The open-chain structure of each of the given compounds is to be determined. Concept introduction: Ketones react with diols to form acetals. This reaction is generally used as a protecting group of the carbonyl group in a reaction and then through hydrolysis, the respective carbonyl group can be generated back. Aldehydes react with diols to form hemiacetals. The reaction takes place in the presence of an acid. The formation of acetals and hemiacetals is a type of nucleophilic substitution reaction.

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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 18, Problem 36P

Interpretation Introduction

Interpretation:

The open-chain structure of each of the given compounds is to be determined.

Concept introduction:

Ketones react with diols to form acetals. This reaction is generally used as a protecting group of the carbonyl group in a reaction and then through hydrolysis, the respective carbonyl group can be generated back.

Aldehydes react with diols to form hemiacetals. The reaction takes place in the presence of an acid.

The formation of acetals and hemiacetals is a type of nucleophilic substitution reaction.

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Quinapril (trade name Accupril) is used to treat high blood pressure andcongestive heart failure. One step in the synthesis of quinapril involvesreaction of the racemic alkyl bromide A with a single enantiomer of theamino ester B. Given the structure of quinapril, which one of these two products isneeded to synthesize the drug?

Compound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide (HC≡CNa) )with 1,12-dibromododecane. On treatment of compound A with sodium amide, it was converted to compound B (C14H24). Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26), while hydrogenation over platinum gave compound D (C14H28). Sodium-ammonia reduction of compound B gave compound E (C14H26). Both C and E yielded O═CH(CH2)12CH═O on ozonolysis. Assign structures to compound A through E so as to be consistent with the observed transformations.

Compound A is an optically active alcohol. Treatment with chromic acid converts A intoa ketone, B. In a separate reaction, A is treated with PBr3, converting A into compound C.Compound C is purified, and then it is allowed to react with magnesium in ether to give aGrignard reagent, D. Compound B is added to the resulting solution of the Grignard reagent. After hydrolysis of the initialproduct (E), this solution is found to contain 3,4-dimethylhexan-3-ol. Propose structures for compounds A, B, C, D, and E.

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 18, Problem 36P

Interpretation Introduction

Interpretation:

The open-chain structure of each of the given compounds is to be determined.

Concept introduction:

Ketones react with diols to form acetals. This reaction is generally used as a protecting group of the carbonyl group in a reaction and then through hydrolysis, the respective carbonyl group can be generated back.

Aldehydes react with diols to form hemiacetals. The reaction takes place in the presence of an acid.

The formation of acetals and hemiacetals is a type of nucleophilic substitution reaction.

Expert Solution & Answer

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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 18, Problem 36P

Interpretation Introduction

Interpretation:

The open-chain structure of each of the given compounds is to be determined.

Concept introduction:

Ketones react with diols to form acetals. This reaction is generally used as a protecting group of the carbonyl group in a reaction and then through hydrolysis, the respective carbonyl group can be generated back.

Aldehydes react with diols to form hemiacetals. The reaction takes place in the presence of an acid.

The formation of acetals and hemiacetals is a type of nucleophilic substitution reaction.

Expert Solution & Answer

Want to see the full answer?

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 18, Problem 36P

Interpretation Introduction