosynthesis is...Ch. 22.SE - The Favorskii reaction involves treatment of an...Ch. 22.SE - Treatment of a cyclic ketone with diazomethane is...Ch. 22.SE - Prob. 33MPCh. 22.SE - Amino acids can be prepared by reaction of alkyl...Ch. 22.SE - Amino acids can also be prepared by a two-step...Ch. 22.SE - Heating carvone with aqueous sulfuric acid...Ch. 22.SE - Identify all the acidic hydrogens (pKa 25) in the...Ch. 22.SE - Rank the following compounds in order of...Ch. 22.SE - Prob. 39APCh. 22.SE - Base treatment of the following , -unsaturated...Ch. 22.SE - Prob. 41APCh. 22.SE - Prob. 42APCh. 22.SE - Prob. 43APCh. 22.SE - Which, if any, of the following compounds can be...Ch. 22.SE - Prob. 45APCh. 22.SE - Prob. 46APCh. 22.SE - Prob. 47APCh. 22.SE - How might you convert geraniol into either ethyl...Ch. 22.SE - Prob. 49APCh. 22.SE - One way to determine the number of acidic...Ch. 22.SE - Prob. 51APCh. 22.SE - Prob. 52APCh. 22.SE - Prob. 53APCh. 22.SE - Prob. 54APCh. 22.SE - Prob. 55APCh. 22.SE - Prob. 56APCh. 22.SE - All attempts to isolate primary and secondary...Ch. 22.SE - How would you synthesize the following compounds...Ch. 22.SE - Prob. 59APCh. 22.SE - Prob. 60APCh. 22.SE - Prob. 61APCh. 22.SE - Prob. 62APCh. 22.SE - As far back as the 16th century, South American...Ch. 22.SE - The key step in a reported laboratory synthesis of...Ch. 22.SE - Prob. 65AP
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Text book image
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning