a) Interpretation: The major product obtainable from addition of HBr to methylidenecyclohexane is to be predicted. Concept introduction: The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product. To predict: The major product obtainable from addition of HBr to methylidenecyclohexane.

Question

5. A solution of sucrose is fermented in a vessel until the evolution of CO2 ceases. Then, the product solution is analyzed and found to contain, 45% ethanol; 5% acetic acid; and 15% glycerin by weight. If the original charge is 500 kg, evaluate; e. The ratio of sucrose to water in the original charge (wt/wt). f. Moles of CO2 evolved. g. Maximum possible amount of ethanol that could be formed. h. Conversion efficiency. i. Per cent excess of excess reactant. Reactions: Inversion reaction: C12H22O11 + H2O →2C6H12O6 Fermentation reaction: C6H12O6 →→2C2H5OH + 2CO2 Formation of acetic acid and glycerin: C6H12O6 + C2H5OH + H₂O→ CH3COOH + 2C3H8O3

Answer 1

Question

Chapter 7.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The major product obtainable from addition of HBr to methylidenecyclohexane is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to methylidenecyclohexane.

Interpretation Introduction

b)

Interpretation:

The major product obtainable from addition of HBr to the octahydronaphthalene is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to octahydronaphthalene.

Interpretation Introduction

c)

Interpretation:

The major product obtainable from addition of HBr to 4-methyl-2-pentene is to be predicted.

Concept introduction:

In electrophilic addition reactions, the first step is the attack of the π electrons of the double bond on the hydrogen of another reactant to yield a carbocation. One of the carbon in C=C gets attached to hydrogen while the other acquires a positive charge. In the second step, the carbocation formed can rearrange to give another more stable carbocation either by a hydride shift (shift of hydrogen atom with its electron pair) or by an alkyl shift (shift of an alkyl group with its electron pair) between neighboring carbons. In the last step the carbocation produced reacts with a negatively charged ion or eliminates a proton to give the product.

To give:

The major product obtainable from addition of HBr to 4-methyl-2-pentene.

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5. A solution of sucrose is fermented in a vessel until the evolution of CO2 ceases. Then, the product solution is analyzed and found to contain, 45% ethanol; 5% acetic acid; and 15% glycerin by weight. If the original charge is 500 kg, evaluate; e. The ratio of sucrose to water in the original charge (wt/wt). f. Moles of CO2 evolved. g. Maximum possible amount of ethanol that could be formed. h. Conversion efficiency. i. Per cent excess of excess reactant. Reactions: Inversion reaction: C12H22O11 + H2O →2C6H12O6 Fermentation reaction: C6H12O6 →→2C2H5OH + 2CO2 Formation of acetic acid and glycerin: C6H12O6 + C2H5OH + H₂O→ CH3COOH + 2C3H8O3

Show work. don't give Ai generated solution. How many carbons and hydrogens are in the structure?

13. (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.← Cleavage 2°C. + Bond C +3°C• CH3 2C Cleavage E 2°C. 26. weakest bond Intact molecule Strongest 3°C 20. Gund Largest argest a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. C Weakest bond A Produces Most Bond Strongest Bond Strongest Gund produces least stable radicals Weakest Stable radical 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. 13°C. formed in bound C cleavage ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. • CH3 methyl radical Formed in Gund A Cleavage c.…

Answer 2

Question

Chapter 7.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The major product obtainable from addition of HBr to methylidenecyclohexane is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to methylidenecyclohexane.

Interpretation Introduction

b)

Interpretation:

The major product obtainable from addition of HBr to the octahydronaphthalene is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to octahydronaphthalene.

Interpretation Introduction

c)

Interpretation:

The major product obtainable from addition of HBr to 4-methyl-2-pentene is to be predicted.

Concept introduction:

In electrophilic addition reactions, the first step is the attack of the π electrons of the double bond on the hydrogen of another reactant to yield a carbocation. One of the carbon in C=C gets attached to hydrogen while the other acquires a positive charge. In the second step, the carbocation formed can rearrange to give another more stable carbocation either by a hydride shift (shift of hydrogen atom with its electron pair) or by an alkyl shift (shift of an alkyl group with its electron pair) between neighboring carbons. In the last step the carbocation produced reacts with a negatively charged ion or eliminates a proton to give the product.

To give:

The major product obtainable from addition of HBr to 4-methyl-2-pentene.

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Answer 3

Question

Chapter 7.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The major product obtainable from addition of HBr to methylidenecyclohexane is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to methylidenecyclohexane.

Interpretation Introduction

b)

Interpretation:

The major product obtainable from addition of HBr to the octahydronaphthalene is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to octahydronaphthalene.

Interpretation Introduction

c)

Interpretation:

The major product obtainable from addition of HBr to 4-methyl-2-pentene is to be predicted.

Concept introduction:

In electrophilic addition reactions, the first step is the attack of the π electrons of the double bond on the hydrogen of another reactant to yield a carbocation. One of the carbon in C=C gets attached to hydrogen while the other acquires a positive charge. In the second step, the carbocation formed can rearrange to give another more stable carbocation either by a hydride shift (shift of hydrogen atom with its electron pair) or by an alkyl shift (shift of an alkyl group with its electron pair) between neighboring carbons. In the last step the carbocation produced reacts with a negatively charged ion or eliminates a proton to give the product.

To give:

The major product obtainable from addition of HBr to 4-methyl-2-pentene.

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Answer 4

Question

Chapter 7.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The major product obtainable from addition of HBr to methylidenecyclohexane is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to methylidenecyclohexane.

Interpretation Introduction

b)

Interpretation:

The major product obtainable from addition of HBr to the octahydronaphthalene is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to octahydronaphthalene.

Interpretation Introduction

c)

Interpretation:

The major product obtainable from addition of HBr to 4-methyl-2-pentene is to be predicted.

Concept introduction:

In electrophilic addition reactions, the first step is the attack of the π electrons of the double bond on the hydrogen of another reactant to yield a carbocation. One of the carbon in C=C gets attached to hydrogen while the other acquires a positive charge. In the second step, the carbocation formed can rearrange to give another more stable carbocation either by a hydride shift (shift of hydrogen atom with its electron pair) or by an alkyl shift (shift of an alkyl group with its electron pair) between neighboring carbons. In the last step the carbocation produced reacts with a negatively charged ion or eliminates a proton to give the product.

To give:

The major product obtainable from addition of HBr to 4-methyl-2-pentene.

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Answer 5

Chapter 7.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The major product obtainable from addition of HBr to methylidenecyclohexane is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to methylidenecyclohexane.

Interpretation Introduction

b)

Interpretation:

The major product obtainable from addition of HBr to the octahydronaphthalene is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to octahydronaphthalene.

Interpretation Introduction

c)

Interpretation:

The major product obtainable from addition of HBr to 4-methyl-2-pentene is to be predicted.

Concept introduction:

In electrophilic addition reactions, the first step is the attack of the π electrons of the double bond on the hydrogen of another reactant to yield a carbocation. One of the carbon in C=C gets attached to hydrogen while the other acquires a positive charge. In the second step, the carbocation formed can rearrange to give another more stable carbocation either by a hydride shift (shift of hydrogen atom with its electron pair) or by an alkyl shift (shift of an alkyl group with its electron pair) between neighboring carbons. In the last step the carbocation produced reacts with a negatively charged ion or eliminates a proton to give the product.

To give:

The major product obtainable from addition of HBr to 4-methyl-2-pentene.

Answer 6

Chapter 7.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The major product obtainable from addition of HBr to methylidenecyclohexane is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to methylidenecyclohexane.

Answer 7

Chapter 7.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The major product obtainable from addition of HBr to methylidenecyclohexane is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to methylidenecyclohexane.

Answer 8

Interpretation Introduction

b)

Interpretation:

The major product obtainable from addition of HBr to the octahydronaphthalene is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to octahydronaphthalene.

Answer 9

Interpretation Introduction

b)

Interpretation:

The major product obtainable from addition of HBr to the octahydronaphthalene is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to octahydronaphthalene.

Answer 10

Interpretation Introduction

c)

Interpretation:

The major product obtainable from addition of HBr to 4-methyl-2-pentene is to be predicted.

Concept introduction:

In electrophilic addition reactions, the first step is the attack of the π electrons of the double bond on the hydrogen of another reactant to yield a carbocation. One of the carbon in C=C gets attached to hydrogen while the other acquires a positive charge. In the second step, the carbocation formed can rearrange to give another more stable carbocation either by a hydride shift (shift of hydrogen atom with its electron pair) or by an alkyl shift (shift of an alkyl group with its electron pair) between neighboring carbons. In the last step the carbocation produced reacts with a negatively charged ion or eliminates a proton to give the product.

To give:

The major product obtainable from addition of HBr to 4-methyl-2-pentene.

Answer 11

Interpretation Introduction

c)

Interpretation:

The major product obtainable from addition of HBr to 4-methyl-2-pentene is to be predicted.

Concept introduction:

In electrophilic addition reactions, the first step is the attack of the π electrons of the double bond on the hydrogen of another reactant to yield a carbocation. One of the carbon in C=C gets attached to hydrogen while the other acquires a positive charge. In the second step, the carbocation formed can rearrange to give another more stable carbocation either by a hydride shift (shift of hydrogen atom with its electron pair) or by an alkyl shift (shift of an alkyl group with its electron pair) between neighboring carbons. In the last step the carbocation produced reacts with a negatively charged ion or eliminates a proton to give the product.

To give:

The major product obtainable from addition of HBr to 4-methyl-2-pentene.

Answer 12

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Answer 23

Ch. 7.2 - Calculate the degree of unsaturation in each of...Ch. 7.2 - Prob. 2P Ch. 7.2 - Diazepam, marketed as an antianxiety medication...Ch. 7.3 - Give IUPAC names for the following compounds:Ch. 7.3 - Prob. 5P Ch. 7.3 - Prob. 6P Ch. 7.3 - Prob. 7P Ch. 7.4 - Prob. 8P Ch. 7.4 - Prob. 9P Ch. 7.4 - Prob. 10P

Solution Summary: The author explains the major product obtainable from addition of HBr to methylidenecyclohexane.

Chapter 7 Solutions