Problem 21.18 The p K a ' s of ethyl acetoacetate and diethyl malonate are 11 and 13 , respectively. Write a structural formula for the most stable enolate of each using resonance to show the electron delocalization in each enolate. Interpretation: The structural formulas for the most stable enolate of ethyl acetoacetate and diethyl malonate is to be drawn and by considering the resonance the delocalization of electrons in each enolate is to be shown. Concept Introduction: > Enol refers to an intermediate structure that consists of an alkene group connected with a hydroxyl group at one end of its double bond. The removal of an alpha hydrogen atom from aldehyde or ketone forms enolate ion. > Resonance structure is a blend of two or more Lewis structures. Resonance structures are represented by a double headed arrow between the structures.

Question

18.65 Propose a plausible synthesis for the following trans- formation. CH3 CH3 CH3

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 21.6, Problem 18P

Interpretation Introduction

Problem 21.18

The pKa's of ethyl acetoacetate and diethyl malonate are 11 and 13, respectively. Write a structural formula for the most stable enolate of each using resonance to show the electron delocalization in each enolate.

Interpretation:

The structural formulas for the most stable enolate of ethyl acetoacetate and diethyl malonate is to be drawn and by considering the resonance the delocalization of electrons in each enolate is to be shown.

Concept Introduction:
>
Enol refers to an intermediate structure that consists of an alkene group connected with a hydroxyl group at one end of its double bond. The removal of an alpha hydrogen atom from aldehyde or ketone forms enolate ion.
>
Resonance structure is a blend of two or more Lewis structures. Resonance structures are represented by a double headed arrow between the structures.

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18.65 Propose a plausible synthesis for the following trans- formation. CH3 CH3 CH3

MeO 22.55 One potential synthesis of the anti-inflammatory and analgesic drug nabumetone is chloromethylation (Problem 22.48) of 2-methoxynaphthalene followed by an acetoacetic ester synthesis (Section 19.6). 5 3 6 CH₂O CI acetoacetic ester synthesis HC 7 MeO MeO 1 8 2-Methoxynaphthalene Nabumetone (a) Account for the regioselectivity of chloromethylation at carbon 6 rather than at carbon 5 or 7. (b) Show steps in the acetoacetic ester synthesis by which the synthesis of nabum- etone is completed.

One step in the synthesis of sitaglipitin (Problem 17.14, a drug used to treat type 2 diabetes) involves reaction of the mixed anhydride A with B to form C. Draw a stepwise mechanism for this reaction.

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 21.6, Problem 18P

Interpretation Introduction

Problem 21.18

The pKa's of ethyl acetoacetate and diethyl malonate are 11 and 13, respectively. Write a structural formula for the most stable enolate of each using resonance to show the electron delocalization in each enolate.

Interpretation:

The structural formulas for the most stable enolate of ethyl acetoacetate and diethyl malonate is to be drawn and by considering the resonance the delocalization of electrons in each enolate is to be shown.

Concept Introduction:
>
Enol refers to an intermediate structure that consists of an alkene group connected with a hydroxyl group at one end of its double bond. The removal of an alpha hydrogen atom from aldehyde or ketone forms enolate ion.
>
Resonance structure is a blend of two or more Lewis structures. Resonance structures are represented by a double headed arrow between the structures.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

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 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 21.6, Problem 18P

Interpretation Introduction

Problem 21.18

The pKa's of ethyl acetoacetate and diethyl malonate are 11 and 13, respectively. Write a structural formula for the most stable enolate of each using resonance to show the electron delocalization in each enolate.

Interpretation:

The structural formulas for the most stable enolate of ethyl acetoacetate and diethyl malonate is to be drawn and by considering the resonance the delocalization of electrons in each enolate is to be shown.

Concept Introduction:
>
Enol refers to an intermediate structure that consists of an alkene group connected with a hydroxyl group at one end of its double bond. The removal of an alpha hydrogen atom from aldehyde or ketone forms enolate ion.
>
Resonance structure is a blend of two or more Lewis structures. Resonance structures are represented by a double headed arrow between the structures.

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 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 21.6, Problem 18P

Interpretation Introduction