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Organic Chemistry | 2nd Edition | ISBN: 9781118454312 | Authors: David R. Klein
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The conjugate base of diethyl malonate can serve as a

Chapter 22, Problem 22.95

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QUESTION:

The conjugate base of diethyl malonate can serve as a nucleophile to attack a wide range of electrophiles. Identify the product that is formed when the conjugate base of diethyl malonate reacts with each of the following electrophiles followed by acid workup: Br (a) O (b) Cl O (c) O (d) I (e) (f) CN O O O (g) (h) NO2

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QUESTION:

The conjugate base of diethyl malonate can serve as a nucleophile to attack a wide range of electrophiles. Identify the product that is formed when the conjugate base of diethyl malonate reacts with each of the following electrophiles followed by acid workup: Br (a) O (b) Cl O (c) O (d) I (e) (f) CN O O O (g) (h) NO2

ANSWER:

Step 1 of 8

Formation of the conjugate base of diethyl malonate.

When a proton of diethyl malonate is abstracted by a base, then the diethyl malonate acquires a negative charge which is its conjugate base. The resulting conjugate base since holding a negative charge, hence acts a good nucleophile and thus attacks a wide range of compounds which are discussed above.

a)

Reaction with 1-bromopropane.

The product formed during the reaction with diethyl oxirane.

                 

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