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Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485

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BuyFindarrow_forward

Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485
Chapter 11.6, Problem 14P
Textbook Problem
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Review the mechanism of geraniol biosynthesis shown in Figure 11-15, and propose a mechanism for the biosynthesis of limonene from linalyl diphosphate.

Chapter 11.6, Problem 14P, Review the mechanism of geraniol biosynthesis shown in Figure 11-15, and propose a mechanism for the

Interpretation Introduction

Interpretation:

The mechanism for the biosynthesis of limonene from linalyl diphosphate is interpreted.

Concept introduction:

In biological synthesis both SN1 and SN2 mechanisms occurs. In biosynthesis the substrate contains organodiphosphate group rather than alkyl halide geroup. So the leaving group will be diphosphate ion. Diphosphate ion is a better leaving group like halide ion.

Explanation of Solution

Initially SN1 reaction occurs and a carbocation formed in first step...

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Chapter 11 Solutions

Organic Chemistry
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Ch. 11.5 - Rank the following substances in order of their...Ch. 11.5 - 3-Bromo-1-butene and 1-bromo-2-butene undergo SN1...Ch. 11.5 - Predict whether each of the following substitution...Ch. 11.6 - Review the mechanism of geraniol biosynthesis...Ch. 11.7 - Ignoring double-bond stereochemistry, what...Ch. 11.7 - What alkyl halides might the following alkenes...Ch. 11.8 - What stereochemistry do you expect for the alkene...Ch. 11.8 - What stereochemistry do you expect for the...Ch. 11.9 - Which isomer would you expect to undergo E2...Ch. 11.12 - Tell whether each of the following reactions is...Ch. 11.SE - Write the product you would expect from reaction...Ch. 11.SE - From what alkyl bromide was the following alkyl...Ch. 11.SE - Assign R or S configuration to the following...Ch. 11.SE - Draw the structure and assign Z or E...Ch. 11.SE - Predict the product(s) and show the mechanism for...Ch. 11.SE - Show the mechanism for each reaction below. What...Ch. 11.SE - Predict the product(s) for each elimination...Ch. 11.SE - Predict the product(s) for each elimination...Ch. 11.SE - Predict the product(s) for each elimination...Ch. 11.SE - Predict the product of each reaction below and...Ch. 11.SE - We saw in Section 8-7 that bromohydrins are...Ch. 11.SE - The following tertiary alkyl bromide does not...Ch. 11.SE - Metabolism of S-adenosylhomocysteine (Section...Ch. 11.SE - Reaction of iodoethane with CN- yields a small...Ch. 11.SE - One step in the urea cycle for ridding the body of...Ch. 11.SE - Methyl esters (RCO2CH3) undergo a cleavage...Ch. 11.SE - SN2 reactions take place with inversion of...Ch. 11.SE - Propose a mechanism for the following reaction, an...Ch. 11.SE - Draw all isomers of C4H9Br, name them, and arrange...Ch. 11.SE - The following Walden cycle has been carried out....Ch. 11.SE - Which compound in each of the following pairs will...Ch. 11.SE - Which reactant in each of the following pairs is...Ch. 11.SE - What effect would you expect the following changes...Ch. 11.SE - What effect would you expect the following changes...Ch. 11.SE - How might you prepare each of the following...Ch. 11.SE - Which reaction in each of the following pairs...Ch. 11.SE - Predict the product and give the stereochemistry...Ch. 11.SE - (R)-2-Bromooctane undergoes racemization to give...Ch. 11.SE - Propose structures for compounds that fit the...Ch. 11.SE - What products would you expect from the reaction...Ch. 11.SE - 1-Chloro-1, 2-diphenylethane can undergo E2...Ch. 11.SE - Predict the major alkene product of the following...Ch. 11.SE - There are eight diastereomers of 1, 2, 3, 4, 5,...Ch. 11.SE - The reactions shown below are unlikely to occur as...Ch. 11.SE - Arrange the carbocations below, in order of...Ch. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Predict the major product(s) of each reaction...Ch. 11.SE - Reaction of the following S tosylate with cyanide...Ch. 11.SE - Ethers can often be prepared by SN2 reaction of...Ch. 11.SE - Show the stereochemistry of the epoxide (see...Ch. 11.SE - In light of your answer to Problem 11-31, what...Ch. 11.SE - In addition to not undergoing substitution...Ch. 11.SE - The tosylate of (2R, 3S)-3-phenyl-2-butanol...Ch. 11.SE - In light of your answer to Problem 11-64, which...Ch. 11.SE - How can you explain the fact that...Ch. 11.SE - Predict the product(s) of the following reaction,...Ch. 11.SE - Alkynes can be made by dehydrohalogenation of...Ch. 11.SE - Based on your answer to Problem 11-68, predict the...Ch. 11.SE - (S)-2-Butanol slowly racemizes on standing in...Ch. 11.SE - Reaction of HBr with (R)-3-methyl-3-hexanol leads...Ch. 11.SE - Treatment of 1-bromo-2-deuterio-2-phenylethane...Ch. 11.SE - Propose a structure for an alkyl halide that gives...Ch. 11.SE - Although anti periplanar geometry is preferred for...Ch. 11.SE - In light of your answer to Problem 11-74, explain...Ch. 11.SE - The reaction of 1-chlorooctane with CH3CO2- to...Ch. 11.SE - Compound X is optically inactive and has the...Ch. 11.SE - When a primary alcohol is treated with...Ch. 11.SE - The amino acid methionine is formed by a...Ch. 11.SE - Amines are converted into alkenes by a two-step...Ch. 11.SE - The antipsychotic drug flupentixol is prepared by...

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