The structure of 2 -ketohexose is to be determined. Concept introduction: The aldehyde carbonyl group and ketone carbonyl group reduces to alcohol on reaction with NaBH 4 . The C = O group changes to C − OH on reduction.

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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 26.9, Problem 20P

Interpretation Introduction

Interpretation: The structure of 2-ketohexose is to be determined.

Concept introduction: The aldehyde carbonyl group and ketone carbonyl group reduces to alcohol on reaction with NaBH4. The C=O group changes to C−OH on reduction.

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Predict the products obtained when d-galactose reacts with each reagent. NaOH, H2O

N-NHPH CHO CH2OH H- C=N-NHPH Но- -H- 3 equiv Но- -H- 3 equiv Но- PHNHNH2 PHNHNH, H- H- OH H- -O- H- H- -HO- H- -HO- ČH2OH ČH2OH ČH2OH D-glucose osazone D-fructose + NH3 + PHNH2 + 2 H20 The final step in the formation of the osazone from glucose is the reaction of the keto imine with 2 equivalents of phenylhydrazine to yield the osazone plus ammonia. This reaction involves the following intermediate steps: 1. Addition of phenylhydrazine to the imine and proton transfer to yield intermediate 1; 2. Elimination of ammonia to yield phenylhydrazone 2; 3. Addition of phenylhydrazine to the ketone to yield tetrahedral intermediate 3; 4. Proton transfer yields carbinolamine 4; 5. Elimination of water yields the final product osazone. Write out the mechanism on a separate sh of paper and then draw the structure of tetrahedral intermediate 3. NH НО- -H H- -ОН H- -ОН ОН Glucose keto imine Previous Ne

Predict the products obtained when d-galactose reacts with each reagent.(a) Br2 and H2O (b) NaOH, H2O (c) CH3OH, H +

Answer 2

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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 26.9, Problem 20P

Interpretation Introduction

Interpretation: The structure of 2-ketohexose is to be determined.

Concept introduction: The aldehyde carbonyl group and ketone carbonyl group reduces to alcohol on reaction with NaBH4. The C=O group changes to C−OH on reduction.

Expert Solution & Answer

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Answer 3

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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 26.9, Problem 20P

Interpretation Introduction

Interpretation: The structure of 2-ketohexose is to be determined.

Concept introduction: The aldehyde carbonyl group and ketone carbonyl group reduces to alcohol on reaction with NaBH4. The C=O group changes to C−OH on reduction.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

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 26.9, Problem 20P

Interpretation Introduction

Interpretation: The structure of 2-ketohexose is to be determined.

Concept introduction: The aldehyde carbonyl group and ketone carbonyl group reduces to alcohol on reaction with NaBH4. The C=O group changes to C−OH on reduction.

Expert Solution & Answer

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Answer 5

Chapter 26.9, Problem 20P

Interpretation Introduction

Interpretation: The structure of 2-ketohexose is to be determined.

Concept introduction: The aldehyde carbonyl group and ketone carbonyl group reduces to alcohol on reaction with NaBH4. The C=O group changes to C−OH on reduction.

Answer 6

Chapter 26.9, Problem 20P

Interpretation Introduction

Interpretation: The structure of 2-ketohexose is to be determined.

Concept introduction: The aldehyde carbonyl group and ketone carbonyl group reduces to alcohol on reaction with NaBH4. The C=O group changes to C−OH on reduction.

Answer 7

Chapter 26.9, Problem 20P

Interpretation Introduction

Interpretation: The structure of 2-ketohexose is to be determined.

Concept introduction: The aldehyde carbonyl group and ketone carbonyl group reduces to alcohol on reaction with NaBH4. The C=O group changes to C−OH on reduction.

Answer 8

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Answer 11

Ch. 26.2 - Prob. 1P Ch. 26.2 - Prob. 2P Ch. 26.2 - Label each stereogenic center as R or S. a. b. c....Ch. 26.2 - Convert the ball-and-stick model to a Fischer...Ch. 26.2 - Prob. 5P Ch. 26.2 - Prob. 6P Ch. 26.3 - Prob. 7P Ch. 26.3 - Prob. 8P Ch. 26.4 - Prob. 9P Ch. 26.4 - Prob. 10P

The structure of 2 -ketohexose is to be determined. Concept introduction: The aldehyde carbonyl group and ketone carbonyl group reduces to alcohol on reaction with NaBH 4 . The C = O group changes to C − OH on reduction.

Solution Summary: The author explains that the structure of 2 -ketohexose is shown in Figure 2.

Concept explainers

Interpretation: The structure of 2-ketohexose is to be determined.

Concept introduction: The aldehyde carbonyl group and ketone carbonyl group reduces to alcohol on reaction with NaBH4. The C=O group changes to C−OH on reduction.

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Chapter 26 Solutions

The structure of 2 -ketohexose is to be determined. Concept introduction: The aldehyde carbonyl group and ketone carbonyl group reduces to alcohol on reaction with NaBH 4 . The C = O group changes to C − OH on reduction.

Solution Summary: The author explains that the structure of 2 -ketohexose is shown in Figure 2.

Concept explainers

Interpretation: The structure of 2-ketohexose is to be determined. Concept introduction: The aldehyde carbonyl group and ketone carbonyl group reduces to alcohol on reaction with NaBH4. The C=O group changes to C−OH on reduction.

Want to see the full answer?

Chapter 26 Solutions

Interpretation: The structure of 2-ketohexose is to be determined.

Concept introduction: The aldehyde carbonyl group and ketone carbonyl group reduces to alcohol on reaction with NaBH4. The C=O group changes to C−OH on reduction.