×
Log in to StudySoup
Get Full Access to Chemistry - Textbook Survival Guide
Join StudySoup for FREE
Get Full Access to Chemistry - Textbook Survival Guide

(a) Simple aminoacetals hydrolyze quickly and easily in

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 68SP Chapter 18

Organic Chemistry | 8th Edition

  • Textbook Solutions
  • 2901 Step-by-step solutions solved by professors and subject experts
  • Get 24/7 help from StudySoup virtual teaching assistants
Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

4 5 1 404 Reviews
20
3
Problem 68SP

(a) Simple aminoacetals hydrolyze quickly and easily in dilute acid. Propose a mechanism for hydrolysis of the following aminoacetal:

(b) The nucleosides that make up DNA have heterocyclic rings linked to deoxyribose by an aminoacetal functional group. Point out the aminoacetal linkages in deoxycytidine and deoxyadenosine.

(c) The stability of our genetic code depends on the stability of DNA. We are fortunate that the aminoacetal linkages of DNA are not easily cleaved. Show why your mechanism for part (a) does not work so well with deoxycytidine and deoxyadenosine.

Step-by-Step Solution:
Step 1 of 3

Solution 68SP

The oxygen is protonated by hydronium ion to form oxonium ion. The ring opening is takes place by attack of nucleophile.

(b) Ketones and aldehyde react with water to form hydrates; they also react with alcohols to form acetals. In the nucleosides, the carbon is bonded to oxygen and nitrogen this carbon is known aminoacetal carbon and this linkage this aminoacetal linkage.

The aminoacetal linkages in deoxycytidine...

Step 2 of 3

Chapter 18, Problem 68SP is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

Unlock Textbook Solution

Enter your email below to unlock your verified solution to:

(a) Simple aminoacetals hydrolyze quickly and easily in

×
Log in to StudySoup
Get Full Access to Chemistry - Textbook Survival Guide
Join StudySoup for FREE
Get Full Access to Chemistry - Textbook Survival Guide
×
Reset your password