(a) Interpretation: The synthesis for ( CH 3 ) 2 CHCH 2 CH 2 CO 2 H from ( CH 3 ) 2 C = CH 2 ( 2 − methylpropene ) is to be stated. Concept introduction: The larger carbon chains can be synthesized from smaller carbon chains by reacting an epoxide with a Grignard reagent or organocuprate reagent. The alkyl part in the Grignard reagent acts as a nucleophile while the magnesium bromide acts as the electrophile. The reaction of an epoxide with Grignard reagent results in the formation of an alcohol. The alcohol on oxidation gives a carboxylic acid .

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Answer 1

Question

Chapter 11, Problem 11.40P

Interpretation Introduction

(a)

Interpretation:

The synthesis for (CH3)2CHCH2CH2CO2H from (CH3)2C=CH2 (2−methylpropene) is to be stated.

Concept introduction:

The larger carbon chains can be synthesized from smaller carbon chains by reacting an epoxide with a Grignard reagent or organocuprate reagent. The alkyl part in the Grignard reagent acts as a nucleophile while the magnesium bromide acts as the electrophile. The reaction of an epoxide with Grignard reagent results in the formation of an alcohol. The alcohol on oxidation gives a carboxylic acid.

Interpretation Introduction

(b)

Interpretation:

The synthesis for (CH3)2CHCO2H from 2-methylpropene is to be stated.

Concept introduction:

Hydroboration-oxidation reaction is the reaction in which an alkene reacts with borane in presence of a peroxide to yield primary alcohol. The reaction occurs by anti-markovnikov’s rule. Alcohol on oxidation with a strong oxidizing agent converts into a carboxylic acid.

Interpretation Introduction

(c)

Interpretation:

The synthesis for dibutyl sulfone from 1-butanethiol is to be stated.

Concept introduction:

Williamson ether synthesis is reaction in which an alkoxide reacts with an organohalide to form an ether. The reaction takes place by SN2 mechanism. Thiols, also, react with organohalides to form thiolether. The thiolethers on oxidation yields sulfones.

Interpretation Introduction

(d)

Interpretation:

The synthesis for (±) trans−1− ethoxy −2− methylcyclopentane from cyclopentene is to be stated.

Concept introduction:

Alkenes undergo concerted syn-addition reaction with MMPP reagent to form an epoxide. It is the reaction which takes place in a single step with complete retention of the configuration of the substrate. The reaction of an epoxide with a Grignard reagent or organocuprate reagent yields an alcohol. Alcohol on reaction with organohalide undergoes Williamson ether synthesis to yield ether.

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Transmitance 3. Which one of the following compounds corresponds to this IR spectrum? Point out the absorption band(s) that helped you decide. OH H3C OH H₂C CH3 H3C CH3 H3C INFRARED SPECTRUM 0.8- 0.6 0.4- 0.2 3000 2000 1000 Wavenumber (cm-1) 4. Consider this compound: H3C On the structure above, label the different types of H's as A, B, C, etc. In table form, list the labeled signals, and for each one state the number of hydrogens, their shifts, and the splitting you would observe for these hydrogens in the ¹H NMR spectrum. Label # of hydrogens splitting Shift (2)

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Answer 2

Question

Chapter 11, Problem 11.40P

Interpretation Introduction

(a)

Interpretation:

The synthesis for (CH3)2CHCH2CH2CO2H from (CH3)2C=CH2 (2−methylpropene) is to be stated.

Concept introduction:

The larger carbon chains can be synthesized from smaller carbon chains by reacting an epoxide with a Grignard reagent or organocuprate reagent. The alkyl part in the Grignard reagent acts as a nucleophile while the magnesium bromide acts as the electrophile. The reaction of an epoxide with Grignard reagent results in the formation of an alcohol. The alcohol on oxidation gives a carboxylic acid.

Interpretation Introduction

(b)

Interpretation:

The synthesis for (CH3)2CHCO2H from 2-methylpropene is to be stated.

Concept introduction:

Hydroboration-oxidation reaction is the reaction in which an alkene reacts with borane in presence of a peroxide to yield primary alcohol. The reaction occurs by anti-markovnikov’s rule. Alcohol on oxidation with a strong oxidizing agent converts into a carboxylic acid.

Interpretation Introduction

(c)

Interpretation:

The synthesis for dibutyl sulfone from 1-butanethiol is to be stated.

Concept introduction:

Williamson ether synthesis is reaction in which an alkoxide reacts with an organohalide to form an ether. The reaction takes place by SN2 mechanism. Thiols, also, react with organohalides to form thiolether. The thiolethers on oxidation yields sulfones.

Interpretation Introduction

(d)

Interpretation:

The synthesis for (±) trans−1− ethoxy −2− methylcyclopentane from cyclopentene is to be stated.

Concept introduction:

Alkenes undergo concerted syn-addition reaction with MMPP reagent to form an epoxide. It is the reaction which takes place in a single step with complete retention of the configuration of the substrate. The reaction of an epoxide with a Grignard reagent or organocuprate reagent yields an alcohol. Alcohol on reaction with organohalide undergoes Williamson ether synthesis to yield ether.

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Answer 3

Question

Chapter 11, Problem 11.40P

Interpretation Introduction

(a)

Interpretation:

The synthesis for (CH3)2CHCH2CH2CO2H from (CH3)2C=CH2 (2−methylpropene) is to be stated.

Concept introduction:

The larger carbon chains can be synthesized from smaller carbon chains by reacting an epoxide with a Grignard reagent or organocuprate reagent. The alkyl part in the Grignard reagent acts as a nucleophile while the magnesium bromide acts as the electrophile. The reaction of an epoxide with Grignard reagent results in the formation of an alcohol. The alcohol on oxidation gives a carboxylic acid.

Interpretation Introduction

(b)

Interpretation:

The synthesis for (CH3)2CHCO2H from 2-methylpropene is to be stated.

Concept introduction:

Hydroboration-oxidation reaction is the reaction in which an alkene reacts with borane in presence of a peroxide to yield primary alcohol. The reaction occurs by anti-markovnikov’s rule. Alcohol on oxidation with a strong oxidizing agent converts into a carboxylic acid.

Interpretation Introduction

(c)

Interpretation:

The synthesis for dibutyl sulfone from 1-butanethiol is to be stated.

Concept introduction:

Williamson ether synthesis is reaction in which an alkoxide reacts with an organohalide to form an ether. The reaction takes place by SN2 mechanism. Thiols, also, react with organohalides to form thiolether. The thiolethers on oxidation yields sulfones.

Interpretation Introduction

(d)

Interpretation:

The synthesis for (±) trans−1− ethoxy −2− methylcyclopentane from cyclopentene is to be stated.

Concept introduction:

Alkenes undergo concerted syn-addition reaction with MMPP reagent to form an epoxide. It is the reaction which takes place in a single step with complete retention of the configuration of the substrate. The reaction of an epoxide with a Grignard reagent or organocuprate reagent yields an alcohol. Alcohol on reaction with organohalide undergoes Williamson ether synthesis to yield ether.

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Answer 4

Question

Chapter 11, Problem 11.40P

Interpretation Introduction

(a)

Interpretation:

The synthesis for (CH3)2CHCH2CH2CO2H from (CH3)2C=CH2 (2−methylpropene) is to be stated.

Concept introduction:

The larger carbon chains can be synthesized from smaller carbon chains by reacting an epoxide with a Grignard reagent or organocuprate reagent. The alkyl part in the Grignard reagent acts as a nucleophile while the magnesium bromide acts as the electrophile. The reaction of an epoxide with Grignard reagent results in the formation of an alcohol. The alcohol on oxidation gives a carboxylic acid.

Interpretation Introduction

(b)

Interpretation:

The synthesis for (CH3)2CHCO2H from 2-methylpropene is to be stated.

Concept introduction:

Hydroboration-oxidation reaction is the reaction in which an alkene reacts with borane in presence of a peroxide to yield primary alcohol. The reaction occurs by anti-markovnikov’s rule. Alcohol on oxidation with a strong oxidizing agent converts into a carboxylic acid.

Interpretation Introduction

(c)

Interpretation:

The synthesis for dibutyl sulfone from 1-butanethiol is to be stated.

Concept introduction:

Williamson ether synthesis is reaction in which an alkoxide reacts with an organohalide to form an ether. The reaction takes place by SN2 mechanism. Thiols, also, react with organohalides to form thiolether. The thiolethers on oxidation yields sulfones.

Interpretation Introduction

(d)

Interpretation:

The synthesis for (±) trans−1− ethoxy −2− methylcyclopentane from cyclopentene is to be stated.

Concept introduction:

Alkenes undergo concerted syn-addition reaction with MMPP reagent to form an epoxide. It is the reaction which takes place in a single step with complete retention of the configuration of the substrate. The reaction of an epoxide with a Grignard reagent or organocuprate reagent yields an alcohol. Alcohol on reaction with organohalide undergoes Williamson ether synthesis to yield ether.

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Answer 5

Chapter 11, Problem 11.40P

Interpretation Introduction

(a)

Interpretation:

The synthesis for (CH3)2CHCH2CH2CO2H from (CH3)2C=CH2 (2−methylpropene) is to be stated.

Concept introduction:

The larger carbon chains can be synthesized from smaller carbon chains by reacting an epoxide with a Grignard reagent or organocuprate reagent. The alkyl part in the Grignard reagent acts as a nucleophile while the magnesium bromide acts as the electrophile. The reaction of an epoxide with Grignard reagent results in the formation of an alcohol. The alcohol on oxidation gives a carboxylic acid.

Interpretation Introduction

(b)

Interpretation:

The synthesis for (CH3)2CHCO2H from 2-methylpropene is to be stated.

Concept introduction:

Hydroboration-oxidation reaction is the reaction in which an alkene reacts with borane in presence of a peroxide to yield primary alcohol. The reaction occurs by anti-markovnikov’s rule. Alcohol on oxidation with a strong oxidizing agent converts into a carboxylic acid.

Interpretation Introduction

(c)

Interpretation:

The synthesis for dibutyl sulfone from 1-butanethiol is to be stated.

Concept introduction:

Williamson ether synthesis is reaction in which an alkoxide reacts with an organohalide to form an ether. The reaction takes place by SN2 mechanism. Thiols, also, react with organohalides to form thiolether. The thiolethers on oxidation yields sulfones.

Interpretation Introduction

(d)

Interpretation:

The synthesis for (±) trans−1− ethoxy −2− methylcyclopentane from cyclopentene is to be stated.

Concept introduction:

Alkenes undergo concerted syn-addition reaction with MMPP reagent to form an epoxide. It is the reaction which takes place in a single step with complete retention of the configuration of the substrate. The reaction of an epoxide with a Grignard reagent or organocuprate reagent yields an alcohol. Alcohol on reaction with organohalide undergoes Williamson ether synthesis to yield ether.

Answer 6

Chapter 11, Problem 11.40P

Interpretation Introduction

(a)

Interpretation:

The synthesis for (CH3)2CHCH2CH2CO2H from (CH3)2C=CH2 (2−methylpropene) is to be stated.

Concept introduction:

The larger carbon chains can be synthesized from smaller carbon chains by reacting an epoxide with a Grignard reagent or organocuprate reagent. The alkyl part in the Grignard reagent acts as a nucleophile while the magnesium bromide acts as the electrophile. The reaction of an epoxide with Grignard reagent results in the formation of an alcohol. The alcohol on oxidation gives a carboxylic acid.

Answer 7

Chapter 11, Problem 11.40P

Interpretation Introduction

(a)

Interpretation:

The synthesis for (CH3)2CHCH2CH2CO2H from (CH3)2C=CH2 (2−methylpropene) is to be stated.

Concept introduction:

The larger carbon chains can be synthesized from smaller carbon chains by reacting an epoxide with a Grignard reagent or organocuprate reagent. The alkyl part in the Grignard reagent acts as a nucleophile while the magnesium bromide acts as the electrophile. The reaction of an epoxide with Grignard reagent results in the formation of an alcohol. The alcohol on oxidation gives a carboxylic acid.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The synthesis for (CH3)2CHCO2H from 2-methylpropene is to be stated.

Concept introduction:

Hydroboration-oxidation reaction is the reaction in which an alkene reacts with borane in presence of a peroxide to yield primary alcohol. The reaction occurs by anti-markovnikov’s rule. Alcohol on oxidation with a strong oxidizing agent converts into a carboxylic acid.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The synthesis for (CH3)2CHCO2H from 2-methylpropene is to be stated.

Concept introduction:

Hydroboration-oxidation reaction is the reaction in which an alkene reacts with borane in presence of a peroxide to yield primary alcohol. The reaction occurs by anti-markovnikov’s rule. Alcohol on oxidation with a strong oxidizing agent converts into a carboxylic acid.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The synthesis for dibutyl sulfone from 1-butanethiol is to be stated.

Concept introduction:

Williamson ether synthesis is reaction in which an alkoxide reacts with an organohalide to form an ether. The reaction takes place by SN2 mechanism. Thiols, also, react with organohalides to form thiolether. The thiolethers on oxidation yields sulfones.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The synthesis for dibutyl sulfone from 1-butanethiol is to be stated.

Concept introduction:

Williamson ether synthesis is reaction in which an alkoxide reacts with an organohalide to form an ether. The reaction takes place by SN2 mechanism. Thiols, also, react with organohalides to form thiolether. The thiolethers on oxidation yields sulfones.

Answer 12

Interpretation Introduction

(d)

Interpretation:

The synthesis for (±) trans−1− ethoxy −2− methylcyclopentane from cyclopentene is to be stated.

Concept introduction:

Alkenes undergo concerted syn-addition reaction with MMPP reagent to form an epoxide. It is the reaction which takes place in a single step with complete retention of the configuration of the substrate. The reaction of an epoxide with a Grignard reagent or organocuprate reagent yields an alcohol. Alcohol on reaction with organohalide undergoes Williamson ether synthesis to yield ether.

Answer 13

Interpretation Introduction

(d)

Interpretation:

The synthesis for (±) trans−1− ethoxy −2− methylcyclopentane from cyclopentene is to be stated.

Concept introduction:

Alkenes undergo concerted syn-addition reaction with MMPP reagent to form an epoxide. It is the reaction which takes place in a single step with complete retention of the configuration of the substrate. The reaction of an epoxide with a Grignard reagent or organocuprate reagent yields an alcohol. Alcohol on reaction with organohalide undergoes Williamson ether synthesis to yield ether.

Answer 14

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Answer 15

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Answer 16

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Answer 17

Ch. 11 - Prob. 11.1P Ch. 11 - Prob. 11.2P Ch. 11 - Prob. 11.3P Ch. 11 - Prob. 11.4P Ch. 11 - Prob. 11.5P Ch. 11 - Prob. 11.6P Ch. 11 - Prob. 11.7P Ch. 11 - Prob. 11.8P Ch. 11 - Prob. 11.9P Ch. 11 - Prob. 11.10P

Solution Summary: The author explains how larger carbon chains can be synthesized from smaller carbon chain by reacting an epoxide with a Grignard reagent.

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Chapter 11 Solutions