The acid-catalyzed hydration of the internal alkyne leads to only a single adduct (in low yield). [DK1] The product of the given reaction is to be drawn. The reason the mixture of adducts is not produced is to be explained. Concept introduction: Acid-catalyzed hydration of an alkyne produces a ketone . Step 1 is the electrophilic addition of H + , which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. H + is added preferentially to the terminal C in Step 1 to give the more stable carbocation intermediate. Water must then add to the internal C atom in the second step. Deprotonation in Step 3 produces the uncharged OH group, which is attached to an alkene C. The product is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 11, Problem 11.41P

Interpretation Introduction

Interpretation:

The acid-catalyzed hydration of the internal alkyne leads to only a single adduct (in low yield). [DK1] The product of the given reaction is to be drawn. The reason the mixture of adducts is not produced is to be explained.

Concept introduction:

Acid-catalyzed hydration of an alkyne produces a ketone. Step 1 is the electrophilic addition of H+, which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. H+ is added preferentially to the terminal C in Step 1 to give the more stable carbocation intermediate. Water must then add to the internal C atom in the second step. Deprotonation in Step 3 produces the uncharged OH group, which is attached to an alkene C. The product is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

CH3O OH OH O hemiacetal O acetal O neither O 0 O hemiacetal acetal neither OH hemiacetal O acetal O neither CH2 O-CH2-CH3 CH3-C-OH O hemiacetal O acetal CH3-CH2-CH2-0-c-O-CH2-CH2-CH3 O neither HO-CH2 ? 000 Ar B

What would be the best choices for the missing reagents 1 and 3 in this synthesis? 1. PPh3 2 2. n-BuLi 3 Draw the missing reagents in the drawing area below. You can draw them in any arrangement you like. • Do not draw the missing reagent 2. If you draw 1 correctly, we'll know what it is. • Note: if one of your reagents needs to contain a halogen, use bromine. Explanation Check Click and drag to start drawing a structure.

Predict the products of this organic reaction: NaBH3CN + NH2 ? H+ Click and drag to start drawing a structure. ×

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 11, Problem 11.41P

Interpretation Introduction

Interpretation:

The acid-catalyzed hydration of the internal alkyne leads to only a single adduct (in low yield). [DK1] The product of the given reaction is to be drawn. The reason the mixture of adducts is not produced is to be explained.

Concept introduction:

Acid-catalyzed hydration of an alkyne produces a ketone. Step 1 is the electrophilic addition of H+, which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. H+ is added preferentially to the terminal C in Step 1 to give the more stable carbocation intermediate. Water must then add to the internal C atom in the second step. Deprotonation in Step 3 produces the uncharged OH group, which is attached to an alkene C. The product is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 11, Problem 11.41P

Interpretation Introduction

Interpretation:

The acid-catalyzed hydration of the internal alkyne leads to only a single adduct (in low yield). [DK1] The product of the given reaction is to be drawn. The reason the mixture of adducts is not produced is to be explained.

Concept introduction:

Acid-catalyzed hydration of an alkyne produces a ketone. Step 1 is the electrophilic addition of H+, which gives a resonance-stabilized vinylic carbocation intermediate. In step 2, water behaves as a nucleophile, attacking the positively charged C of that intermediate. H+ is added preferentially to the terminal C in Step 1 to give the more stable carbocation intermediate. Water must then add to the internal C atom in the second step. Deprotonation in Step 3 produces the uncharged OH group, which is attached to an alkene C. The product is an enol. Under acidic conditions, the enol rapidly tautomerizes to the more stable keto form.

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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 11, Problem 11.41P

Interpretation Introduction