ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
9th Edition
ISBN: 9780134645704
Author: WADE AND SIMEK
Publisher: PEARSON
Question
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Chapter 11.14, Problem 11.38P

(a)

Interpretation Introduction

Interpretation:

The synthesis of given compound with the use of cyclopentanol, alcohols that have no more than four carbon atoms as starting materials and any common reagents and solvents is to be stated.

Concept introduction:

The sulphuric acid catalyzed dehydration reaction is used to convert alcohols into respective alkenes. The reaction of an alkene with m-CPBA followed by hydrolysis leads to the formation of diol with inversion of configuration.

(b)

Interpretation Introduction

Interpretation:

The synthesis of given compound with the use of cyclopentanol, alcohols that have no more than four carbon atoms as starting materials and any common reagents and solvents is to be stated.

Concept introduction:

The reaction of secondary alcohols with PCC leads to the formation of ketone. The Wittig reaction of ketone through phosphorous ylides leads to the addition of double bond (alkene). The reaction of an alkene with halogen acids leads to the addition of halogen group.

(c)

Interpretation Introduction

Interpretation:

The synthesis of given compound with the use of cyclopentanol, alcohols that have no more than four carbon atoms as starting materials and any common reagents and solvents is to be stated.

Concept introduction:

The reaction of secondary alcohols with PCC leads to the formation of ketone. The Wittig reaction of ketone through phosphorous ylides leads to the addition of double bond (alkene). The reaction of an alkene with m-CPBA in the presence of DCM leads to the formation of epoxide.

(d)

Interpretation Introduction

Interpretation:

The synthesis of given compound with the use of cyclopentanol, alcohols that have no more than four carbon atoms as starting materials and any common reagents and solvents is to be stated.

Concept introduction:

The reaction of secondary alcohols with PCC leads to the formation of ketone.

The conversion of an alcohol into an alkyl bromide is done by PBr3. The formation of Grignard reagent is done by reaction of an alkyl halide with Mg/THF.

The reaction of Grignard reagent with ketone yields an alcohol. The reaction of an alcohol with TsCl/Pyridine leads to the addition of tosyl group (tosylate ester). The reaction of tosylate ester with sodium methoxide yields ether.

(e)

Interpretation Introduction

Interpretation:

The synthesis of given compound with the use of cyclopentanol, alcohols that have no more than four carbon atoms as starting materials and any common reagents and solvents is to be stated.

Concept introduction:

The conversion of an alcohol into an alkyl bromide is done by PBr3. The conversion of bromine into cyano group is done by NaCNorCuCN/Pyridine. The hydrolysis (acidic or basic of) cyano group leads to the formation of carboxylic acid. The conversion of carboxylic acid into acyl chloride is done by SOCl2orPCl3. The reduction of acyl chloride into R-CH2-OH is done by LiAlH4/ether followed by hydrolysis. The reaction of primary alcohols with PCC leads to the formation of an aldehyde. The reaction of Grignard reagent with an aldehyde yields an alcohol.

The reaction of an alcohol with TsCl/Pyridine leads to the addition of tosyl group (tosylate ester). The reaction of tosylate ester with sodium ethoxide yields ether.

(f)

Interpretation Introduction

Interpretation:

The synthesis of given compound with the use of cyclopentanol, alcohols that have no more than four carbon atoms as starting materials and any common reagents and solvents is to be stated.

Concept introduction:

The reaction of secondary alcohols with PCC leads to the formation of ketone. The conversion of an alcohol into an alkyl iodide is done by HI. The conversion of alkyl halide into alkyl nitrile is done by KCN. The conversion of bromine into cyano group is done by KCN. The hydrolysis (acidic or basic ) of cyano group leads to the formation of carboxylic acid. The conversion of carboxylic acid into acyl chloride is done by SOCl2orPCl3. The reduction of acyl chloride into R-CH2-OH is done by LiAlH4/ether followed by hydrolysis. The reaction of primary alcohols with PCC leads to the formation of an aldehyde. The reaction of Grignard reagent with an aldehyde yields an alcohol. The conversion of an alcohol into an alkyl bromide is done by PBr3. The reaction of an alcohol with TsCl/Pyridine leads to the addition of tosyl group (tosylate ester). The reaction of tosylate ester with sodium methoxide yields ether.

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Chapter 11 Solutions

ORGANIC CHEMISTRY

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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