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# (a) Under certain conditions, the reaction of 0.5 M ISBN: 9780321768414 33

## Solution for problem 13P Chapter 6

Organic Chemistry | 8th Edition

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Problem 13P

(a) Under certain conditions, the reaction of 0.5 M 1-bromobutane with 1.0 M sodium methoxide forms 1-methoxybutane at a rate of 0.05 mol/L per second. What would be the rate if 0.1 M 1-bromobutane and 2.0 M NaOCH3 were used?

(b) Consider the reaction of 1-bromobutane with a large excess of ammonia (NH3). Draw the reactants, the transition state, and the products. Note that the initial product is the salt of an amine (RNH3+Br-), which is deprotonated by the excess ammonia to give the amine.

(c) Show another SN2 reaction using a different combination of an alkoxide and an alkyl bromide that also produces1-methoxybutane.

Step-by-Step Solution:

Solution 13P:

Step 1(a):

This is  a SN2 (Second order Nucleophilic Substitution reaction)  type of reaction. Therefore, the rate of the reaction is

Rate = k [ NaOCH3] [CH3CH2CH2CH2Br] -----(1)

Step 2:

It is given that,

[ NaOCH3] = 1.0 M

[CH3CH2CH2CH2Br] = 0.5 M

Rate = 0.05 mol/L per second

Therefore, from equation (1) we have

K = rate/ [ NaOCH3] [CH3CH2CH2CH2Br] = 0.1 L mol-1 s1-

Step 3:

Rate =?

[ NaOCH3] = 2.0 M

[CH3CH2CH2CH2Br] = 0.1 M

Therefore, from equation (1) we have

Rate = k [ NaOCH3] [CH3CH2CH2CH2Br] -----(1)

= 0.1 L mol-1 s1- x 2.0 M x 0.1 M = 0.02 mol L-1 s-1

Therefore, the rate of the reaction where 0.1 M 1-bromobutane and 2.0 M NaOCH3 were used is 0.02 mol L-1 s-1

Step 4 of 5

Step 5 of 5

##### ISBN: 9780321768414

This full solution covers the following key subjects: bromobutane, reaction, amine, rate, ammonia. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. Since the solution to 13P from 6 chapter was answered, more than 813 students have viewed the full step-by-step answer. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. Organic Chemistry was written by and is associated to the ISBN: 9780321768414. The answer to “(a) Under certain conditions, the reaction of 0.5 M 1-bromobutane with 1.0 M sodium methoxide forms 1-methoxybutane at a rate of 0.05 mol/L per second. What would be the rate if 0.1 M 1-bromobutane and 2.0 M NaOCH3 were used?(b) Consider the reaction of 1-bromobutane with a large excess of ammonia (NH3). Draw the reactants, the transition state, and the products. Note that the initial product is the salt of an amine (RNH3+Br-), which is deprotonated by the excess ammonia to give the amine.(c) Show another SN2 reaction using a different combination of an alkoxide and an alkyl bromide that also produces1-methoxybutane.” is broken down into a number of easy to follow steps, and 102 words. The full step-by-step solution to problem: 13P from chapter: 6 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM.

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