EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 9780100591318
Author: McMurry
Publisher: YUZU
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Chapter 17.5, Problem 10P
Interpretation Introduction

a) 2-Methyl-2-propanol

Interpretation:

A method to prepare 2-methyl-2-propanol using a Grignard reagent is to be given.

Concept introduction:

Grignard reagents react with formaldehyde to produce 10 alcohols, with other aldehydes to yield 20 alcohols and with ketones to give 30 alcohols as the product. Esters also when treated with two molar equivalents of Grignard reagents yield 30 alcohols.

To give:

A method to prepare 2-methyl-2-propanol using a Grignard reagent.

Interpretation Introduction

b) 1-Methylcyclohexanol

Interpretation:

A method to prepare 1-methylcyclohexanol using a Grignard reagent is to be given.

Concept introduction:

Grignard reagents react with formaldehyde to produce 10 alcohols, with other aldehydes to yield 20 alcohols and with ketones to give 30 alcohols as the product. Esters also when treated with two molar equivalents of Grignard reagents yield 30 alcohols.

To give:

A method to prepare 1-methylcyclohexanol using a Grignard reagent.

Interpretation Introduction

c) 3-Methyl-3-pentanol

Interpretation:

A method to prepare 3-methyl-3 pentanol using a Grignard reagent is to be given.

Concept introduction:

Grignard reagents react with formaldehyde to produce 10 alcohols, with other aldehydes to yield 20 alcohols and with ketones to give 30 alcohols as the product. Esters also when treated with two molar equivalents of Grignard reagents yield 30 alcohols.

To give:

A method to prepare 3-methyl-3-pentanol using a Grignard reagent.

Interpretation Introduction

d) 2-Phenyl-2-butanol

Interpretation:

A method to prepare 2-phenyl-2-butanol using a Grignard reagent is to be given.

Concept introduction:

Grignard reagents react with formaldehyde to produce 10 alcohols, with other aldehydes to yield 20 alcohols and with ketones to give 30 alcohols as the product

To give:

A method to prepare 2-phenyl-2-butanol using a Grignard reagent.

Interpretation Introduction

e) Benzyl alcohol

Interpretation:

A method to prepare benzyl alcohol using a Grignard reagent is to be given.

Concept introduction:

Grignard reagents react with formaldehyde to produce 10 alcohols, with other aldehydes to yield 20 alcohols and with ketones to give 30 alcohols as the product. Esters also when treated with two molar equivalents of Grignard reagents yield 30 alcohols.

To give:

A method to prepare benzyl alcohol using a Grignard reagent.

Interpretation Introduction

f) 4-Methyl-1-pentanol

Interpretation:

A method to prepare 4-methyl-1-pentanol using a Grignard reagent is to be given.

Concept introduction:

Grignard reagents react with formaldehyde to produce 10 alcohols, with other aldehydes to yield 20 alcohols and with ketones to give 30 alcohols as the product. Esters also when treated with two molar equivalents of Grignard reagents yield 30 alcohols.

To give:

A method to prepare 4-methyl-1-pentanol using a Grignard reagent.

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Chapter 17 Solutions

EBK 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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