ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
9th Edition
ISBN: 9780137249442
Author: Wade
Publisher: INTER PEAR
Question
Book Icon
Chapter 22.12, Problem 22.36P

(a)

Interpretation Introduction

Interpretation:

The product of self-condensation of the given ester is to be predicted.

Concept introduction:

In the claisen-ester condensation, nucleophilic acyl substitution takes place on an ester. The enolate ion acts as a nucleophile. It attacks the carbonyl carbon to form a tetrahedral intermediate. Acidity of beta-keto ester products is higher than simple ketones, aldehydes and esters.

(b)

Interpretation Introduction

Interpretation:

The product of self-condensation of the given ester is to be predicted.

Concept introduction:

In the claisen-ester condensation, nucleophilic acyl substitution takes place on an ester. The enolate ion acts as a nucleophile. It attacks the carbonyl carbon to form a tetrahedral intermediate. Acidity of beta-keto ester products is higher than simple ketones, aldehydes and esters.

(c)

Interpretation Introduction

Interpretation:

The product of self-condensation of the given ester is to be predicted.

Concept introduction:

In the claisen-ester condensation, nucleophilic acyl substitution takes place on an ester. The enolate ion acts as a nucleophile. It attacks the carbonyl carbon to form a tetrahedral intermediate. Acidity of beta-keto ester products is higher than simple ketones, aldehydes and esters.

(d)

Interpretation Introduction

Interpretation:

The product of self-condensation of the given ester is to be predicted.

Concept introduction:

In the claisen-ester condensation, nucleophilic acyl substitution takes place on an ester. The enolate ion acts as a nucleophile. It attacks the carbonyl carbon to form a tetrahedral intermediate. Acidity of beta-keto ester products is higher than simple ketones, aldehydes and esters.

Blurred answer
Students have asked these similar questions
Redraw the tripeptide with or without its acidic hydrogensto demonstrate where the total charge of -2 comes from: *see image
2. Consider the data below to answer the following questions. Cyanohydrins are important intermediates in the synthesis of α-hydroxycarboxylic acids from ketones and aldehydes. The nitrile functional group can be hydrolyzed by aqueous acid to yield a carboxylic acid. Nitriles can also be hydrolyzed to carboxylic acids using aqueous base. Unfortunately, when a cyanohydrin is treated with aqueous base the original carbonyl compound is isolated. OH CH-COOH 0 HO CN C H30* C. H H HC N NaOH H₂O C=O 0 cyanohydrin H + NaCN + H₂O
Assign all integrated peaks

Chapter 22 Solutions

ORGANIC CHEMISTRY MASTERINGCHEM ACCESS

Ch. 22.5C - Acid-catalyzed halogenation is synthetically...Ch. 22.6 - Show the products of the reactions of these...Ch. 22.7A - Prob. 22.18PCh. 22.7A - Prob. 22.19PCh. 22.7A - Prob. 22.20PCh. 22.7B - Prob. 22.21PCh. 22.8 - Prob. 22.22PCh. 22.8 - Prob. 22.24PCh. 22.9 - Prob. 22.25PCh. 22.9 - Prob. 22.26PCh. 22.9 - Prob. 22.27PCh. 22.9 - Prob. 22.28PCh. 22.9 - Prob. 22.29PCh. 22.10 - When cyclodecane-1,6-dione is treated with sodium...Ch. 22.11 - Prob. 22.32PCh. 22.11 - Prob. 22.33PCh. 22.12 - Prob. 22.34PCh. 22.12 - Prob. 22.35PCh. 22.12 - Prob. 22.36PCh. 22.12 - Prob. 22.37PCh. 22.12 - Show what esters would undergo Claisen...Ch. 22.13 - Prob. 22.39PCh. 22.13 - Prob. 22.40PCh. 22.14 - Prob. 22.41PCh. 22.14 - Prob. 22.42PCh. 22.14 - Show how crossed Claisen condensations could be...Ch. 22.14 - Prob. 22.44PCh. 22.14 - Prob. 22.45PCh. 22.15 - Prob. 22.46PCh. 22.16 - Prob. 22.47PCh. 22.16 - Prob. 22.48PCh. 22.17 - Prob. 22.49PCh. 22.17 - Prob. 22.50PCh. 22.17 - Prob. 22.51PCh. 22.18 - Prob. 22.52PCh. 22.18 - Prob. 22.53PCh. 22.18 - Prob. 22.54PCh. 22.18 - Prob. 22.55PCh. 22.18 - Prob. 22.56PCh. 22.19 - Prob. 22.57PCh. 22.19 - Prob. 22.58PCh. 22.19 - Prob. 22.59PCh. 22 - Prob. 22.60SPCh. 22 - 1. Rank the following compounds in order of...Ch. 22 - Prob. 22.62SPCh. 22 - Prob. 22.63SPCh. 22 - Prob. 22.64SPCh. 22 - Pentane-2,4-dione (acetylacetone) exists as a...Ch. 22 - a. Rank these compounds in order of increasing...Ch. 22 - Prob. 22.67SPCh. 22 - Prob. 22.68SPCh. 22 - 22-69 Predict the products of the following...Ch. 22 - Predict the products of these reaction sequences.Ch. 22 - Show how you would accomplish the following...Ch. 22 - Prob. 22.72SPCh. 22 - Prob. 22.73SPCh. 22 - Prob. 22.74SPCh. 22 - The Knoevenagel condensation is a special case of...Ch. 22 - Prob. 22.76SPCh. 22 - Propose mechanisms for the following reactions.Ch. 22 - Prob. 22.78SPCh. 22 - Show how you would accomplish the following...Ch. 22 - Prob. 22.80SPCh. 22 - Propose a mechanism for the following reaction....Ch. 22 - Prob. 22.83SPCh. 22 - Prob. 22.84SPCh. 22 - Prob. 22.85SP
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
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
Living By Chemistry: First Edition Textbook
Chemistry
ISBN:9781559539418
Author:Angelica Stacy
Publisher:MAC HIGHER
Text book image
Organic And Biological Chemistry
Chemistry
ISBN:9781305081079
Author:STOKER, H. Stephen (howard Stephen)
Publisher:Cengage Learning,
Text book image
General, Organic, and Biological Chemistry
Chemistry
ISBN:9781285853918
Author:H. Stephen Stoker
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
Text book image
World of Chemistry, 3rd edition
Chemistry
ISBN:9781133109655
Author:Steven S. Zumdahl, Susan L. Zumdahl, Donald J. DeCoste
Publisher:Brooks / Cole / Cengage Learning