EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
2nd Edition
ISBN: 9780393543971
Author: KARTY
Publisher: VST
Question
Book Icon
Chapter 20, Problem 20.31P
Interpretation Introduction

(a)

Interpretation:

The major organic product of the given reaction is to be predicted, and the mechanism for the given reaction is to be drawn.

Concept introduction:

In a transesterification reaction, one ester is converted into another. The mechanism for the transesterification reaction involves a nucleophile and a carboxylic acid derivative. This reaction is known as a nucleophilic addition-elimination reaction, which takes place in two steps. In the first step, the nucleophile adds to the electron-poor carbon in the carboxylic acid derivative. A tetrahedral intermediate is created. In the next step, the C=O bond is regenerated, and the leaving group (alkoxide ion) leaves. Overall, nucleophilic elimination results in substitution at the carbonyl carbon that is part of an acyl group. Cyclic esters tend to undergo ring-opening transesterification reactions.

Interpretation Introduction

(b)

Interpretation:

The major organic product of the given reaction is to be predicted, and the mechanism for the given reaction is to be drawn.

Concept introduction:

In a saponification reaction, an ester reacts with HO to produce an initial carboxylic acid that is rapidly and irreversibly deprotonated under the basic conditions. This is an example of a nucleophilic addition-elimination reaction. In the first step, the nucleophile adds to the electron-poor carbon in the carboxylic acid derivative. A tetrahedral intermediate is created. In the next step, the C=O bond is regenerated, and the leaving group (alkoxide ion) leaves. Two back to back proton transfer reactions take place to yield an original carboxylic acid.

Blurred answer
Students have asked these similar questions
Y= - 0.039 (14.01) + 0.7949
Suppose 1.76 g of magnesium acetate (Mg (CH3CO2)2) are dissolved in 140. mL of water. Find the composition of the resulting electrolyte solution. In particular, list the chemical symbols (including any charge) of each dissolved ion in the table below. List only one ion per row. mEq Then, calculate the concentration of each ion in dwrite the concentration in the second column of each row. Be sure you round your answers to the L correct number of significant digits. ion Add Row mEq L x 5
A pdf file of your hand drawn, stepwise mechanisms for the reactions. For each reaction in the assignment, you must write each mechanism three times (there are 10 reactions, so 30 mechanisms). (A) do the work on a tablet and save as a pdf., it is expected to write each mechanism out and NOT copy and paste the mechanism after writing it just once. Everything should be drawn out stepwise  and  every bond that is formed and broken in the process of the reaction, and is expected to see all relevant lone pair electrons and curved arrows.

Chapter 20 Solutions

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M

Ch. 20 - Prob. 20.11PCh. 20 - Prob. 20.12PCh. 20 - Prob. 20.13PCh. 20 - Prob. 20.14PCh. 20 - Prob. 20.15PCh. 20 - Prob. 20.16PCh. 20 - Prob. 20.17PCh. 20 - Prob. 20.18PCh. 20 - Prob. 20.19PCh. 20 - Prob. 20.20PCh. 20 - Prob. 20.21PCh. 20 - Prob. 20.22PCh. 20 - Prob. 20.23PCh. 20 - Prob. 20.24PCh. 20 - Prob. 20.25PCh. 20 - Prob. 20.26PCh. 20 - Prob. 20.27PCh. 20 - Prob. 20.28PCh. 20 - Prob. 20.29PCh. 20 - Prob. 20.30PCh. 20 - Prob. 20.31PCh. 20 - Prob. 20.32PCh. 20 - Prob. 20.33PCh. 20 - Prob. 20.34PCh. 20 - Prob. 20.35PCh. 20 - Prob. 20.36PCh. 20 - Prob. 20.37PCh. 20 - Prob. 20.38PCh. 20 - Prob. 20.39PCh. 20 - Prob. 20.40PCh. 20 - Prob. 20.41PCh. 20 - Prob. 20.42PCh. 20 - Prob. 20.43PCh. 20 - Prob. 20.44PCh. 20 - Prob. 20.45PCh. 20 - Prob. 20.46PCh. 20 - Prob. 20.47PCh. 20 - Prob. 20.48PCh. 20 - Prob. 20.49PCh. 20 - Prob. 20.50PCh. 20 - Prob. 20.51PCh. 20 - Prob. 20.52PCh. 20 - Prob. 20.53PCh. 20 - Prob. 20.54PCh. 20 - Prob. 20.55PCh. 20 - Prob. 20.56PCh. 20 - Prob. 20.57PCh. 20 - Prob. 20.58PCh. 20 - Prob. 20.59PCh. 20 - Prob. 20.60PCh. 20 - Prob. 20.61PCh. 20 - Prob. 20.62PCh. 20 - Prob. 20.63PCh. 20 - Prob. 20.64PCh. 20 - Prob. 20.65PCh. 20 - Prob. 20.66PCh. 20 - Prob. 20.67PCh. 20 - Prob. 20.68PCh. 20 - Prob. 20.69PCh. 20 - Prob. 20.70PCh. 20 - Prob. 20.71PCh. 20 - Prob. 20.1YTCh. 20 - Prob. 20.2YTCh. 20 - Prob. 20.3YTCh. 20 - Prob. 20.4YTCh. 20 - Prob. 20.5YTCh. 20 - Prob. 20.6YTCh. 20 - Prob. 20.7YTCh. 20 - Prob. 20.8YTCh. 20 - Prob. 20.9YTCh. 20 - Prob. 20.10YTCh. 20 - Prob. 20.11YTCh. 20 - Prob. 20.12YTCh. 20 - Prob. 20.13YT
Knowledge Booster
Background pattern image
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY