×
Log in to StudySoup
Get Full Access to Organic Chemistry - 8 Edition - Chapter 22 - Problem 59p
Join StudySoup for FREE
Get Full Access to Organic Chemistry - 8 Edition - Chapter 22 - Problem 59p

Already have an account? Login here
×
Reset your password

Show how you would use Robinson annulations to synthesize

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

Solution for problem 59P Chapter 22

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 1 397 Reviews
20
2
Problem 59P

Problem 59P

Show how you would use Robinson annulations to synthesize the following compounds. Work backward, remembering that the cyclohexenone is the new ring and that the double bond of the cyclohexenone is formed by the aldol with dehydration. Take apart the double bond, then see what structures the Michael donor and acceptor must have.  

Step-by-Step Solution:

Solution:

Here we have to show the synthesis of the following compounds by Robinson annulations

  1.                                                  (b)

                                           

The Robinson Annulation reaction involves the formation of six-membered rings in polycyclic compounds, such as steroids. It combines two reactions: the Michael Addition and the Aldol Condensation reaction.

Step 1

Synthesis of 2-methyldicyclohex-2-enone

The 1st step involves generation of nucleophile, which will added with ketone (1-ethylprop-2-en) and forms 3-cyclohexanone-1-ethylpropane, which in presence of a base release one molecule of H2O and forms carbanion ion (intermediate), which undergoes rearrangement reaction involves breaking of C=O and formation of C-C followed by base catalysed reaction and forms 2-methyl-3-hydroxydicyclohexanone which on heating release one molecule of water and forms

 2-methyldicyclohex-2-enone as the product.

(cyclohexanone)                                   ( 3-cyclohexanone-1-ethylpropane)

 ( 3-cyclohexanone-1-ethylpropane)                              (Intermediate)

        (2-methyl-3-hydroxydicyclohexanone)    ( 2-methyldicyclohex-2-enone)

Step 2 of 1

Chapter 22, Problem 59P is Solved
Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

The full step-by-step solution to problem: 59P from chapter: 22 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. The answer to “Show how you would use Robinson annulations to synthesize the following compounds. Work backward, remembering that the cyclohexenone is the new ring and that the double bond of the cyclohexenone is formed by the aldol with dehydration. Take apart the double bond, then see what structures the Michael donor and acceptor must have.” is broken down into a number of easy to follow steps, and 53 words. This full solution covers the following key subjects: Bond, Double, cyclohexenone, michael, backward. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. Since the solution to 59P from 22 chapter was answered, more than 285 students have viewed the full step-by-step answer. Organic Chemistry was written by and is associated to the ISBN: 9780321768414.

Other solutions

People also purchased

Related chapters

Unlock Textbook Solution

Enter your email below to unlock your verified solution to:

Show how you would use Robinson annulations to synthesize