a) Interpretation: Whether the reaction shown will result in an optically active product is to be stated. Concept introduction: The catalytic hydrogenation is a heterogeneous process that occurs with syn stereochemistry. Both the hydrogens add from the same face of the double bond from the catalytic surface. To state: Whether the reaction shown will result in an optically active product.

Question

. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B 2°C. +2°C. < cleavage Bond A • CH3 + 26. t cleavage 2°C• +3°C• Bond C Cleavage CH3 ZC '2°C. 26. E Strongest 3°C. 2C. Gund Largest BDE weakest bond In that molecule a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest C bond Produces A Weakest Bond Most Strongest Bond Stable radical Strongest Gund produces least stable radicals b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. 人 8°C. formed in bound C cleavage ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. methyl radical •CH3 formed in bund A Cleavage

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 8.SE, Problem 32MP

Interpretation Introduction

a)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

The catalytic hydrogenation is a heterogeneous process that occurs with syn stereochemistry. Both the hydrogens add from the same face of the double bond from the catalytic surface.

To state:

Whether the reaction shown will result in an optically active product.

Interpretation Introduction

b)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

The epoxide ring opening reaction takes place in two steps. In the first step protonation of the epoxide oxygen takes place. In the second step the nucleophilic attack of water on the protonated epoxide takes place from the less shielded side to give a trans-I,2-diol as the product. If the product contains a chiral centre it will be optically active.

To state:

Whether the reaction shown will result in an optically inactive product.

Interpretation Introduction

c)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

During ozonolysis the double bond in alkene is cleaved and carbonyl compounds usually result. When the carbon in the double bond is disubstituted, ketones are produced. When it is monosubstituted, an aldehyde is the product. If the alkene has a terminal double bond then formaldehyde is the product.

To state:

Whether the reaction shown will result in an optically active product.

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. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B 2°C. +2°C. < cleavage Bond A • CH3 + 26. t cleavage 2°C• +3°C• Bond C Cleavage CH3 ZC '2°C. 26. E Strongest 3°C. 2C. Gund Largest BDE weakest bond In that molecule a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest C bond Produces A Weakest Bond Most Strongest Bond Stable radical Strongest Gund produces least stable radicals b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. 人 8°C. formed in bound C cleavage ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. methyl radical •CH3 formed in bund A Cleavage

Which carbocation is more stable?

Are the products of the given reaction correct? Why or why not?

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 8.SE, Problem 32MP

Interpretation Introduction

a)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

The catalytic hydrogenation is a heterogeneous process that occurs with syn stereochemistry. Both the hydrogens add from the same face of the double bond from the catalytic surface.

To state:

Whether the reaction shown will result in an optically active product.

Interpretation Introduction

b)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

The epoxide ring opening reaction takes place in two steps. In the first step protonation of the epoxide oxygen takes place. In the second step the nucleophilic attack of water on the protonated epoxide takes place from the less shielded side to give a trans-I,2-diol as the product. If the product contains a chiral centre it will be optically active.

To state:

Whether the reaction shown will result in an optically inactive product.

Interpretation Introduction

c)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

During ozonolysis the double bond in alkene is cleaved and carbonyl compounds usually result. When the carbon in the double bond is disubstituted, ketones are produced. When it is monosubstituted, an aldehyde is the product. If the alkene has a terminal double bond then formaldehyde is the product.

To state:

Whether the reaction shown will result in an optically active product.

Expert Solution & Answer

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Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 8.SE, Problem 32MP

Interpretation Introduction

a)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

The catalytic hydrogenation is a heterogeneous process that occurs with syn stereochemistry. Both the hydrogens add from the same face of the double bond from the catalytic surface.

To state:

Whether the reaction shown will result in an optically active product.

Interpretation Introduction

b)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

The epoxide ring opening reaction takes place in two steps. In the first step protonation of the epoxide oxygen takes place. In the second step the nucleophilic attack of water on the protonated epoxide takes place from the less shielded side to give a trans-I,2-diol as the product. If the product contains a chiral centre it will be optically active.

To state:

Whether the reaction shown will result in an optically inactive product.

Interpretation Introduction

c)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

During ozonolysis the double bond in alkene is cleaved and carbonyl compounds usually result. When the carbon in the double bond is disubstituted, ketones are produced. When it is monosubstituted, an aldehyde is the product. If the alkene has a terminal double bond then formaldehyde is the product.

To state:

Whether the reaction shown will result in an optically active product.

Expert Solution & Answer

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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 8.SE, Problem 32MP

Interpretation Introduction

a)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

The catalytic hydrogenation is a heterogeneous process that occurs with syn stereochemistry. Both the hydrogens add from the same face of the double bond from the catalytic surface.

To state:

Whether the reaction shown will result in an optically active product.

Interpretation Introduction

b)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

The epoxide ring opening reaction takes place in two steps. In the first step protonation of the epoxide oxygen takes place. In the second step the nucleophilic attack of water on the protonated epoxide takes place from the less shielded side to give a trans-I,2-diol as the product. If the product contains a chiral centre it will be optically active.

To state:

Whether the reaction shown will result in an optically inactive product.

Interpretation Introduction

c)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

During ozonolysis the double bond in alkene is cleaved and carbonyl compounds usually result. When the carbon in the double bond is disubstituted, ketones are produced. When it is monosubstituted, an aldehyde is the product. If the alkene has a terminal double bond then formaldehyde is the product.

To state:

Whether the reaction shown will result in an optically active product.

Expert Solution & Answer

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Answer 5

Chapter 8.SE, Problem 32MP

Interpretation Introduction

a)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

The catalytic hydrogenation is a heterogeneous process that occurs with syn stereochemistry. Both the hydrogens add from the same face of the double bond from the catalytic surface.

To state:

Whether the reaction shown will result in an optically active product.

Interpretation Introduction

b)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

The epoxide ring opening reaction takes place in two steps. In the first step protonation of the epoxide oxygen takes place. In the second step the nucleophilic attack of water on the protonated epoxide takes place from the less shielded side to give a trans-I,2-diol as the product. If the product contains a chiral centre it will be optically active.

To state:

Whether the reaction shown will result in an optically inactive product.

Interpretation Introduction

c)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

During ozonolysis the double bond in alkene is cleaved and carbonyl compounds usually result. When the carbon in the double bond is disubstituted, ketones are produced. When it is monosubstituted, an aldehyde is the product. If the alkene has a terminal double bond then formaldehyde is the product.

To state:

Whether the reaction shown will result in an optically active product.

Answer 6

Chapter 8.SE, Problem 32MP

Interpretation Introduction

a)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

The catalytic hydrogenation is a heterogeneous process that occurs with syn stereochemistry. Both the hydrogens add from the same face of the double bond from the catalytic surface.

To state:

Whether the reaction shown will result in an optically active product.

Answer 7

Chapter 8.SE, Problem 32MP

Interpretation Introduction

a)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

The catalytic hydrogenation is a heterogeneous process that occurs with syn stereochemistry. Both the hydrogens add from the same face of the double bond from the catalytic surface.

To state:

Whether the reaction shown will result in an optically active product.

Answer 8

Interpretation Introduction

b)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

The epoxide ring opening reaction takes place in two steps. In the first step protonation of the epoxide oxygen takes place. In the second step the nucleophilic attack of water on the protonated epoxide takes place from the less shielded side to give a trans-I,2-diol as the product. If the product contains a chiral centre it will be optically active.

To state:

Whether the reaction shown will result in an optically inactive product.

Answer 9

Interpretation Introduction

b)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

The epoxide ring opening reaction takes place in two steps. In the first step protonation of the epoxide oxygen takes place. In the second step the nucleophilic attack of water on the protonated epoxide takes place from the less shielded side to give a trans-I,2-diol as the product. If the product contains a chiral centre it will be optically active.

To state:

Whether the reaction shown will result in an optically inactive product.

Answer 10

Interpretation Introduction

c)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

During ozonolysis the double bond in alkene is cleaved and carbonyl compounds usually result. When the carbon in the double bond is disubstituted, ketones are produced. When it is monosubstituted, an aldehyde is the product. If the alkene has a terminal double bond then formaldehyde is the product.

To state:

Whether the reaction shown will result in an optically active product.

Answer 11

Interpretation Introduction

c)

Interpretation:

Whether the reaction shown will result in an optically active product is to be stated.

Concept introduction:

During ozonolysis the double bond in alkene is cleaved and carbonyl compounds usually result. When the carbon in the double bond is disubstituted, ketones are produced. When it is monosubstituted, an aldehyde is the product. If the alkene has a terminal double bond then formaldehyde is the product.

To state:

Whether the reaction shown will result in an optically active product.

Answer 12

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Answer 23

Ch. 8.1 - Prob. 1P Ch. 8.1 - How many alkene products, including E,Z isomers,...Ch. 8.2 - Prob. 3P Ch. 8.2 - Addition of HCl to 1, 2-dimethylcyclohexene yields...Ch. 8.3 - Prob. 5P Ch. 8.3 - Prob. 6P Ch. 8.4 - Prob. 7P Ch. 8.4 - From what alkenes might the following alcohols...Ch. 8.5 - Prob. 9P Ch. 8.5 - What alkenes might be used to prepare the...

Solution Summary: The author explains that catalytic hydrogenation is a heterogeneous process that occurs with syn stereochemistry.

Chapter 8 Solutions