Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 17.SE, Problem 45AP
Interpretation Introduction

a)

Organic Chemistry, Chapter 17.SE, Problem 45AP , additional homework tip  1

Interpretation:

Starting with benzene and using other alcohols of six or fewer carbons as the organic reagents how 1-ethylcyclohexanol can be prepared is to be stated.

Concept introduction:

An alicyclic 30 alcohol is to be prepared from benzene. For this purpose benzene has to be converted into an alicyclic ketone and then treated with Grignard reagent. Benzene can be converted into phenol, first by halogenation followed by treatment with NaOH. Phenol can be converted into cyclohexanol by reducing with H2, Rh/C in ethanol. Cyclohexanol when oxidized with pyridiniumchlorochromate is converted in to the alicyclic ketone, cyclohexanone, required.

To state:

Starting with benzene and using other alcohols of six or fewer carbons as the organic reagents how to prepare 1-ethylcyclohexanol.

Interpretation Introduction

b)

Organic Chemistry, Chapter 17.SE, Problem 45AP , additional homework tip  2

Interpretation:

Starting with benzene and using other alcohols of six or fewer carbons as the organic reagents how 3-methylhexan-1-ol can be prepared is to be given.

Concept introduction:

A six carbon straight chain alcohol with a methyl group on C3 is to be prepared from benzene. By ozonolysis, the benzene ring is broken to get the open chain dialdehyde glyoxal. To one of the aldehydic group in glyoxal, an isopentyl group can be introduced by treating with a suitable Grignard reagent. Upon heating the alcohol will eliminate water to yield an unsaturated aldehyde. The unsaturated aldehyde can be reduced to a saturated aldehyde which on NaBH4 reduction will lead to the formation of the product required.

To give:

Starting with benzene and using other alcohols of six or fewer carbons as the organic reagents how to prepare 3-methylhexan-1-ol.

Interpretation Introduction

c)

Organic Chemistry, Chapter 17.SE, Problem 45AP , additional homework tip  3

Interpretation:

Starting with benzene and using other alcohols of six or fewer carbons as the organic reagents how 2-methyl-2-phenyl-2 butanol can be prepared is to be given.

Concept introduction:

An aromatic 30 alcohol is required. Friedal-Crafts acylation of benzene with suitable acyl halide will produce an alkylphenyl ketone. The ketone when treated with a Grignard reagent will yield the 30 alcohol required.

To give:

Starting with benzene and using other alcohols of six or fewer carbons as the organic reagents how to prepare .

Interpretation Introduction

d)

Organic Chemistry, Chapter 17.SE, Problem 45AP , additional homework tip  4

Interpretation:

Starting with benzene and using other alcohols of six or fewer carbons as the organic reagents how 5-methylhexan-3-ol can be prepared is to be given.

Concept introduction:

A six carbon straight chain aldehyde with a methyl group on C4 is to be prepared from benzene. By ozonolysis, the benzene ring is broken to get the open chain dialdehyde, maloaldehyde with three carbon atoms. To one of the aldehydic group in the dialdehyde, an isobutyl group can be introduced by treating with a suitable Grignard reagent to get an aldol. The aldehyde group in the aldol is reduced to an alkyl group to get the alcohol requireds.

To give:

Starting with benzene and using other alcohols of six or fewer carbons as the organic reagents how to prepare 3-methylhexan-1-ol.

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Chapter 17 Solutions

Organic Chemistry

Ch. 17.5 - Use the reaction of a Grignard reagent with a...Ch. 17.6 - How would you carry out the following...Ch. 17.6 - What products(s) would you expect from dehydration...Ch. 17.7 - What alcohols would give the following products on...Ch. 17.7 - What products would you expect from oxidation of...Ch. 17.8 - TMS ethers can be removed by treatment with...Ch. 17.9 - Show the mechanism for the reaction of...Ch. 17.11 - Prob. 18PCh. 17.11 - When the 1HNMR spectrum of an alcohol is run in...Ch. 17.SE - Give IUPAC names for the following compounds:Ch. 17.SE - Draw the structure of the carbonyl compound(s)...Ch. 17.SE - Prob. 22VCCh. 17.SE - Prob. 23VCCh. 17.SE - Name and assign R or S stereochemistry to the...Ch. 17.SE - Evidence for the intermediate carbocations in the...Ch. 17.SE - Acid-catalyzed dehydration of 2,...Ch. 17.SE - Prob. 27MPCh. 17.SE - Treatment of the following epoxide with aqueous...Ch. 17.SE - Prob. 29MPCh. 17.SE - Prob. 30MPCh. 17.SE - Identify the type of substitution mechanism (SN1,...Ch. 17.SE - The conversion of 3 alcohols into alkenes under...Ch. 17.SE - Prob. 33MPCh. 17.SE - The trimethylsilyl (TMS) protecting group is one...Ch. 17.SE - When the alcohol below is treated with POCI3 and...Ch. 17.SE - Phenols generally have lower pKa’s than...Ch. 17.SE - Give IUPAC names for the following compounds:Ch. 17.SE - Draw and name the eight isomeric alcohols with...Ch. 17.SE - Prob. 39APCh. 17.SE - Named bombykol, the sex pheromone secreted by the...Ch. 17.SE - Carvacrol is a naturally occurring substance...Ch. 17.SE - What Grignard reagent and what carbonyl compound...Ch. 17.SE - What carbonyl compounds would you reduce to...Ch. 17.SE - What carbonyl compounds might you start with to...Ch. 17.SE - Prob. 45APCh. 17.SE - What products would you obtain from reaction of...Ch. 17.SE - Prob. 47APCh. 17.SE - How would you prepare the following compounds from...Ch. 17.SE - Prob. 49APCh. 17.SE - What products would you expect to obtain from...Ch. 17.SE - Prob. 51APCh. 17.SE - Propose structures for alcohols that have the...Ch. 17.SE - Propose a structure consistent with the following...Ch. 17.SE - The 1HNMR spectrum shown is that of...Ch. 17.SE - A compound of unknown structure gave the following...Ch. 17.SE - Propose a structure for a compound C15H24O that...Ch. 17.SE - Prob. 57APCh. 17.SE - Prob. 58APCh. 17.SE - Rank the following substituted phenols in order of...Ch. 17.SE - Benzvl chloride can be converted into benzaldehvde...Ch. 17.SE - Prob. 61APCh. 17.SE - Prob. 62APCh. 17.SE - Prob. 63APCh. 17.SE - Prob. 64APCh. 17.SE - Prob. 65APCh. 17.SE - Prob. 66APCh. 17.SE - Dehydration of trans-2-methylcyclopentanol with...Ch. 17.SE - 2, 3-Dimethyl-2, 3-butanediol has the common name...Ch. 17.SE - As a rule, axial alcohols oxidize somewhat faster...Ch. 17.SE - Prob. 70APCh. 17.SE - A problem often encountered in the oxidation of...Ch. 17.SE - Identify the reagents a-f in the Following scheme:Ch. 17.SE - Prob. 73APCh. 17.SE - Prob. 74APCh. 17.SE - Compound A, C8H10O, has the IR and 1H NMR spectra...Ch. 17.SE - Prob. 76APCh. 17.SE - Prob. 77AP
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