ORGANIC CHEMISTRY-ETEXT REG ACCESS
ORGANIC CHEMISTRY-ETEXT REG ACCESS
12th Edition
ISBN: 9781119308362
Author: Solomons
Publisher: WILEY
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Chapter 16, Problem 48P
Interpretation Introduction

Interpretation:

The structure for the reactants involved in the formation of a given product by the Horner Wadsworth Emmons reaction are to be written.

Concept introduction:

Horner Wadsworth Emmons modification is a name reaction of carbonyl compounds in which they react with phosphonate carbanion to form (E) - alkene.

The first step of this reaction is the deprotonation of a phosphonate ion to form a phosphonate carbanion.

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CH3 Ph3P-CHCH3 H3C H3C Aldehydes and ketones are converted into alkenes by means of a direct nucleophilic addition called the Wittig reaction. In the reaction, a triphenylphosphorine ylide, also called a phosphorane, adds to an aldehyde/ketone to give a four-membered cyclic intermediate called an oxaphosphetane. The oxaphosphetane is not isolated but instead spontaneously decomposes to release triphenylphosphine oxide and an alkene. Ph3P-CHCH3 H3C The ylide is formed by reaction of triphenylphosphine, a good nucleophile, with a primary alkyl halide in an S 2 reaction, followed by deprotonation of the carbon with a strong base, such as butyllithium. The carbonyl carbon and the carbon originally bonded to the halogen become the two carbons with the double bond in the product alkene :0: CH3 Com The real value of the Wittig reaction lies in its ability to yield an alkene of predictable structure, as the C-C bond is precisely where the C=O bond was in the reactant and no isomers (other than…

Chapter 16 Solutions

ORGANIC CHEMISTRY-ETEXT REG ACCESS

Ch. 16 - Prob. 11PPCh. 16 - Practice Problem 16.12 What product would be...Ch. 16 - Prob. 13PPCh. 16 - Practice Problem 16.14 Dihydropyran reacts readily...Ch. 16 - Practice Problem 16.15 Show how you might use...Ch. 16 - Practice Problem 16.16 (a) Show how you might...Ch. 16 - Practice Problem 16.17 In addition to...Ch. 16 - Practice Problem 16.18 Triphenylphosphine can be...Ch. 16 - Prob. 19PPCh. 16 - PRACTICE PROBLEM 16.20 Give the structure of the...Ch. 16 - PRACTICE PROBLEM 16.21 What would be the major...Ch. 16 - Prob. 22PCh. 16 - 16.23 Write structural formulas for the products...Ch. 16 - Give structural formulas for the products formed...Ch. 16 - 16.25 What products would be obtained when...Ch. 16 - Predict the major organic product from each of the...Ch. 16 - 16.27 Predict the major product from each of the...Ch. 16 - 16.28 Predict the major product from each of the...Ch. 16 - Prob. 29PCh. 16 - 16.30 Write detailed mechanisms for each of the...Ch. 16 - Prob. 31PCh. 16 - Prob. 32PCh. 16 - Show how you would convert benzaldehyde into each...Ch. 16 - 16.34 Show how ethyl phenyl ketone could be...Ch. 16 - Show how benzaldehyde could be synthesized from...Ch. 16 - Give structures for compounds AE. Cyclohexanol...Ch. 16 - Prob. 37PCh. 16 - Prob. 38PCh. 16 - Prob. 39PCh. 16 - Prob. 40PCh. 16 - Prob. 41PCh. 16 - Prob. 42PCh. 16 - 16.43 The structure of the sex pheromone...Ch. 16 - Provide reagents that would accomplish each of the...Ch. 16 - Write a detailed mechanism for the following...Ch. 16 - Prob. 46PCh. 16 - Dutch elm disease is caused by a fungus...Ch. 16 - Prob. 48PCh. 16 - Compounds W and X are isomers; they have the...Ch. 16 - Compounds Y and Z are isomers with the molecular...Ch. 16 - Compound A (C9H18O) forms a phenylhydrazone, but...Ch. 16 - Compound B (C8H12O2) shows a strong carbonyl...Ch. 16 - Prob. 53PCh. 16 - Prob. 54PCh. 16 - Prob. 55PCh. 16 - (a) What would be the frequencies of the two...Ch. 16 - Prob. 57PCh. 16 - Prob. LGP
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