a) Interpretation: Among the two alcohols, 1-propanol and 2-propanol, which will react faster with HX to form the corresponding alkyl halide is to be stated. Concept introduction: Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary. To state: Among the two alcohols, 1-propanol and 2-propanol, which will react faster with HX to form the corresponding alkyl halide.

Question

Q4. Alkyl halides are good at doing substitution (SN2/SN1) and elimination (E1/E2) reactions because the halide (X-) is a good LG. Alcohols on the other hand are not suitable for these reactions since hydroxide (¯OH) is a poor LG. However, an OH can be converted into a OTs (tosyl group) by reacting an alcohol with TsCl in presence of a base. An OTs is a good LG, and this allows us to indirectly (via OTs) use alcohols in substitution (SN2/SN1) and elimination (E1/E2) reactions. (4) OH TsCl NEt3 OTS Tosyl ester NaCN DMSO + HNEt3 Determine the major/minor products CH3OH heat OTS Tosyl ester TsCl = NaOCH3 CH3OH DBU Ś=0 CI

Answer 1

Question

Chapter 10.SE, Problem 49AP

Interpretation Introduction

a)

Interpretation:

Among the two alcohols, 1-propanol and 2-propanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 1-propanol and 2-propanol, which will react faster with HX to form the corresponding alkyl halide.

Interpretation Introduction

b)

Interpretation:

Among the two alcohols, 1-methylcyclopentanol and 2-methylcyclopentanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 1-methylcyclopentanol and 2-methylcyclopentanol, which will react faster with HX to form the corresponding alkyl halide.

Interpretation Introduction

c)

Interpretation:

Among the two alcohols, 2,2-dimethyl-1-propanol and 2-methyl-2-butanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 2,2-dimethyl-1-propanol and 2-methyl-2-butanol, which will react faster with HX to form the corresponding alkyl halide.

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Q4. Alkyl halides are good at doing substitution (SN2/SN1) and elimination (E1/E2) reactions because the halide (X-) is a good LG. Alcohols on the other hand are not suitable for these reactions since hydroxide (¯OH) is a poor LG. However, an OH can be converted into a OTs (tosyl group) by reacting an alcohol with TsCl in presence of a base. An OTs is a good LG, and this allows us to indirectly (via OTs) use alcohols in substitution (SN2/SN1) and elimination (E1/E2) reactions. (4) OH TsCl NEt3 OTS Tosyl ester NaCN DMSO + HNEt3 Determine the major/minor products CH3OH heat OTS Tosyl ester TsCl = NaOCH3 CH3OH DBU Ś=0 CI

2. The following carbocation is generated as an intermediate in the addition of H-Br to an alkene. Draw the structure of all possible alkenes that could have formed this intermediate.

Draw the structure of the major product of the reaction shown above.

Answer 2

Question

Chapter 10.SE, Problem 49AP

Interpretation Introduction

a)

Interpretation:

Among the two alcohols, 1-propanol and 2-propanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 1-propanol and 2-propanol, which will react faster with HX to form the corresponding alkyl halide.

Interpretation Introduction

b)

Interpretation:

Among the two alcohols, 1-methylcyclopentanol and 2-methylcyclopentanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 1-methylcyclopentanol and 2-methylcyclopentanol, which will react faster with HX to form the corresponding alkyl halide.

Interpretation Introduction

c)

Interpretation:

Among the two alcohols, 2,2-dimethyl-1-propanol and 2-methyl-2-butanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 2,2-dimethyl-1-propanol and 2-methyl-2-butanol, which will react faster with HX to form the corresponding alkyl halide.

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Answer 3

Question

Chapter 10.SE, Problem 49AP

Interpretation Introduction

a)

Interpretation:

Among the two alcohols, 1-propanol and 2-propanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 1-propanol and 2-propanol, which will react faster with HX to form the corresponding alkyl halide.

Interpretation Introduction

b)

Interpretation:

Among the two alcohols, 1-methylcyclopentanol and 2-methylcyclopentanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 1-methylcyclopentanol and 2-methylcyclopentanol, which will react faster with HX to form the corresponding alkyl halide.

Interpretation Introduction

c)

Interpretation:

Among the two alcohols, 2,2-dimethyl-1-propanol and 2-methyl-2-butanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 2,2-dimethyl-1-propanol and 2-methyl-2-butanol, which will react faster with HX to form the corresponding alkyl halide.

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Answer 4

Question

Chapter 10.SE, Problem 49AP

Interpretation Introduction

a)

Interpretation:

Among the two alcohols, 1-propanol and 2-propanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 1-propanol and 2-propanol, which will react faster with HX to form the corresponding alkyl halide.

Interpretation Introduction

b)

Interpretation:

Among the two alcohols, 1-methylcyclopentanol and 2-methylcyclopentanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 1-methylcyclopentanol and 2-methylcyclopentanol, which will react faster with HX to form the corresponding alkyl halide.

Interpretation Introduction

c)

Interpretation:

Among the two alcohols, 2,2-dimethyl-1-propanol and 2-methyl-2-butanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 2,2-dimethyl-1-propanol and 2-methyl-2-butanol, which will react faster with HX to form the corresponding alkyl halide.

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Answer 5

Chapter 10.SE, Problem 49AP

Interpretation Introduction

a)

Interpretation:

Among the two alcohols, 1-propanol and 2-propanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 1-propanol and 2-propanol, which will react faster with HX to form the corresponding alkyl halide.

Interpretation Introduction

b)

Interpretation:

Among the two alcohols, 1-methylcyclopentanol and 2-methylcyclopentanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 1-methylcyclopentanol and 2-methylcyclopentanol, which will react faster with HX to form the corresponding alkyl halide.

Interpretation Introduction

c)

Interpretation:

Among the two alcohols, 2,2-dimethyl-1-propanol and 2-methyl-2-butanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 2,2-dimethyl-1-propanol and 2-methyl-2-butanol, which will react faster with HX to form the corresponding alkyl halide.

Answer 6

Chapter 10.SE, Problem 49AP

Interpretation Introduction

a)

Interpretation:

Among the two alcohols, 1-propanol and 2-propanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 1-propanol and 2-propanol, which will react faster with HX to form the corresponding alkyl halide.

Answer 7

Chapter 10.SE, Problem 49AP

Interpretation Introduction

a)

Interpretation:

Among the two alcohols, 1-propanol and 2-propanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 1-propanol and 2-propanol, which will react faster with HX to form the corresponding alkyl halide.

Answer 8

Interpretation Introduction

b)

Interpretation:

Among the two alcohols, 1-methylcyclopentanol and 2-methylcyclopentanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 1-methylcyclopentanol and 2-methylcyclopentanol, which will react faster with HX to form the corresponding alkyl halide.

Answer 9

Interpretation Introduction

b)

Interpretation:

Among the two alcohols, 1-methylcyclopentanol and 2-methylcyclopentanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 1-methylcyclopentanol and 2-methylcyclopentanol, which will react faster with HX to form the corresponding alkyl halide.

Answer 10

Interpretation Introduction

c)

Interpretation:

Among the two alcohols, 2,2-dimethyl-1-propanol and 2-methyl-2-butanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 2,2-dimethyl-1-propanol and 2-methyl-2-butanol, which will react faster with HX to form the corresponding alkyl halide.

Answer 11

Interpretation Introduction

c)

Interpretation:

Among the two alcohols, 2,2-dimethyl-1-propanol and 2-methyl-2-butanol, which will react faster with HX to form the corresponding alkyl halide is to be stated.

Concept introduction:

Alcohols react with HX to yield the corresponding alkyl halide. The order of reactivity is methyl < primary < secondary < tertiary.

To state:

Among the two alcohols, 2,2-dimethyl-1-propanol and 2-methyl-2-butanol, which will react faster with HX to form the corresponding alkyl halide.

Answer 12

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Answer 23

Ch. 10.1 - Prob. 1P Ch. 10.1 - Draw structures corresponding to the following...Ch. 10.2 - Prob. 3P Ch. 10.2 - Taking the relative reactivities of 1Â°, 2Â°, and...Ch. 10.4 - Prob. 5P Ch. 10.4 - The major product of the reaction of...Ch. 10.4 - Prob. 7P Ch. 10.5 - Prob. 8P Ch. 10.6 - Prob. 9P Ch. 10.6 - How might you replace a halogen substituent by a...

Solution Summary: The author explains that alcohols react with HX to yield the corresponding alkyl halide.

Chapter 10 Solutions