Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 17.4, Problem 8P
Interpretation Introduction

a)

Organic Chemistry, Chapter 17.4, Problem 8P , additional homework tip  1

Interpretation:

All possible compounds which give benzyl alcohol on reduction with LiAlH4 are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH4. Acids, esters and aldehydes yield a 10 alcohol upon reduction with LiAlH4, while ketones yield 20 alcohols. The reaction is carried out in ether solution as LiAlH4 reacts violently with water and explodes when heated above 120oC.

To give:

All possible compounds which give benzyl alcohol on reduction with LiAlH4.

Interpretation Introduction

b)

Organic Chemistry, Chapter 17.4, Problem 8P , additional homework tip  2

Interpretation:

All possible compounds which give 1-phenylethanol on reduction with LiAlH4 are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH4. Acids, esters and aldehydes yield a 10 alcohol upon reduction with LiAlH4, while ketones yield 20 alcohols. The reaction is carried out in ether solution as LiAlH4 reacts violently with water and explodes when heated above 120oC.

To give:

All possible compounds which give 1-phenylethanol on reduction with LiAlH4.

Interpretation Introduction

c)

Organic Chemistry, Chapter 17.4, Problem 8P , additional homework tip  3

Interpretation:

All possible compounds which give cyclohexanol on reduction with LiAlH4 are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH4. Acids, esters and aldehydes yield a 10 alcohol upon reduction with LiAlH4, while ketones yield 20 alcohols. The reaction is carried out in ether solution as LiAlH4 reacts violently with water and explodes when heated above 120oC.

To give:

All possible compounds which give cyclohexanol on reduction with LiAlH4.

Interpretation Introduction

d)

Organic Chemistry, Chapter 17.4, Problem 8P , additional homework tip  4

Interpretation:

All possible compounds which give isobutyl alcohol on reduction with LiAlH4 are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH4. Acids, esters and aldehydes yield a 10 alcohol upon reduction with LiAlH4, while ketones yield 20 alcohols. The reaction is carried out in ether solution as LiAlH4 reacts violently with water and explodes when heated above 120oC.

To give:

All possible compounds which give isobutyl alcohol on reduction with LiAlH4.

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What carbonyl compounds give the following alcohols on reduction with LiAlH4? Show all possibilities.
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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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