The stereochemistry of the pyruvate reduction shown is to be stated. Whether NADH lose its pro-R or pro-S hydrogen is to be stated. Whether the addition of hydrogen occurs to the Si face or Re face of pyruvate is also to be stated. Concept introduction: When an achiral molecule such as ketone , with a sp 2 hybridized carbon, is converted into a chiral molecule, which enantiomer will result depends on the face of the planar carbonyl carbon at which the reaction takes place. To distinguish the faces the descriptors Re and Si are used. The three groups attached to the carbonyl carbon are first arranged in the order of their priorities based on the sequence rules. The face in which the arrangement of the highest to second highest to third highest groups is clockwise is designated as Re face and if the arrangement in the face is anti-clockwise the face is called as Si face. In addition a compound with a sp 3 hybridized carbon also is said to be prochiral if by changing one of the attached groups it becomes a chiral centre. If the prochiral centre has two identical atoms, then that atom whose replacement leads to a R chirality centre is said to be pro R and that atom whose replacement leads to a S chirality centre is said to be pro S . To show: The stereochemistry of the pyruvate reduction to (s)-lactate shown and to state whether NADH lose its pro-R or pro-S hydrogen and whether the addition of hydrogen occurs to the Si face or Re face of pyruvate.

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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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 19.12, Problem 19P

Interpretation Introduction

Interpretation:

The stereochemistry of the pyruvate reduction shown is to be stated. Whether NADH lose its pro-R or pro-S hydrogen is to be stated. Whether the addition of hydrogen occurs to the Si face or Re face of pyruvate is also to be stated.

Concept introduction:

When an achiral molecule such as ketone, with a sp² hybridized carbon, is converted into a chiral molecule, which enantiomer will result depends on the face of the planar carbonyl carbon at which the reaction takes place. To distinguish the faces the descriptors Re and Si are used. The three groups attached to the carbonyl carbon are first arranged in the order of their priorities based on the sequence rules. The face in which the arrangement of the highest to second highest to third highest groups is clockwise is designated as Re face and if the arrangement in the face is anti-clockwise the face is called as Si face.

In addition a compound with a sp³ hybridized carbon also is said to be prochiral if by changing one of the attached groups it becomes a chiral centre. If the prochiral centre has two identical atoms, then that atom whose replacement leads to a R chirality centre is said to be pro R and that atom whose replacement leads to a S chirality centre is said to be pro S.

To show:

The stereochemistry of the pyruvate reduction to (s)-lactate shown and to state whether NADH lose its pro-R or pro-S hydrogen and whether the addition of hydrogen occurs to the Si face or Re face of pyruvate.

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Write what the products A, B, C, D, E, F, G, H, I, J and K are in the reactions below.

OH CO2 H3C CH3CHCH2CO, crotonate 3-hydroxybutyrate The hydration of crotonate to form 3-hydroxybutyrate occurs by the addition of -OH to the Re face of C. followed by protonation at the Si face of C2. Draw the product of the reaction, showing the stereochemistry. • Use the wedge/hash bond tools to indicate stercochemistry where it exists. • You do not have to explicitly draw H atoms. • If a group is achiral, do not use wedged or hashed bonds on it.

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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 19.12, Problem 19P

Interpretation Introduction

Interpretation:

The stereochemistry of the pyruvate reduction shown is to be stated. Whether NADH lose its pro-R or pro-S hydrogen is to be stated. Whether the addition of hydrogen occurs to the Si face or Re face of pyruvate is also to be stated.

Concept introduction:

When an achiral molecule such as ketone, with a sp² hybridized carbon, is converted into a chiral molecule, which enantiomer will result depends on the face of the planar carbonyl carbon at which the reaction takes place. To distinguish the faces the descriptors Re and Si are used. The three groups attached to the carbonyl carbon are first arranged in the order of their priorities based on the sequence rules. The face in which the arrangement of the highest to second highest to third highest groups is clockwise is designated as Re face and if the arrangement in the face is anti-clockwise the face is called as Si face.

In addition a compound with a sp³ hybridized carbon also is said to be prochiral if by changing one of the attached groups it becomes a chiral centre. If the prochiral centre has two identical atoms, then that atom whose replacement leads to a R chirality centre is said to be pro R and that atom whose replacement leads to a S chirality centre is said to be pro S.

To show:

The stereochemistry of the pyruvate reduction to (s)-lactate shown and to state whether NADH lose its pro-R or pro-S hydrogen and whether the addition of hydrogen occurs to the Si face or Re face of pyruvate.

Expert Solution & Answer

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Check out sample textbook solution

Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 19.12, Problem 19P

Interpretation Introduction

Interpretation:

The stereochemistry of the pyruvate reduction shown is to be stated. Whether NADH lose its pro-R or pro-S hydrogen is to be stated. Whether the addition of hydrogen occurs to the Si face or Re face of pyruvate is also to be stated.

Concept introduction:

When an achiral molecule such as ketone, with a sp² hybridized carbon, is converted into a chiral molecule, which enantiomer will result depends on the face of the planar carbonyl carbon at which the reaction takes place. To distinguish the faces the descriptors Re and Si are used. The three groups attached to the carbonyl carbon are first arranged in the order of their priorities based on the sequence rules. The face in which the arrangement of the highest to second highest to third highest groups is clockwise is designated as Re face and if the arrangement in the face is anti-clockwise the face is called as Si face.

In addition a compound with a sp³ hybridized carbon also is said to be prochiral if by changing one of the attached groups it becomes a chiral centre. If the prochiral centre has two identical atoms, then that atom whose replacement leads to a R chirality centre is said to be pro R and that atom whose replacement leads to a S chirality centre is said to be pro S.

To show:

The stereochemistry of the pyruvate reduction to (s)-lactate shown and to state whether NADH lose its pro-R or pro-S hydrogen and whether the addition of hydrogen occurs to the Si face or Re face of pyruvate.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 19.12, Problem 19P

Interpretation Introduction