The structure of major organic product and pathway followed that would result from reaction of 1-bromopropane with sodium cyanide in acetone should be written. Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene . Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 . Analogous to the case that strong nucleophiles are more favored to react via S N 2 pathway, greater concentration of strong bases are more favored for single-step elimination E 2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E 2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

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Answer 1

Question

Chapter 7.9, Problem 7.18E

(a)

Interpretation Introduction

Interpretation: The structure of major organic product and pathway followed that would result from reaction of 1-bromopropane with sodium cyanide in acetone should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

(b)

Interpretation Introduction

Interpretation: The structure of major organic product that would result from reaction of 1-bromopropane with sodium methoxide in methanol should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

(c)

Interpretation Introduction

Interpretation: The structure of major organic product that would result from reaction of 1-bromopropane with potassium tert-butoxide tert-butanol should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

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Answer 2

Question

Chapter 7.9, Problem 7.18E

(a)

Interpretation Introduction

Interpretation: The structure of major organic product and pathway followed that would result from reaction of 1-bromopropane with sodium cyanide in acetone should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

(b)

Interpretation Introduction

Interpretation: The structure of major organic product that would result from reaction of 1-bromopropane with sodium methoxide in methanol should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

(c)

Interpretation Introduction

Interpretation: The structure of major organic product that would result from reaction of 1-bromopropane with potassium tert-butoxide tert-butanol should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

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Answer 3

Question

Chapter 7.9, Problem 7.18E

(a)

Interpretation Introduction

Interpretation: The structure of major organic product and pathway followed that would result from reaction of 1-bromopropane with sodium cyanide in acetone should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

(b)

Interpretation Introduction

Interpretation: The structure of major organic product that would result from reaction of 1-bromopropane with sodium methoxide in methanol should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

(c)

Interpretation Introduction

Interpretation: The structure of major organic product that would result from reaction of 1-bromopropane with potassium tert-butoxide tert-butanol should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

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Answer 4

Question

Chapter 7.9, Problem 7.18E

(a)

Interpretation Introduction

Interpretation: The structure of major organic product and pathway followed that would result from reaction of 1-bromopropane with sodium cyanide in acetone should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

(b)

Interpretation Introduction

Interpretation: The structure of major organic product that would result from reaction of 1-bromopropane with sodium methoxide in methanol should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

(c)

Interpretation Introduction

Interpretation: The structure of major organic product that would result from reaction of 1-bromopropane with potassium tert-butoxide tert-butanol should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

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Answer 5

Chapter 7.9, Problem 7.18E

(a)

Interpretation Introduction

Interpretation: The structure of major organic product and pathway followed that would result from reaction of 1-bromopropane with sodium cyanide in acetone should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

(b)

Interpretation Introduction

Interpretation: The structure of major organic product that would result from reaction of 1-bromopropane with sodium methoxide in methanol should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

(c)

Interpretation Introduction

Interpretation: The structure of major organic product that would result from reaction of 1-bromopropane with potassium tert-butoxide tert-butanol should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

Answer 6

Chapter 7.9, Problem 7.18E

(a)

Interpretation Introduction

Interpretation: The structure of major organic product and pathway followed that would result from reaction of 1-bromopropane with sodium cyanide in acetone should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

Answer 7

Chapter 7.9, Problem 7.18E

(a)

Interpretation Introduction

Interpretation: The structure of major organic product and pathway followed that would result from reaction of 1-bromopropane with sodium cyanide in acetone should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

Answer 8

(b)

Interpretation Introduction

Interpretation: The structure of major organic product that would result from reaction of 1-bromopropane with sodium methoxide in methanol should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

Answer 9

(b)

Interpretation Introduction

Interpretation: The structure of major organic product that would result from reaction of 1-bromopropane with sodium methoxide in methanol should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

Answer 10

(c)

Interpretation Introduction

Interpretation: The structure of major organic product that would result from reaction of 1-bromopropane with potassium tert-butoxide tert-butanol should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

Answer 11

(c)

Interpretation Introduction

Interpretation: The structure of major organic product that would result from reaction of 1-bromopropane with potassium tert-butoxide tert-butanol should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

Answer 12

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Answer 15

Ch. 7.1 - Prob. 7.1E Ch. 7.2 - Prob. 7.2E Ch. 7.3 - Prob. 7.3E Ch. 7.3 - Prob. 7.5TIY Ch. 7.4 - Prob. 7.7TIY Ch. 7.5 - Prob. 7.9TIY Ch. 7.6 - Prob. 7.10E Ch. 7.7 - Prob. 7.11E Ch. 7.7 - Prob. 7.12E Ch. 7.7 - Prob. 7.13E

Solution Summary: The author explains the structure of major organic product and pathway followed from reaction of 1-bromopropane with sodium cyanide in acetone.

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