Predict the products of the reactions of the following

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

Problem 2P Chapter 11

Organic Chemistry | 8th Edition

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

Organic Chemistry | 8th Edition

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11
5
Problem 2P

Predict the products of the reactions of the following compounds with chromic acid and also with PCC. (a) cyclohexanol

(b) 1-methylcyclohexanol

(c) cyclopentylmethanol

(d) cyclohexanone

(e) cyclohexane

(f) acetic acid, CH3COOH

(g) ethanol

(h) acetaldehyde, CH3CHO

Step-by-Step Solution:

Solution 2P:

Here, we are going to Predict the products of the reactions of the following compounds with chromic acid and also with PCC.

PCC is Pyridinium chlorochromate (PCC) having a complex of chromium trioxide with pyridine and HCl. It is an oxidant. PCC oxidizes most primary alcohols to aldehydes in excellent yields. PCC is soluble in nonpolar solvents such as dichloromethane which is an excellent solvent for most organic compounds. PCC can also serve as a mild reagent for oxidizing secondary alcohols to ketones.

Chromic acid, H2CrO4, is a strong acid and is a reagent for oxidizing alcohols to ketones and carboxylic acids.

(a) cyclohexanol

Step 1:

The conversion of cyclohexanol to cyclohexanone in presence of PCC and chromic acid is given below:

Step 2:

(b) 1-methylcyclohexanol

The conversion of 1-methylcyclohexanol in presence of PCC and chromic acid is given below:

No product is formed in in presence of PCC and chromic acid. This is because 1-methylcyclohexanol has no Hydrogen atom in the carbinol carbon atom.

Step 3:

(c) cyclopentylmethanol

The conversion of cyclopentylmethanol in presence of PCC and chromic acid is given below:

Step 4:

(d) cyclohexanone

No product is formed in in presence of PCC and chromic acid. This is because cyclohexanone has no Hydrogen atom in the carbinol carbon atom.

Step 5 of 8

Chapter 11, Problem 2P is Solved
Step 6 of 8

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

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