(a) Interpretation: The structure of six-membered cyclic hemiacetal formed by 5-hydroxyhexanal should be drawn. Concept Introduction: Hemiacetal is a molecule formed by the addition of an alcohol to an aldehyde or ketone ,containing a carbon bonded to one −OH group and one −OR group. For example-

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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 17, Problem 17.71P

Interpretation Introduction

(a)

Interpretation:

The structure of six-membered cyclic hemiacetal formed by 5-hydroxyhexanal should be drawn.

Concept Introduction:

Hemiacetal is a molecule formed by the addition of an alcohol to an aldehyde or ketone,containing a carbon bonded to one −OH group and one −OR group. For example-

Expert Solution

Answer to Problem 17.71P

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 2

Explanation of Solution

Reaction of the aldehyde group and the hydroxyl group forms a six-membered cyclic hemiacetal.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 3

Therefore, the structure hemiacetal formed from 5-hydroxyhexanalis as follows:

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 4

Interpretation Introduction

(b)

Interpretation:

The number of possible stereoisomers of 5-hydroxyhexanal should be determined.

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Expert Solution

Answer to Problem 17.71P

5-hydroxyhexanal has 2 stereoisomers.

Explanation of Solution

For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 5

In 5-hydroxyhexanal, there is one stereocenter.

Therefore, number of stereoisomers can be calculated as follows:

Number of stereOisOmers = 2n = 21 = 2

Thus, number of stereoisomers will be 2.

Interpretation Introduction

(c)

Interpretation:

The number of possible stereoisomers of hemiacetal of 5-hydroxyhexanal should be calculated.

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Expert Solution

Answer to Problem 17.71P

Hemiacetal of 5-hydroxyhexanal has 4 stereoisomers.

Explanation of Solution

For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 6

In hemiacetal of 5-hydroxyhexanal, there are two stereo centres.

Therefore, number of stereoisomers can be calculated as follows:

Number of stereOisOmers = 2n = 22 = 4

Thus, number of stereoisomers are 4.

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With reference to the structures of acetylsalicylic acid (aspirin) and acetaminophen (the active ingredient in Tylenol), explain why acetaminophen tablets can be stored in the medicine cabinet for years, but aspirin tablets slowly decompose over time.

Ethyl butyrate, CH3CH2CH2CO2CH2CH3CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring. It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) Part A Given 7.30 gg of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100%% yield? Express your answer in grams to three significant figures. Part B A chemist ran the reaction and obtained 5.95 gg of ethyl butyrate. What was the percent yield? Express your answer as a percent to three significant figures. Part C The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0%% yield. How many grams would be produced from 7.30 gg of…

Ethyl butyrate, CH3CH2CH2CO2CH2CH3CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring. It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) Given 8.45 gg of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100%% yield? Express your answer in grams to three significant figures. A chemist ran the reaction and obtained 5.50 gg of ethyl butyrate. What was the percent yield? Express your answer as a percent to three significant figures. The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0%% yield. How many grams would be produced from 8.45 gg of butanoic acid and excess…

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 17, Problem 17.71P

Interpretation Introduction

(a)

Interpretation:

The structure of six-membered cyclic hemiacetal formed by 5-hydroxyhexanal should be drawn.

Concept Introduction:

Hemiacetal is a molecule formed by the addition of an alcohol to an aldehyde or ketone,containing a carbon bonded to one −OH group and one −OR group. For example-

Expert Solution

Answer to Problem 17.71P

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 2

Explanation of Solution

Reaction of the aldehyde group and the hydroxyl group forms a six-membered cyclic hemiacetal.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 3

Therefore, the structure hemiacetal formed from 5-hydroxyhexanalis as follows:

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 4

Interpretation Introduction

(b)

Interpretation:

The number of possible stereoisomers of 5-hydroxyhexanal should be determined.

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Expert Solution

Answer to Problem 17.71P

5-hydroxyhexanal has 2 stereoisomers.

Explanation of Solution

For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 5

In 5-hydroxyhexanal, there is one stereocenter.

Therefore, number of stereoisomers can be calculated as follows:

Number of stereOisOmers = 2n = 21 = 2

Thus, number of stereoisomers will be 2.

Interpretation Introduction

(c)

Interpretation:

The number of possible stereoisomers of hemiacetal of 5-hydroxyhexanal should be calculated.

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Expert Solution

Answer to Problem 17.71P

Hemiacetal of 5-hydroxyhexanal has 4 stereoisomers.

Explanation of Solution

For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 6

In hemiacetal of 5-hydroxyhexanal, there are two stereo centres.

Therefore, number of stereoisomers can be calculated as follows:

Number of stereOisOmers = 2n = 22 = 4

Thus, number of stereoisomers are 4.

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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 17, Problem 17.71P

Interpretation Introduction

(a)

Interpretation:

The structure of six-membered cyclic hemiacetal formed by 5-hydroxyhexanal should be drawn.

Concept Introduction:

Hemiacetal is a molecule formed by the addition of an alcohol to an aldehyde or ketone,containing a carbon bonded to one −OH group and one −OR group. For example-

Expert Solution

Answer to Problem 17.71P

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 2

Explanation of Solution

Reaction of the aldehyde group and the hydroxyl group forms a six-membered cyclic hemiacetal.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 3

Therefore, the structure hemiacetal formed from 5-hydroxyhexanalis as follows:

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 4

Interpretation Introduction

(b)

Interpretation:

The number of possible stereoisomers of 5-hydroxyhexanal should be determined.

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Expert Solution

Answer to Problem 17.71P

5-hydroxyhexanal has 2 stereoisomers.

Explanation of Solution

For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 5

In 5-hydroxyhexanal, there is one stereocenter.

Therefore, number of stereoisomers can be calculated as follows:

Number of stereOisOmers = 2n = 21 = 2

Thus, number of stereoisomers will be 2.

Interpretation Introduction

(c)

Interpretation:

The number of possible stereoisomers of hemiacetal of 5-hydroxyhexanal should be calculated.

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Expert Solution

Answer to Problem 17.71P

Hemiacetal of 5-hydroxyhexanal has 4 stereoisomers.

Explanation of Solution

For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 6

In hemiacetal of 5-hydroxyhexanal, there are two stereo centres.

Therefore, number of stereoisomers can be calculated as follows:

Number of stereOisOmers = 2n = 22 = 4

Thus, number of stereoisomers are 4.

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Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

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 17, Problem 17.71P

Interpretation Introduction

(a)

Interpretation:

The structure of six-membered cyclic hemiacetal formed by 5-hydroxyhexanal should be drawn.

Concept Introduction:

Hemiacetal is a molecule formed by the addition of an alcohol to an aldehyde or ketone,containing a carbon bonded to one −OH group and one −OR group. For example-

Expert Solution

Answer to Problem 17.71P

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 2

Explanation of Solution

Reaction of the aldehyde group and the hydroxyl group forms a six-membered cyclic hemiacetal.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 3

Therefore, the structure hemiacetal formed from 5-hydroxyhexanalis as follows:

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 4

Interpretation Introduction

(b)

Interpretation:

The number of possible stereoisomers of 5-hydroxyhexanal should be determined.

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Expert Solution

Answer to Problem 17.71P

5-hydroxyhexanal has 2 stereoisomers.

Explanation of Solution

For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 5

In 5-hydroxyhexanal, there is one stereocenter.

Therefore, number of stereoisomers can be calculated as follows:

Number of stereOisOmers = 2n = 21 = 2

Thus, number of stereoisomers will be 2.

Interpretation Introduction

(c)

Interpretation:

The number of possible stereoisomers of hemiacetal of 5-hydroxyhexanal should be calculated.

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Expert Solution

Answer to Problem 17.71P

Hemiacetal of 5-hydroxyhexanal has 4 stereoisomers.

Explanation of Solution

For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 6

In hemiacetal of 5-hydroxyhexanal, there are two stereo centres.

Therefore, number of stereoisomers can be calculated as follows:

Number of stereOisOmers = 2n = 22 = 4

Thus, number of stereoisomers are 4.

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Answer 5

Chapter 17, Problem 17.71P

Interpretation Introduction

(a)

Interpretation:

The structure of six-membered cyclic hemiacetal formed by 5-hydroxyhexanal should be drawn.

Concept Introduction:

Hemiacetal is a molecule formed by the addition of an alcohol to an aldehyde or ketone,containing a carbon bonded to one −OH group and one −OR group. For example-

Expert Solution

Answer to Problem 17.71P

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 2

Explanation of Solution

Reaction of the aldehyde group and the hydroxyl group forms a six-membered cyclic hemiacetal.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 3

Therefore, the structure hemiacetal formed from 5-hydroxyhexanalis as follows:

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 4

Interpretation Introduction

(b)

Interpretation:

The number of possible stereoisomers of 5-hydroxyhexanal should be determined.

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Expert Solution

Answer to Problem 17.71P

5-hydroxyhexanal has 2 stereoisomers.

Explanation of Solution

For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 5

In 5-hydroxyhexanal, there is one stereocenter.

Therefore, number of stereoisomers can be calculated as follows:

Number of stereOisOmers = 2n = 21 = 2

Thus, number of stereoisomers will be 2.

Interpretation Introduction

(c)

Interpretation:

The number of possible stereoisomers of hemiacetal of 5-hydroxyhexanal should be calculated.

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Expert Solution

Answer to Problem 17.71P

Hemiacetal of 5-hydroxyhexanal has 4 stereoisomers.

Explanation of Solution

For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 6

In hemiacetal of 5-hydroxyhexanal, there are two stereo centres.

Therefore, number of stereoisomers can be calculated as follows:

Number of stereOisOmers = 2n = 22 = 4

Thus, number of stereoisomers are 4.

Answer 6

Chapter 17, Problem 17.71P

Interpretation Introduction

(a)

Interpretation:

The structure of six-membered cyclic hemiacetal formed by 5-hydroxyhexanal should be drawn.

Concept Introduction:

Hemiacetal is a molecule formed by the addition of an alcohol to an aldehyde or ketone,containing a carbon bonded to one −OH group and one −OR group. For example-

Expert Solution

Answer to Problem 17.71P

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 2

Explanation of Solution

Reaction of the aldehyde group and the hydroxyl group forms a six-membered cyclic hemiacetal.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 3

Therefore, the structure hemiacetal formed from 5-hydroxyhexanalis as follows:

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 4

Answer 7

Chapter 17, Problem 17.71P

Interpretation Introduction

(a)

Interpretation:

The structure of six-membered cyclic hemiacetal formed by 5-hydroxyhexanal should be drawn.

Concept Introduction:

Hemiacetal is a molecule formed by the addition of an alcohol to an aldehyde or ketone,containing a carbon bonded to one −OH group and one −OR group. For example-

Answer 8

Expert Solution

Answer to Problem 17.71P

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 2

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

Reaction of the aldehyde group and the hydroxyl group forms a six-membered cyclic hemiacetal.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 3

Therefore, the structure hemiacetal formed from 5-hydroxyhexanalis as follows:

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 4

Answer 13

Interpretation Introduction

(b)

Interpretation:

The number of possible stereoisomers of 5-hydroxyhexanal should be determined.

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Expert Solution

Answer to Problem 17.71P

5-hydroxyhexanal has 2 stereoisomers.

Explanation of Solution

For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 5

In 5-hydroxyhexanal, there is one stereocenter.

Therefore, number of stereoisomers can be calculated as follows:

Number of stereOisOmers = 2n = 21 = 2

Thus, number of stereoisomers will be 2.

Answer 14

Interpretation Introduction

(b)

Interpretation:

The number of possible stereoisomers of 5-hydroxyhexanal should be determined.

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Answer 15

Expert Solution

Answer to Problem 17.71P

5-hydroxyhexanal has 2 stereoisomers.

Answer 16

Expert Solution

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Explanation of Solution

For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 5

In 5-hydroxyhexanal, there is one stereocenter.

Therefore, number of stereoisomers can be calculated as follows:

Number of stereOisOmers = 2n = 21 = 2

Thus, number of stereoisomers will be 2.

Answer 20

Interpretation Introduction

(c)

Interpretation:

The number of possible stereoisomers of hemiacetal of 5-hydroxyhexanal should be calculated.

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Expert Solution

Answer to Problem 17.71P

Hemiacetal of 5-hydroxyhexanal has 4 stereoisomers.

Explanation of Solution

For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 6

In hemiacetal of 5-hydroxyhexanal, there are two stereo centres.

Therefore, number of stereoisomers can be calculated as follows:

Number of stereOisOmers = 2n = 22 = 4

Thus, number of stereoisomers are 4.

Answer 21

Interpretation Introduction

(c)

Interpretation:

The number of possible stereoisomers of hemiacetal of 5-hydroxyhexanal should be calculated.

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Answer 22

Expert Solution

Answer to Problem 17.71P

Hemiacetal of 5-hydroxyhexanal has 4 stereoisomers.

Answer 23

Expert Solution

Answer 24

Expert Solution

Answer 25

Expert Solution

Answer 26

Explanation of Solution

For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip 6

In hemiacetal of 5-hydroxyhexanal, there are two stereo centres.

Therefore, number of stereoisomers can be calculated as follows:

Number of stereOisOmers = 2n = 22 = 4

Thus, number of stereoisomers are 4.

Answer 27

Ch. 17.2 - Problem 17-1 Wrtie the IUPAC name for each...Ch. 17.2 - Prob. 17.2P Ch. 17.2 - Prob. 17.3P Ch. 17.4 - Prob. 17.4P Ch. 17.4 - Prob. 17.5P Ch. 17.4 - Problem 17-6 Show the reaction of benzaldehyde...Ch. 17.4 - Problem 17-7 Identify all hemiacetals and acetals...Ch. 17.5 - Prob. 17.8P Ch. 17 - 17-9 Answer true or false. (a) The one aldehyde...Ch. 17 - Prob. 17.10P

Answer to Problem 17.71P

Explanation of Solution

(b) Interpretation: The number of possible stereoisomers of 5-hydroxyhexanal should be determined. Concept Introduction: Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Answer to Problem 17.71P

Explanation of Solution

Answer to Problem 17.71P

Explanation of Solution

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Chapter 17 Solutions