×
Log in to StudySoup
Get Full Access to Organic Chemistry - 8 Edition - Chapter 18 - Problem 48sp
Join StudySoup for FREE
Get Full Access to Organic Chemistry - 8 Edition - Chapter 18 - Problem 48sp

Already have an account? Login here
×
Reset your password

The following road-map problem centers on the structure

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

Solution for problem 48SP 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 1 244 Reviews
26
0
Problem 48SP

The following road-map problem centers on the structure and properties of A, a key intermediate in these reactions. Give structures for compounds A through J.

Step-by-Step Solution:
Step 1 of 3

Solution 48SP

Aldehydes undergo oxidation in presence of PCC to form carbonyl compounds.

Primary alcohols react with PCC to form aldehydes and the secondary alcohols react with PCC to form ketones.

The reaction is as follows:

Aldehydes form acetals more readily than ketones. So, selectively protect the aldehyde as a acetal by reacting with 1,2-diol.

2-oxo cyclohexanecarbaldehyde reacts with ethane 1,2-diol to form the product A.

The reaction is as follows:

Ketones react with phenylhydrazine to form phenylhydrazone and followed by acidic hydrolysis of acetal in presence of to give the deprotected aldehyde.

The reaction is as follows:

Only aldehydes react with Tollen’s reagent to form silver mirror. Ketones cannot react with tollen’s reagent.

The reaction is as follows:

Here, aldehyde is protected as an acetal and ketone cannot react with tollen’s reagent, so, No reaction occur.

Acetal reacts with dilute chromic acid to form 2-oxo cyclohexanecarbaldehyde.

The 2-oxo cyclohexanecarbaldehyde undergoes clemmensen reduction in presence of to form the product F (methylcyclohexane).

The reaction is as follows:

Ketone reacts with methylmagnesium iodide (Grignard reagent) and followed by hydrolysis to form the product G.

The reaction is as follows:

Aldehydes undergo reduction in presence of Na to form alcohols.

The reaction is as follows:

The reactant G undergoes dehydration in presence of an acid to form the product I.

The reaction is as follows:

Aldehydes react with Grignard reagent (cyclopentyl magnesium bromide) and followed by hydrolysis () to form alcohols.

The reaction is as follows:

Step 2 of 3

Chapter 18, Problem 48SP is Solved
Step 3 of 3

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

This full solution covers the following key subjects: Centers, compounds, give, Intermediate, key. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. Organic Chemistry was written by and is associated to the ISBN: 9780321768414. The full step-by-step solution to problem: 48SP from chapter: 18 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. The answer to “The following road-map problem centers on the structure and properties of A, a key intermediate in these reactions. Give structures for compounds A through J.” is broken down into a number of easy to follow steps, and 25 words. Since the solution to 48SP from 18 chapter was answered, more than 1762 students have viewed the full step-by-step answer. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8.

Other solutions

People also purchased

Related chapters

Unlock Textbook Solution

Enter your email below to unlock your verified solution to:

The following road-map problem centers on the structure