a) Interpretation: Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone . The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn. Concept introduction: The enol picks up a proton from H 3 O + using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation ion then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone. To propose: A mechanism for the tautomerization reaction shown.

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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 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 9.SE, Problem 21MP

Interpretation Introduction

a)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation ion then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

Interpretation Introduction

b)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

Interpretation Introduction

c)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

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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 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 9.SE, Problem 21MP

Interpretation Introduction

a)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation ion then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

Interpretation Introduction

b)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

Interpretation Introduction

c)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

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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 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 9.SE, Problem 21MP

Interpretation Introduction

a)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation ion then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

Interpretation Introduction

b)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

Interpretation Introduction

c)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

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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 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 9.SE, Problem 21MP

Interpretation Introduction

a)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation ion then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

Interpretation Introduction

b)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

Interpretation Introduction

c)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

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Answer 5

Chapter 9.SE, Problem 21MP

Interpretation Introduction

a)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation ion then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

Interpretation Introduction

b)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

Interpretation Introduction

c)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

Answer 6

Chapter 9.SE, Problem 21MP

Interpretation Introduction

a)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation ion then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

Answer 7

Chapter 9.SE, Problem 21MP

Interpretation Introduction

a)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation ion then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

Answer 8

Interpretation Introduction

b)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

Answer 9

Interpretation Introduction

b)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

Answer 10

Interpretation Introduction

c)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

Answer 11

Interpretation Introduction

c)

Interpretation:

Given that the final step in the hydration of an alkyne under acidic conditions is the tautomerization of the enol intermediate to give the corresponding ketone. The mechanism involves protonation followed by deprotonation. Based on this information a mechanism for the tautomerization reaction shown is to be drawn.

Concept introduction:

The enol picks up a proton from H₃O⁺ using the unshared pair of electrons on oxygen and the Ï€ electrons in the double bond to yield a carbocation. The carbocation then loses a proton and the electrons in the O-H bond are moved towards the positively charged carbon to yield the ketone.

To propose:

A mechanism for the tautomerization reaction shown.

Answer 12

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Ch. 9.1 - Prob. 1P Ch. 9.1 - Prob. 2P Ch. 9.3 - What products would you expect from the following...Ch. 9.4 - Prob. 4P Ch. 9.4 - Prob. 5P Ch. 9.4 - Prob. 6P Ch. 9.4 - Prob. 7P Ch. 9.5 - Using any alkyne needed, how would you prepare the...Ch. 9.7 - The pKa of acetone, CH3COCH3, is 19.3. Which of...Ch. 9.8 - Prob. 10P

Chapter 9 Solutions