When the following compound is treated with sodium

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

Problem 76SP 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 76SP

When the following compound is treated with sodium methoxide in methanol, two elimination products are possible. Explain why the deuterated product predominates by about a 7:1 ratio (refer to Problem 6-75).

Reference: Exercise 76:

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

Here mechanism of the reaction involves E2 reaction. It is known that the C-D cleavage can be up to 7 times slower than C-H cleavage, so the formed from the breaking of C-H should be 7 times fast and the ratio is  7:1.

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Step 2 of 3

Chapter 6, Problem 76SP is Solved
Step 3 of 3

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

The answer to “When the following compound is treated with sodium methoxide in methanol, two elimination products are possible. Explain why the deuterated product predominates by about a 7:1 ratio (refer to 6-75). Reference: Exercise 76: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 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.” is broken down into a number of easy to follow steps, and 221 words. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. Organic Chemistry was written by Sieva Kozinsky and is associated to the ISBN: 9780321768414. The full step-by-step solution to problem: 76SP from chapter: 6 was answered by Sieva Kozinsky, our top Chemistry solution expert on 05/06/17, 06:41PM. Since the solution to 76SP from 6 chapter was answered, more than 342 students have viewed the full step-by-step answer. This full solution covers the following key subjects: rate, Product, Bond, explain, Formation. This expansive textbook survival guide covers 25 chapters, and 1336 solutions.

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