(a) Interpretation: Two different halo ketones that can form A by an intramolecular alkylation reaction is to be drawn. Concept introduction: 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. Lithium diisopropylamide (LDA) is a sterically hindered strong base. In an unsymmetrical ketone, it abstracts hydrogen from least substituted carbon to form kinetic product.

Question

Rate = k [I]1.7303[S2O82-]0.8502, Based on your rate, write down a mechanism consistent with your results and indicate which step is the rate determining step.

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 23.64P

Interpretation Introduction

(a)

Interpretation: Two different halo ketones that can form A by an intramolecular alkylation reaction is to be drawn.

Concept introduction: 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.

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

Interpretation Introduction

(b)

Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.

Concept introduction: 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.

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Rate = k [I]1.7303[S2O82-]0.8502, Based on your rate, write down a mechanism consistent with your results and indicate which step is the rate determining step.

36. Give the major product(s) of each of the following reactions. Aqueous work-up steps (when necessary) have been omitted. a. CH3CH=CHCH3 b. CH3CH2CH2CCH3 H,PO₂, H₂O, A (Hint: See Section 2-2.) 1. LIAIH. (CH,CH,),O 2. H', H₂O H NaBH, CH,CH₂OH d. Br LIAIH. (CH,CH,)₂O f. CH3 NaBH, CH,CH,OH (CH3)2CH H NaBH, CH,CH₂OH H

Predict the major products of this reaction: + H excess NaOH Δ ? Note that the second reactant is used in excess, that is, there is much more of the second reactant than the first. If there won't be any products, just check the box under the drawing area instead.

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 23.64P

Interpretation Introduction

(a)

Interpretation: Two different halo ketones that can form A by an intramolecular alkylation reaction is to be drawn.

Concept introduction: 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.

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

Interpretation Introduction

(b)

Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.

Concept introduction: 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.

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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 23, Problem 23.64P

Interpretation Introduction

(a)

Interpretation: Two different halo ketones that can form A by an intramolecular alkylation reaction is to be drawn.

Concept introduction: 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.

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

Interpretation Introduction

(b)

Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.

Concept introduction: 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.

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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 23, Problem 23.64P

Interpretation Introduction

(a)

Interpretation: Two different halo ketones that can form A by an intramolecular alkylation reaction is to be drawn.

Concept introduction: 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.

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

Interpretation Introduction

(b)

Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.

Concept introduction: 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.

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Answer 5

Chapter 23, Problem 23.64P

Interpretation Introduction

(a)

Interpretation: Two different halo ketones that can form A by an intramolecular alkylation reaction is to be drawn.

Concept introduction: 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.

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

Interpretation Introduction

(b)

Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.

Concept introduction: 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.

Answer 6

Chapter 23, Problem 23.64P

Interpretation Introduction

(a)

Interpretation: Two different halo ketones that can form A by an intramolecular alkylation reaction is to be drawn.

Concept introduction: 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.

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

Answer 7

Chapter 23, Problem 23.64P

Interpretation Introduction

(a)

Interpretation: Two different halo ketones that can form A by an intramolecular alkylation reaction is to be drawn.

Concept introduction: 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.

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

Answer 8

Interpretation Introduction

(b)

Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.

Concept introduction: 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.

Answer 9

Interpretation Introduction

(b)

Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.

Concept introduction: 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.

Answer 10

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Answer 21

Ch. 23 - Problem 23.1 Draw the enol or keto tautomer(s) of...Ch. 23 - Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.3P Ch. 23 - Prob. 23.4P Ch. 23 - Which CH bonds in the following molecules are...Ch. 23 - Prob. 23.6P Ch. 23 - Prob. 23.7P Ch. 23 - When ethyl acetoacetate (CH3COCH2CO2CH2CH3) is...Ch. 23 - Prob. 23.9P Ch. 23 - Prob. 23.10P

Solution Summary: The author explains that the synthesis of compound A from acetoacetic ester is to be devised.

Concept explainers

(b)

Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.

Concept introduction: 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.

Chapter 23 Solutions

Solution Summary: The author explains that the synthesis of compound A from acetoacetic ester is to be devised.

Concept explainers

(b) Interpretation: The synthesis of compound A from acetoacetic ester is to be devised. Concept introduction: 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.

Chapter 23 Solutions

(b)

Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.

Concept introduction: 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.