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Deuterium (D) is the isotope of hydrogen of mass number 2,

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 75SP Chapter 6

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 75SP

Deuterium (D) is the isotope of hydrogen of mass number 2, with a proton and a neutron in its nucleus. The chemistry of deuterium is nearly identical to the chemistry of hydrogen, except that the bond is slightly (5.0 kJ mol, or 1.2 kcal mol) stronger than the bond. Reaction rates tend to be slower if a bond (as opposed to a bond) is broken in a rate-limiting step. This effect on the rate is called a kinetic isotope effect. (Review Problem 4-56.)

(a) Propose a mechanism to explain each product in the following reaction.

(b) When the following deuterated compound reacts under the same conditions, the rate of formation of the substitution product is unchanged, while the rate of formation of the elimination product is slowed by a factor of 7.

Explain why the elimination rate is slower, but the substitution rate is unchanged.

(c) A similar reaction takes place on heating the alkyl halide in an acetone/water mixture.

Give a mechanism for the formation of each product under these conditions, and predict how the rate of formation of each product will change when the deuterated halide reacts. Explain your prediction.

Step-by-Step Solution:
Step 1 of 3

Step-1

(a) 

Mechanism of the above reaction is given below,

Step-2

(b)

In the E2 reaction, there is a breaking of  C-H bond, when D is substituted for H, this causes slowing the reaction. Whereas in in SN2 reaction there is no bond breaking of C-H bond, hence the rate of the reaction remains unchanged.

Step-3

(c)

Step 2 of 3

Chapter 6, Problem 75SP is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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Deuterium (D) is the isotope of hydrogen of mass number 2,

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