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Predict the products of the reactions of the following

Chapter 3, Problem 2P

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QUESTION:

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

Questions & Answers

QUESTION:

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

ANSWER:

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:

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