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Chapter 8: Q.62 (page 330)

Explain why the reaction of 2-bromopropane withNaOCOCH3 gives(CH3)2CHOCOCH3 exclusively as product, but the reaction of 2-bromopropane with NaOCH2CH3gives a mixture of (CH3)2CHOCH2CH3(20%) and CH3CH=CH2(80%).

Short Answer

Expert verified

The reason is acetate ion is a powerful nucleophile than a base and only promotes substitution product. But ethoxides act both as a strong base and a strong nucleophile.

Step by step solution

01

Function of ethoxide

Ethoxide is a strong base as well as a strong nucleophile. Hence they give both an elimination and a substitution product.

02

Function of acetate anion

Acetate anion acts only as a good nucleophile. Hence, they exclusively give a substitution product.

Keeping into account all the key points, the products with their mode of reaction are shown below:-

Representation of the substituted and eliminated products

The difference in the concentration is observed here because acetate ion is a powerful nucleophile than a base and only promotes substitution product. In contrast, ethoxides act both as a strong base and a strong nucleophile. Hence, they promote both substitution and elimination products.

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Most popular questions from this chapter

Rank the following alkenes in order of increasing stability:

What is the major E2 elimination product formed from each halide?

a.

b.

c.

For which reaction mechanisms鈥�SN1,SN2,E1, or E2鈥攁re each of the following statements true? A statement may be true for one or more mechanisms.

a. The mechanism involves carbocation intermediates.

b. The mechanism has two steps.

c. The reaction rate increases with better leaving groups.

d. The reaction rate increases when the solvent is changed from CH3OHto localid="1648646954099" (CH3)2SO.

e. The reaction rate depends on the concentration of the alkyl halide only.

f. The mechanism is concerted.

g. The reaction of localid="1648646960420" CH3CH2Brwith NaOH occurs by this mechanism.

h. Racemization at a stereogenic center occurs.

i. Tertiary (3掳) alkyl halides react faster than 2掳 or 1掳 alkyl halides.

j. The reaction follows a second-order rate equation.

What alkyl halide forms each of the following alkenes as the onlyproduct in an elimination reaction?

a.

b.

c.

d.

Draw the major E2 elimination products from each of the following alkyl halides.

a.

b.
See all solutions

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