The two structures of the sugar fructose are given. The cyclic structure predominates in aqueous solution. The number of carbon atoms present in the cyclic structure and the functional group at C2 in the cyclic form is to be identified. Concept introduction: Carbohydrates and the sugars mainly exist as cyclic acetals and hemiacetals. The formation of acetals is similar to imine formation and has two steps. First is the acid catalyzed addition of the alcohol to the carbonyl group. Second is substitution of the protonated hemiacetals.

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Answer 1

Question

Chapter 18, Problem 18.63SP

(a)

Interpretation Introduction

Interpretation:

The two structures of the sugar fructose are given. The cyclic structure predominates in aqueous solution. The number of carbon atoms present in the cyclic structure and the functional group at C2 in the cyclic form is to be identified.

Concept introduction:

Carbohydrates and the sugars mainly exist as cyclic acetals and hemiacetals. The formation of acetals is similar to imine formation and has two steps. First is the acid catalyzed addition of the alcohol to the carbonyl group. Second is substitution of the protonated hemiacetals.

(b)

Interpretation Introduction

Interpretation:

The two structures of the sugar fructose are given. The cyclic structure predominates in aqueous solution. A mechanism for the cyclization of the given sugar structure is to be predicted.

Concept introduction:

The steps followed by the cyclization are stated below:

The first step is the protonation of carbonyl group.

The second step is cyclization by the attack of lone pair of oxygen on the carbonyl carbon.

The third step is the deprotonation of cyclised fructose.

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Answer 2

Question

Chapter 18, Problem 18.63SP

(a)

Interpretation Introduction

Interpretation:

The two structures of the sugar fructose are given. The cyclic structure predominates in aqueous solution. The number of carbon atoms present in the cyclic structure and the functional group at C2 in the cyclic form is to be identified.

Concept introduction:

Carbohydrates and the sugars mainly exist as cyclic acetals and hemiacetals. The formation of acetals is similar to imine formation and has two steps. First is the acid catalyzed addition of the alcohol to the carbonyl group. Second is substitution of the protonated hemiacetals.

(b)

Interpretation Introduction

Interpretation:

The two structures of the sugar fructose are given. The cyclic structure predominates in aqueous solution. A mechanism for the cyclization of the given sugar structure is to be predicted.

Concept introduction:

The steps followed by the cyclization are stated below:

The first step is the protonation of carbonyl group.

The second step is cyclization by the attack of lone pair of oxygen on the carbonyl carbon.

The third step is the deprotonation of cyclised fructose.

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Answer 3

Question

Chapter 18, Problem 18.63SP

(a)

Interpretation Introduction

Interpretation:

The two structures of the sugar fructose are given. The cyclic structure predominates in aqueous solution. The number of carbon atoms present in the cyclic structure and the functional group at C2 in the cyclic form is to be identified.

Concept introduction:

Carbohydrates and the sugars mainly exist as cyclic acetals and hemiacetals. The formation of acetals is similar to imine formation and has two steps. First is the acid catalyzed addition of the alcohol to the carbonyl group. Second is substitution of the protonated hemiacetals.

(b)

Interpretation Introduction

Interpretation:

The two structures of the sugar fructose are given. The cyclic structure predominates in aqueous solution. A mechanism for the cyclization of the given sugar structure is to be predicted.

Concept introduction:

The steps followed by the cyclization are stated below:

The first step is the protonation of carbonyl group.

The second step is cyclization by the attack of lone pair of oxygen on the carbonyl carbon.

The third step is the deprotonation of cyclised fructose.

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Answer 4

Question

Chapter 18, Problem 18.63SP

(a)

Interpretation Introduction

Interpretation:

The two structures of the sugar fructose are given. The cyclic structure predominates in aqueous solution. The number of carbon atoms present in the cyclic structure and the functional group at C2 in the cyclic form is to be identified.

Concept introduction:

Carbohydrates and the sugars mainly exist as cyclic acetals and hemiacetals. The formation of acetals is similar to imine formation and has two steps. First is the acid catalyzed addition of the alcohol to the carbonyl group. Second is substitution of the protonated hemiacetals.

(b)

Interpretation Introduction

Interpretation:

The two structures of the sugar fructose are given. The cyclic structure predominates in aqueous solution. A mechanism for the cyclization of the given sugar structure is to be predicted.

Concept introduction:

The steps followed by the cyclization are stated below:

The first step is the protonation of carbonyl group.

The second step is cyclization by the attack of lone pair of oxygen on the carbonyl carbon.

The third step is the deprotonation of cyclised fructose.

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Answer 5

Chapter 18, Problem 18.63SP

(a)

Interpretation Introduction

Interpretation:

The two structures of the sugar fructose are given. The cyclic structure predominates in aqueous solution. The number of carbon atoms present in the cyclic structure and the functional group at C2 in the cyclic form is to be identified.

Concept introduction:

Carbohydrates and the sugars mainly exist as cyclic acetals and hemiacetals. The formation of acetals is similar to imine formation and has two steps. First is the acid catalyzed addition of the alcohol to the carbonyl group. Second is substitution of the protonated hemiacetals.

(b)

Interpretation Introduction

Interpretation:

The two structures of the sugar fructose are given. The cyclic structure predominates in aqueous solution. A mechanism for the cyclization of the given sugar structure is to be predicted.

Concept introduction:

The steps followed by the cyclization are stated below:

The first step is the protonation of carbonyl group.

The second step is cyclization by the attack of lone pair of oxygen on the carbonyl carbon.

The third step is the deprotonation of cyclised fructose.

Answer 6

Chapter 18, Problem 18.63SP

(a)

Interpretation Introduction

Interpretation:

The two structures of the sugar fructose are given. The cyclic structure predominates in aqueous solution. The number of carbon atoms present in the cyclic structure and the functional group at C2 in the cyclic form is to be identified.

Concept introduction:

Carbohydrates and the sugars mainly exist as cyclic acetals and hemiacetals. The formation of acetals is similar to imine formation and has two steps. First is the acid catalyzed addition of the alcohol to the carbonyl group. Second is substitution of the protonated hemiacetals.

Answer 7

Chapter 18, Problem 18.63SP

(a)

Interpretation Introduction

Interpretation:

The two structures of the sugar fructose are given. The cyclic structure predominates in aqueous solution. The number of carbon atoms present in the cyclic structure and the functional group at C2 in the cyclic form is to be identified.

Concept introduction:

Carbohydrates and the sugars mainly exist as cyclic acetals and hemiacetals. The formation of acetals is similar to imine formation and has two steps. First is the acid catalyzed addition of the alcohol to the carbonyl group. Second is substitution of the protonated hemiacetals.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The two structures of the sugar fructose are given. The cyclic structure predominates in aqueous solution. A mechanism for the cyclization of the given sugar structure is to be predicted.

Concept introduction:

The steps followed by the cyclization are stated below:

The first step is the protonation of carbonyl group.

The second step is cyclization by the attack of lone pair of oxygen on the carbonyl carbon.

The third step is the deprotonation of cyclised fructose.

Answer 9

(b)

Interpretation Introduction

Interpretation:

The two structures of the sugar fructose are given. The cyclic structure predominates in aqueous solution. A mechanism for the cyclization of the given sugar structure is to be predicted.

Concept introduction:

The steps followed by the cyclization are stated below:

The first step is the protonation of carbonyl group.

The second step is cyclization by the attack of lone pair of oxygen on the carbonyl carbon.

The third step is the deprotonation of cyclised fructose.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 18.3 - Give the IUPAC name and (if possible) a common...Ch. 18.5D - NMR spectra for two compounds are given here,...Ch. 18.5D - Why were no products from the McLafferty...Ch. 18.5D - Use equations to show the fragmentation leading to...Ch. 18.5E - Prob. 18.5P Ch. 18.7D - Show how you would synthesize each compound from...Ch. 18.8 - Prob. 18.7P Ch. 18.9 - Predict the products of the following reactions....Ch. 18.9 - Show how the following transformations may be...Ch. 18.10 - Prob. 18.10P

Solution Summary: The author explains the two structures of sugar fructose. The cyclic structure predominates in aqueous solution.

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Chapter 18 Solutions