The carbonyl group of each of the eight D-aldohexoses is reduced with NaBH 4 and protonated with HCl . Among the reduced and protonated products, the one that is optically active has to be found. Concept Introduction: Reduction Reaction: The aldehyde and ketones in the presence of strong reducing reagent (like N a B H 4 , L i A l H 4 , N a / N H 3 etc.,) the carbonyl compound reduced saturated alkanes , alcohols. If the keto group involves in the reduction process of N a B H 4 , this carbonyl group reducing to give the different type alcohols. Example: Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule. First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation. Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product. Optical activity: molecule or substances that can rotate the plane-polarized light are said to be optically active. Meso compound are optically inactive, because meso compound is a stereoisomer with an identical or superimposable mirror image. Plane of symmetry: When structure of the compound can be cut into two equal halves along the plane. Then such plane is called as plane of symmetry. The stereoisomerism is the arrangement of atoms in molecules whose connectivity remains the same but their arrangement in different in each isomer.

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Answer 1

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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 16, Problem 20P

Interpretation Introduction

Interpretation:

The carbonyl group of each of the eight D-aldohexoses is reduced with NaBH4 and protonated with HCl. Among the reduced and protonated products, the one that is optically active has to be found.

Concept Introduction:

Reduction Reaction: The aldehyde and ketones in the presence of strong reducing reagent (like NaBH4, LiAlH4, Na/NH3 etc.,) the carbonyl compound reduced saturated alkanes, alcohols. If the keto group involves in the reduction process of NaBH4, this carbonyl group reducing to give the different type alcohols.

Example:

Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation.

Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product.

Optical activity: molecule or substances that can rotate the plane-polarized light are said to be optically active.

Meso compound are optically inactive, because meso compound is a stereoisomer with an identical or superimposable mirror image.

Plane of symmetry: When structure of the compound can be cut into two equal halves along the plane. Then such plane is called as plane of symmetry.

The stereoisomerism is the arrangement of atoms in molecules whose connectivity remains the same but their arrangement in different in each isomer.

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A graduate student was studying enzymatic reductions of cyclohexanones when she encountered some interesting chemistry. When she used an enzyme and NADPH to reduce the following ketone, she was surprised to find that the product was optically active. She carefully repurified the product so that no enzyme, NADPH, or other contaminants were present. Still, the product was optically active. Does the product have any asymmetric carbon atoms or other stereocenters?

One step in the gluconeogenesis pathway for the biosynthesis of glucose is the partial reduction of 3-phosphoglycerate to give glyceraldehyde 3-phosphate. The process occurs by phosphorylation with ATP to give 1,3-bisphosphoglycerate, reaction with a thiol group on the enzyme to give an enzyme-bound thioester, and reduction with NADH. -OPO3²- Enz-SH H-C-OH ATP CH₂OPO3²- 3-phosphoglycerate O 0-0--0 O ADP CH₂CH3 substitute for 1,3-bisphosphoglycerate C H-C-OH CH₂OPO3²- 1,3-bisphosphoglycerate O=C CH3-SH substitute for Enz-SH H H-C-OH | CH₂OPO3²- PO4³- O. S-Enz H-C-OH glyceraldehyde 3-phosphate Propose a structure for the first intermediates in the reaction of 1,3-bisphosphoglycerate with a thiol group on the enzyme to form an enzyme-bound thioester. Assume a basic group on the enzyme catalyzes the formation of this intermediate. To simplify the drawing process, substitute the structures below for the 1,3-bisphosphoglycerate and Enz-SH. CH₂OPO3²- (Enzyme-bound thioester) NADH/H* NAD*,…

The most stable conformation of the pyranose ring of most D-aldohexoses places the largest group, CH2OH, in the equatorial position. An exception to this is the aldohexose D-idose. Draw the two possible chair conformations of either the α or β anomer of D-idose. Explain why the more stable conformation has the CH2OH group in the axial position.

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 16, Problem 20P

Interpretation Introduction

Interpretation:

The carbonyl group of each of the eight D-aldohexoses is reduced with NaBH4 and protonated with HCl. Among the reduced and protonated products, the one that is optically active has to be found.

Concept Introduction:

Reduction Reaction: The aldehyde and ketones in the presence of strong reducing reagent (like NaBH4, LiAlH4, Na/NH3 etc.,) the carbonyl compound reduced saturated alkanes, alcohols. If the keto group involves in the reduction process of NaBH4, this carbonyl group reducing to give the different type alcohols.

Example:

Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation.

Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product.

Optical activity: molecule or substances that can rotate the plane-polarized light are said to be optically active.

Meso compound are optically inactive, because meso compound is a stereoisomer with an identical or superimposable mirror image.

Plane of symmetry: When structure of the compound can be cut into two equal halves along the plane. Then such plane is called as plane of symmetry.

The stereoisomerism is the arrangement of atoms in molecules whose connectivity remains the same but their arrangement in different in each isomer.

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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 16, Problem 20P

Interpretation Introduction

Interpretation:

The carbonyl group of each of the eight D-aldohexoses is reduced with NaBH4 and protonated with HCl. Among the reduced and protonated products, the one that is optically active has to be found.

Concept Introduction:

Reduction Reaction: The aldehyde and ketones in the presence of strong reducing reagent (like NaBH4, LiAlH4, Na/NH3 etc.,) the carbonyl compound reduced saturated alkanes, alcohols. If the keto group involves in the reduction process of NaBH4, this carbonyl group reducing to give the different type alcohols.

Example:

Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation.

Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product.

Optical activity: molecule or substances that can rotate the plane-polarized light are said to be optically active.

Meso compound are optically inactive, because meso compound is a stereoisomer with an identical or superimposable mirror image.

Plane of symmetry: When structure of the compound can be cut into two equal halves along the plane. Then such plane is called as plane of symmetry.

The stereoisomerism is the arrangement of atoms in molecules whose connectivity remains the same but their arrangement in different in each isomer.

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Check out a sample textbook solution

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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 16, Problem 20P

Interpretation Introduction