The product formed by the treatment of compound A with LDA followed by CH 3 CH 2 I is to be predicted. The multistep method for the conversion of A to B is to be devised. Concept introduction: Lithium diisopropylamide (LDA) is a sterically hindered strong base. In an unsymmetrical ketone, it abstracts hydrogen from least substituted carbon to form kinetic product. Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively. The first step is abstraction of proton and second step is attack of electrophile to form alkylated product.

Question

Want to see the full answer?

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 23, Problem 23.71P

Interpretation Introduction

Interpretation: The product formed by the treatment of compound A with LDA followed by CH3CH2I is to be predicted. The multistep method for the conversion of A to B is to be devised.

Concept introduction: Lithium diisopropylamide (LDA) is a sterically hindered strong base. In an unsymmetrical ketone, it abstracts hydrogen from least substituted carbon to form kinetic product.

Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively. The first step is abstraction of proton and second step is attack of electrophile to form alkylated product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

What is the NAME of the substrate product when benzene is first treated with HNO3 and H2SO4, and THEN treated (in a second step) with Br2, and FeCl3 (or FeBr3)?

Which compounds give an SN2 substitution reaction on treatment with alcoholic NaSH? (b) Which compounds give an E2 elimination reaction on treatment with alcoholic KOH? (c) Which compounds do not react under either of the previous reaction conditions?

17.36 Tamoxifen is an estrogen receptor modulator that is used in the treatment of breast cancer. Provide the missing reagents and the structure of compound A in the synthesis of tamoxifen. Page 707 HO (CH3)2N 1. C,H,MgBr 2. H + Compound A (CH3)2N Tamoxifen

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 23, Problem 23.71P

Interpretation Introduction

Interpretation: The product formed by the treatment of compound A with LDA followed by CH3CH2I is to be predicted. The multistep method for the conversion of A to B is to be devised.

Concept introduction: Lithium diisopropylamide (LDA) is a sterically hindered strong base. In an unsymmetrical ketone, it abstracts hydrogen from least substituted carbon to form kinetic product.

Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively. The first step is abstraction of proton and second step is attack of electrophile to form alkylated product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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 23, Problem 23.71P

Interpretation Introduction

Interpretation: The product formed by the treatment of compound A with LDA followed by CH3CH2I is to be predicted. The multistep method for the conversion of A to B is to be devised.

Concept introduction: Lithium diisopropylamide (LDA) is a sterically hindered strong base. In an unsymmetrical ketone, it abstracts hydrogen from least substituted carbon to form kinetic product.

Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively. The first step is abstraction of proton and second step is attack of electrophile to form alkylated product.

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 23, Problem 23.71P

Interpretation Introduction