Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 11.3, Problem 11.4P

(a)

Interpretation Introduction

To determine: The structures of the principal product when the given alcohol reacts with the given reagents.

Interpretation: The structures of the principal product when the given alcohol reacts with the given reagents are to be stated.

Concept introduction: Sodium dichromate with sulphuric acid is used for the conversion of primary alcohol into carboxylic acid and secondary alcohol into ketone. PCC is used for the conversion of primary alcohol into aldehyde and secondary alcohol into ketone. DMP is a mild oxidising agent, used for the conversion of primary alcohol into aldehyde, and secondary alcohol into ketone. NaOCl-TEMPO is used for the conversion of primary alcohol into carboxylic acid, and secondary alcohol into ketone. It is not used for the conversion of tertiary alcohol and thus gives no reaction.

(b)

Interpretation Introduction

To determine: The structures of the principal product when the given alcohol reacts with the given reagents.

Interpretation: The structures of the principal product when the given alcohol reacts with the given reagents are to be stated.

Concept introduction: Sodium dichromate with sulphuric acid is used for the conversion of primary alcohol into carboxylic acid, and secondary alcohol into ketone. PCC is used for the conversion of primary alcohol into aldehyde and secondary alcohol into ketone. DMP is a mild oxidising agent, used for the conversion of primary alcohol into aldehyde and secondary alcohol into ketone. NaOCl-TEMPO is used for the conversion of primary alcohol into carboxylic acid and secondary alcohol into ketone. It is not used for the conversion of tertiary alcohol and thus gives no reaction.

(c)

Interpretation Introduction

To determine: The structures of the principal product when the given alcohol reacts with the given reagents.

Interpretation: The structures of the principal product when the given alcohol reacts with the given reagents are to be stated.

Concept introduction: Sodium dichromate with sulphuric acid is used for the conversion of primary alcohol into carboxylic acid and secondary alcohol into ketone. PCC is used for the conversion of primary alcohol into aldehyde and secondary alcohol into ketone. DMP is a mild oxidising agent, used for the conversion of primary alcohol into aldehyde and secondary alcohol into ketone. NaOCl-TEMPO is used for the conversion of primary alcohol into carboxylic acid and secondary alcohol into ketone. It is not used for the conversion of tertiary alcohol and thus gives no reaction.

(d)

Interpretation Introduction

To determine: The structures of the principal product when the given alcohol reacts with the given reagents.

Interpretation: The structures of the principal product when the given alcohol reacts with the given reagents are to be stated.

Concept introduction: Sodium dichromate with sulphuric acid is used for the conversion of primary alcohol into carboxylic acid and secondary alcohol into ketone. PCC is used for the conversion of primary alcohol into aldehyde and secondary alcohol into ketone. DMP is a mild oxidising agent, used for the conversion of primary alcohol into aldehyde and secondary alcohol into ketone. NaOCl-TEMPO is used for the conversion of primary alcohol into carboxylic acid and secondary alcohol into ketone. It is not used for the conversion alcohols which is secondary but there is already a tertiary alcohol and thus gives no reaction.

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Chapter 11 Solutions

Organic Chemistry (9th Edition)

Ch. 11.1 - Prob. 11.1PCh. 11.2C - Prob. 11.2PCh. 11.3 - Prob. 11.3PCh. 11.3 - Prob. 11.4PCh. 11.3 - Prob. 11.5PCh. 11.3 - Suggest the most appropriate method for each of...Ch. 11.4 - A chronic alcoholic requires a much larger dose of...Ch. 11.4 - Unlike ethylene glycol, propylene glycol...Ch. 11.5 - Predict the major products of the following...Ch. 11.5 - Show how you would convert propan-1-ol to the...
Ch. 11.6 - Predict the products of the following reactions....Ch. 11.7A - Propose a mechanism for the reaction of a....Ch. 11.7B - Prob. 11.13PCh. 11.7B - Show how you would use a simple chemical test to...Ch. 11.7C - Neopentyl alcohol, (CH3)3CCH2OH, reacts with...Ch. 11.7C - Prob. 11.16PCh. 11.7C - When cis-2-methylcyclohexanol reacts with the...Ch. 11.8 - Prob. 11.18PCh. 11.9 - Prob. 11.19PCh. 11.9 - Prob. 11.20PCh. 11.9 - Prob. 11.21PCh. 11.10A - Prob. 11.22PCh. 11.10A - Some alcohols undergo rearrangement or other...Ch. 11.10B - Prob. 11.24PCh. 11.10B - Explain why the acid-catalyzed condensation is a...Ch. 11.10B - Prob. 11.26PCh. 11.10B - When the following substituted cycloheptanol...Ch. 11.11A - Prob. 11.28PCh. 11.11A - Prob. 11.29PCh. 11.11B - Predict the products formed by periodic acid...Ch. 11.12 - Prob. 11.31PCh. 11.13A - Prob. 11.32PCh. 11.14 - Prob. 11.33PCh. 11.14 - a. Show how ethanol and cyclohexanol may be used...Ch. 11.14 - Prob. 11.35PCh. 11.14 - Phenols (pKa 10) are more acidic than other...Ch. 11.14 - To practice working through the early parts of a...Ch. 11.14 - Prob. 11.38PCh. 11 - Predict the major products of the following...Ch. 11 - Show how you would convert 2-methylcyclopentanol...Ch. 11 - In each case, show how you would synthesize the...Ch. 11 - Prob. 11.42SPCh. 11 - Prob. 11.43SPCh. 11 - Prob. 11.44SPCh. 11 - Both cis- and trans-2-methylcyclohexanol undergo...Ch. 11 - Prob. 11.46SPCh. 11 - Prob. 11.47SPCh. 11 - Show how you would make each compound, beginning...Ch. 11 - Predict the major products (including...Ch. 11 - Show how you would use simple chemical tests to...Ch. 11 - The compound shown below has three different types...Ch. 11 - Prob. 11.52SPCh. 11 - Prob. 11.53SPCh. 11 - Prob. 11.54SPCh. 11 - Prob. 11.55SPCh. 11 - Show how you would synthesize the following...Ch. 11 - Show how you would synthesize the following...Ch. 11 - The following pseudo-syntheses (guaranteed not to...Ch. 11 - Two unknowns, X and Y, both having the molecular...Ch. 11 - The Williamson ether synthesis involves the...Ch. 11 - Prob. 11.61SPCh. 11 - Prob. 11.62SPCh. 11 - Alcohols combine with ketones and aldehydes to...Ch. 11 - Prob. 11.64SPCh. 11 - Prob. 11.65SPCh. 11 - Prob. 11.66SP
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