The mechanism should be drawn for the following transformation. Concept Introduction : Acetal formation : Acetal derivative of aldehyde and ketone are prepared by an acid catalyzed dehydration reaction with alcohols and diols. Acetals are germinal-diether derivatives of aldehydes or ketones . Ketone derivatives of acetal once called ketal , but in modern usages has dropped this name. Acid catalyzed formation reaction mechanism : Step-1 : An acid or base reaction, there is only a weak nucleophile we need to active the carbonyl group by protonating on O. Step2 : The nucleophilic O in the alcohol attacks the electrophilic C in the C=O, braking the pi-bond and giving the electrons to the positive O. Step-3: An acid or base reaction, deprotonation of alcoholic oxonium ion neutralizes the charging giving the hemi acetal. Step-4: In order for the –OH to leave we need to make it a better leaving group by protonation. Step 5: Using the electrons form the other O leaving group departure is facilitated. Step-6: The Nucleophilic O of the alcohol attacks the electrophilic C and the electrons of the pi- bonds to move to neutralize the charge on the positive O. Step-7 : Deprotonation of the alcoholic oxonium neutralizes the charge the charge on the positive O.

Question

Given a 1,3-dicarbonyl compound, state the (condensed) formula of the compound obtaineda) if I add hydroxylamine (NH2OH) to give an isooxazole.b) if I add thiosemicarbazide (NH2-CO-NH-NH2) to give an isothiazole.

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 20.5, Problem 8PTS

Interpretation Introduction

Interpretation: The mechanism should be drawn for the following transformation.

Concept Introduction:

Acetal formation: Acetal derivative of aldehyde and ketone are prepared by an acid catalyzed dehydration reaction with alcohols and diols.

Acetals are germinal-diether derivatives of aldehydes or ketones.

Ketone derivatives of acetal once called ketal, but in modern usages has dropped this name.

Acid catalyzed formation reaction mechanism:

Step-1: An acid or base reaction, there is only a weak nucleophile we need to active the carbonyl group by protonating on O.

Step2: The nucleophilic O in the alcohol attacks the electrophilic C in the C=O, braking the pi-bond and giving the electrons to the positive O.

Step-3: An acid or base reaction, deprotonation of alcoholic oxonium ion neutralizes the charging giving the hemi acetal.

Step-4: In order for the –OH to leave we need to make it a better leaving group by protonation.

Step 5: Using the electrons form the other O leaving group departure is facilitated.

Step-6: The Nucleophilic O of the alcohol attacks the electrophilic C and the electrons of the pi- bonds to move to neutralize the charge on the positive O.

Step-7: Deprotonation of the alcoholic oxonium neutralizes the charge the charge on the positive O.

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Given a 1,3-dicarbonyl compound, state the (condensed) formula of the compound obtaineda) if I add hydroxylamine (NH2OH) to give an isooxazole.b) if I add thiosemicarbazide (NH2-CO-NH-NH2) to give an isothiazole.

Complete the following acid-base reactions and predict the direction of equilibrium for each. Justify your prediction by citing pK values for the acid and conjugate acid in each equilibrium. (a) (b) NHs (c) O₂N NH NH OH H₁PO₁

23.34 Show how to convert each starting material into isobutylamine in good yield. ཅ ནད ཀྱི (b) Br OEt (c) (d) (e) (f) H

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 20.5, Problem 8PTS

Interpretation Introduction

Interpretation: The mechanism should be drawn for the following transformation.

Concept Introduction:

Acetal formation: Acetal derivative of aldehyde and ketone are prepared by an acid catalyzed dehydration reaction with alcohols and diols.

Acetals are germinal-diether derivatives of aldehydes or ketones.

Ketone derivatives of acetal once called ketal, but in modern usages has dropped this name.

Acid catalyzed formation reaction mechanism:

Step-1: An acid or base reaction, there is only a weak nucleophile we need to active the carbonyl group by protonating on O.

Step2: The nucleophilic O in the alcohol attacks the electrophilic C in the C=O, braking the pi-bond and giving the electrons to the positive O.

Step-3: An acid or base reaction, deprotonation of alcoholic oxonium ion neutralizes the charging giving the hemi acetal.

Step-4: In order for the –OH to leave we need to make it a better leaving group by protonation.

Step 5: Using the electrons form the other O leaving group departure is facilitated.

Step-6: The Nucleophilic O of the alcohol attacks the electrophilic C and the electrons of the pi- bonds to move to neutralize the charge on the positive O.

Step-7: Deprotonation of the alcoholic oxonium neutralizes the charge the charge on the positive O.

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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 20.5, Problem 8PTS

Interpretation Introduction

Interpretation: The mechanism should be drawn for the following transformation.

Concept Introduction:

Acetal formation: Acetal derivative of aldehyde and ketone are prepared by an acid catalyzed dehydration reaction with alcohols and diols.

Acetals are germinal-diether derivatives of aldehydes or ketones.

Ketone derivatives of acetal once called ketal, but in modern usages has dropped this name.

Acid catalyzed formation reaction mechanism:

Step-1: An acid or base reaction, there is only a weak nucleophile we need to active the carbonyl group by protonating on O.

Step2: The nucleophilic O in the alcohol attacks the electrophilic C in the C=O, braking the pi-bond and giving the electrons to the positive O.

Step-3: An acid or base reaction, deprotonation of alcoholic oxonium ion neutralizes the charging giving the hemi acetal.

Step-4: In order for the –OH to leave we need to make it a better leaving group by protonation.

Step 5: Using the electrons form the other O leaving group departure is facilitated.

Step-6: The Nucleophilic O of the alcohol attacks the electrophilic C and the electrons of the pi- bonds to move to neutralize the charge on the positive O.

Step-7: Deprotonation of the alcoholic oxonium neutralizes the charge the charge on the positive O.

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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 20.5, Problem 8PTS

Interpretation Introduction