The mechanism of intramolecular aldol reaction involving heptanedial is to be drawn, along with the major product. Why this reaction is favored is to explained. Concept introduction: Intramolecular reactions are the ones in which the electron-rich and electron-poor sites are present within the same molecule. When ketones or aldehydes are treated with a strong base, they yield β -hydroxycarbonyl compounds via an aldol addition. Under these basic conditions, an enolate anion acts as a nucleophile. An intramolecular reaction is favored when it forms a five or six-membered ring. Intramolecular reactions involving the attack of an aldehyde C=O are favored over ones involving the attack of a ketone C=O . The first step is the formation of an enolate ion. The HO − reversibly deprotonates the alpha carbon to yield an enolate anion. In step two, the newly formed enolate anion, which serves as a nucleophile, attacks the carbonyl carbon present within the same molecule. The product of this step is an alkoxide ion, which is subsequently protonated in step 3.

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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 18.31P

Interpretation Introduction

Interpretation:

The mechanism of intramolecular aldol reaction involving heptanedial is to be drawn, along with the major product. Why this reaction is favored is to explained.

Concept introduction:

Intramolecular reactions are the ones in which the electron-rich and electron-poor sites are present within the same molecule. When ketones or aldehydes are treated with a strong base, they yield β-hydroxycarbonyl compounds via an aldol addition. Under these basic conditions, an enolate anion acts as a nucleophile. An intramolecular reaction is favored when it forms a five or six-membered ring. Intramolecular reactions involving the attack of an aldehyde C=O are favored over ones involving the attack of a ketone C=O.

The first step is the formation of an enolate ion. The HO− reversibly deprotonates the alpha carbon to yield an enolate anion. In step two, the newly formed enolate anion, which serves as a nucleophile, attacks the carbonyl carbon present within the same molecule. The product of this step is an alkoxide ion, which is subsequently protonated in step 3.

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CHEM2323 Problem 2-24 Tt O e: ל Predict the product(s) of the following acid/base reactions. Draw curved arrows to show the formation and breaking of bonds. If the bonds needed are not drawn out, you should redraw them. + BF3 (a) (b) HI + (c) OH -BF Problem 2-25 Use curved arrows and a proton (H+) to draw the protonated form of the following Lewis bases. Before starting, add all missing lone pairs. (a) (b) :0: (c) N 1 CHEM2323 PS CH02 Name:

CHEM2323 Problem 2-26 Tt O PS CH02 Name: Use the curved-arrow formalism to show how the electrons flow in the resonance form on the left to give the one on the right. (Draw all lone pairs first) (a) NH2 NH2 + (b) Problem 2-27 Double bonds can also act like Lewis bases, sharing their electrons with Lewis acids. Use curved arrows to show how each of the following double bonds will react with H-Cl and draw the resulting carbocation. (a) H2C=CH2 (b) (c) Problem 2-28 Identify the most electronegative element in each of the following molecules: (a) CH2FCI F Problem 2-29 (b) FCH2CH2CH2Br (c) HOCH2CH2NH2 (d) CH3OCH2Li F 0 0 Use the electronegativity table in Figure 2.3 to predict which bond in the following pairs is more polar and indicate the direction of bond polarity for each compound. (a) H3C-Cl or Cl-CI (b) H3C-H or H-CI (c) HO-CH3 or (CH3)3Si-CH3 (d) H3C-Li or Li-OH

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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 18.31P

Interpretation Introduction

Interpretation:

The mechanism of intramolecular aldol reaction involving heptanedial is to be drawn, along with the major product. Why this reaction is favored is to explained.

Concept introduction:

Intramolecular reactions are the ones in which the electron-rich and electron-poor sites are present within the same molecule. When ketones or aldehydes are treated with a strong base, they yield β-hydroxycarbonyl compounds via an aldol addition. Under these basic conditions, an enolate anion acts as a nucleophile. An intramolecular reaction is favored when it forms a five or six-membered ring. Intramolecular reactions involving the attack of an aldehyde C=O are favored over ones involving the attack of a ketone C=O.

The first step is the formation of an enolate ion. The HO− reversibly deprotonates the alpha carbon to yield an enolate anion. In step two, the newly formed enolate anion, which serves as a nucleophile, attacks the carbonyl carbon present within the same molecule. The product of this step is an alkoxide ion, which is subsequently protonated in step 3.

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Answer 3

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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 18.31P

Interpretation Introduction

Interpretation:

The mechanism of intramolecular aldol reaction involving heptanedial is to be drawn, along with the major product. Why this reaction is favored is to explained.

Concept introduction:

Intramolecular reactions are the ones in which the electron-rich and electron-poor sites are present within the same molecule. When ketones or aldehydes are treated with a strong base, they yield β-hydroxycarbonyl compounds via an aldol addition. Under these basic conditions, an enolate anion acts as a nucleophile. An intramolecular reaction is favored when it forms a five or six-membered ring. Intramolecular reactions involving the attack of an aldehyde C=O are favored over ones involving the attack of a ketone C=O.

The first step is the formation of an enolate ion. The HO− reversibly deprotonates the alpha carbon to yield an enolate anion. In step two, the newly formed enolate anion, which serves as a nucleophile, attacks the carbonyl carbon present within the same molecule. The product of this step is an alkoxide ion, which is subsequently protonated in step 3.

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Answer 4

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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 18.31P

Interpretation Introduction