Organic Chemistry - With Access (Custom)
Organic Chemistry - With Access (Custom)
9th Edition
ISBN: 9781337031745
Author: McMurry
Publisher: Cengage
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Chapter 17.SE, Problem 49AP
Interpretation Introduction

a) Cyclopentanone

Interpretation:

How to prepare cyclopentanone from cyclopentanol is to be stated.

Concept introduction:

Ketones can be prepared by oxidizing 20 alcohols with acidified CrO3.

To state:

How to prepare cyclopentanone from cyclopentanol.

Interpretation Introduction

b) Cyclopentene

Interpretation:

How to prepare cyclopentene from cyclopentanol is to be stated.

Concept introduction:

Alcohols can be converted into alkenes by treating them with POCl3 in pyridine.

To state:

How to prepare cyclopentene from cyclopentanol.

Interpretation Introduction

c) 1-Methylcyclopentanol

Interpretation:

How to prepare1-methylcyclopentanol from cyclopentanol is to be stated.

Concept introduction:

A 20 alcohol is to be converted into a 30 alcohol. Oxidizing the alcohol to a ketone and treating the ketone with a Grignard reagent will lead to the formation of the 30 alcohol.

To state:

How to prepare 1-methylcyclopentanol from cyclopentanol is to be stated.

Interpretation Introduction

d) trans-2-Methylcyclopentanol

Interpretation:

How to prepare trans-2-Methylcyclopentanol from cyclopentanol is to be stated.

Concept introduction:

Alcohols when treated with acids undergo dehydration to yield an alkene. The alkenes can be hydrated either by oxymercuration-demercuration process following Markovnikov regiochemistry or by hydroboration-oxidation following anti-Markovnikov regiochemistry.

To state:

How to prepare trans-2-methylcyclopentanol from cyclopentanol.

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Chapter 17 Solutions

Organic Chemistry - With Access (Custom)

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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