(a) Interpretation: The hydroboration-oxidation and mercuric-ion catalysed hydration reaction for cyclohexylacetylene are to be compared. Concept introduction: Hydroboration-oxidation reaction of an alkyne is the reaction in which an alkyne reacts with borane in presence of a peroxide to yield an enol which tautomerises to a corresponding aldehyde or a ketone . The reaction occurs by Anti-Markovnikov’s rule. An alkyne can be converted into an aldehyde or a ketone by mercuric-ion catalysed hydration reaction. After the protonation of the alkynyl carbon, the water attacks as the nucleophile and an enol is formed. Enol is unstable and converts into a stable aldehyde or ketone.

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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 14, Problem 14.12P

Interpretation Introduction

(a)

Interpretation:

The hydroboration-oxidation and mercuric-ion catalysed hydration reaction for cyclohexylacetylene are to be compared.

Concept introduction:

Hydroboration-oxidation reaction of an alkyne is the reaction in which an alkyne reacts with borane in presence of a peroxide to yield an enol which tautomerises to a corresponding aldehyde or a ketone. The reaction occurs by Anti-Markovnikov’s rule. An alkyne can be converted into an aldehyde or a ketone by mercuric-ion catalysed hydration reaction. After the protonation of the alkynyl carbon, the water attacks as the nucleophile and an enol is formed. Enol is unstable and converts into a stable aldehyde or ketone.

Interpretation Introduction

(b)

Interpretation:

The hydroboration-oxidation and mercuric-ion catalysed hydration reaction for 2-butyne are to be compared.

Concept introduction:

Hydroboration-oxidation reaction is the reaction in which an alkene reacts with borane in presence of a peroxide to yield primary alcohol. The reaction occurs by Anti-Markovnikov’s rule. An alkyne can be converted into an aldehyde or a ketone by mercuric-ion catalysed hydration reaction. After the protonation of the alkynyl carbon, the water attacks as the nucleophile and an enol is formed. Enol is unstable and converts into a stable aldehyde or ketone.

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Transmitance 3. Which one of the following compounds corresponds to this IR spectrum? Point out the absorption band(s) that helped you decide. OH H3C OH H₂C CH3 H3C CH3 H3C INFRARED SPECTRUM 0.8- 0.6 0.4- 0.2 3000 2000 1000 Wavenumber (cm-1) 4. Consider this compound: H3C On the structure above, label the different types of H's as A, B, C, etc. In table form, list the labeled signals, and for each one state the number of hydrogens, their shifts, and the splitting you would observe for these hydrogens in the ¹H NMR spectrum. Label # of hydrogens splitting Shift (2)

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 14, Problem 14.12P

Interpretation Introduction

(a)

Interpretation:

The hydroboration-oxidation and mercuric-ion catalysed hydration reaction for cyclohexylacetylene are to be compared.

Concept introduction:

Hydroboration-oxidation reaction of an alkyne is the reaction in which an alkyne reacts with borane in presence of a peroxide to yield an enol which tautomerises to a corresponding aldehyde or a ketone. The reaction occurs by Anti-Markovnikov’s rule. An alkyne can be converted into an aldehyde or a ketone by mercuric-ion catalysed hydration reaction. After the protonation of the alkynyl carbon, the water attacks as the nucleophile and an enol is formed. Enol is unstable and converts into a stable aldehyde or ketone.

Interpretation Introduction

(b)

Interpretation:

The hydroboration-oxidation and mercuric-ion catalysed hydration reaction for 2-butyne are to be compared.

Concept introduction:

Hydroboration-oxidation reaction is the reaction in which an alkene reacts with borane in presence of a peroxide to yield primary alcohol. The reaction occurs by Anti-Markovnikov’s rule. An alkyne can be converted into an aldehyde or a ketone by mercuric-ion catalysed hydration reaction. After the protonation of the alkynyl carbon, the water attacks as the nucleophile and an enol is formed. Enol is unstable and converts into a stable aldehyde or ketone.

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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 14, Problem 14.12P

Interpretation Introduction

(a)

Interpretation:

The hydroboration-oxidation and mercuric-ion catalysed hydration reaction for cyclohexylacetylene are to be compared.

Concept introduction:

Hydroboration-oxidation reaction of an alkyne is the reaction in which an alkyne reacts with borane in presence of a peroxide to yield an enol which tautomerises to a corresponding aldehyde or a ketone. The reaction occurs by Anti-Markovnikov’s rule. An alkyne can be converted into an aldehyde or a ketone by mercuric-ion catalysed hydration reaction. After the protonation of the alkynyl carbon, the water attacks as the nucleophile and an enol is formed. Enol is unstable and converts into a stable aldehyde or ketone.

Interpretation Introduction

(b)

Interpretation:

The hydroboration-oxidation and mercuric-ion catalysed hydration reaction for 2-butyne are to be compared.

Concept introduction:

Hydroboration-oxidation reaction is the reaction in which an alkene reacts with borane in presence of a peroxide to yield primary alcohol. The reaction occurs by Anti-Markovnikov’s rule. An alkyne can be converted into an aldehyde or a ketone by mercuric-ion catalysed hydration reaction. After the protonation of the alkynyl carbon, the water attacks as the nucleophile and an enol is formed. Enol is unstable and converts into a stable aldehyde or ketone.

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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 14, Problem 14.12P

Interpretation Introduction

(a)

Interpretation:

The hydroboration-oxidation and mercuric-ion catalysed hydration reaction for cyclohexylacetylene are to be compared.

Concept introduction:

Hydroboration-oxidation reaction of an alkyne is the reaction in which an alkyne reacts with borane in presence of a peroxide to yield an enol which tautomerises to a corresponding aldehyde or a ketone. The reaction occurs by Anti-Markovnikov’s rule. An alkyne can be converted into an aldehyde or a ketone by mercuric-ion catalysed hydration reaction. After the protonation of the alkynyl carbon, the water attacks as the nucleophile and an enol is formed. Enol is unstable and converts into a stable aldehyde or ketone.

Interpretation Introduction

(b)

Interpretation:

The hydroboration-oxidation and mercuric-ion catalysed hydration reaction for 2-butyne are to be compared.

Concept introduction:

Hydroboration-oxidation reaction is the reaction in which an alkene reacts with borane in presence of a peroxide to yield primary alcohol. The reaction occurs by Anti-Markovnikov’s rule. An alkyne can be converted into an aldehyde or a ketone by mercuric-ion catalysed hydration reaction. After the protonation of the alkynyl carbon, the water attacks as the nucleophile and an enol is formed. Enol is unstable and converts into a stable aldehyde or ketone.

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Answer 5

Chapter 14, Problem 14.12P

Interpretation Introduction

(a)

Interpretation:

The hydroboration-oxidation and mercuric-ion catalysed hydration reaction for cyclohexylacetylene are to be compared.

Concept introduction:

Hydroboration-oxidation reaction of an alkyne is the reaction in which an alkyne reacts with borane in presence of a peroxide to yield an enol which tautomerises to a corresponding aldehyde or a ketone. The reaction occurs by Anti-Markovnikov’s rule. An alkyne can be converted into an aldehyde or a ketone by mercuric-ion catalysed hydration reaction. After the protonation of the alkynyl carbon, the water attacks as the nucleophile and an enol is formed. Enol is unstable and converts into a stable aldehyde or ketone.

Interpretation Introduction

(b)

Interpretation:

The hydroboration-oxidation and mercuric-ion catalysed hydration reaction for 2-butyne are to be compared.

Concept introduction:

Hydroboration-oxidation reaction is the reaction in which an alkene reacts with borane in presence of a peroxide to yield primary alcohol. The reaction occurs by Anti-Markovnikov’s rule. An alkyne can be converted into an aldehyde or a ketone by mercuric-ion catalysed hydration reaction. After the protonation of the alkynyl carbon, the water attacks as the nucleophile and an enol is formed. Enol is unstable and converts into a stable aldehyde or ketone.

Answer 6

Chapter 14, Problem 14.12P

Interpretation Introduction

(a)

Interpretation:

The hydroboration-oxidation and mercuric-ion catalysed hydration reaction for cyclohexylacetylene are to be compared.

Concept introduction:

Hydroboration-oxidation reaction of an alkyne is the reaction in which an alkyne reacts with borane in presence of a peroxide to yield an enol which tautomerises to a corresponding aldehyde or a ketone. The reaction occurs by Anti-Markovnikov’s rule. An alkyne can be converted into an aldehyde or a ketone by mercuric-ion catalysed hydration reaction. After the protonation of the alkynyl carbon, the water attacks as the nucleophile and an enol is formed. Enol is unstable and converts into a stable aldehyde or ketone.

Answer 7

Chapter 14, Problem 14.12P

Interpretation Introduction

(a)

Interpretation:

The hydroboration-oxidation and mercuric-ion catalysed hydration reaction for cyclohexylacetylene are to be compared.

Concept introduction:

Hydroboration-oxidation reaction of an alkyne is the reaction in which an alkyne reacts with borane in presence of a peroxide to yield an enol which tautomerises to a corresponding aldehyde or a ketone. The reaction occurs by Anti-Markovnikov’s rule. An alkyne can be converted into an aldehyde or a ketone by mercuric-ion catalysed hydration reaction. After the protonation of the alkynyl carbon, the water attacks as the nucleophile and an enol is formed. Enol is unstable and converts into a stable aldehyde or ketone.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The hydroboration-oxidation and mercuric-ion catalysed hydration reaction for 2-butyne are to be compared.

Concept introduction:

Hydroboration-oxidation reaction is the reaction in which an alkene reacts with borane in presence of a peroxide to yield primary alcohol. The reaction occurs by Anti-Markovnikov’s rule. An alkyne can be converted into an aldehyde or a ketone by mercuric-ion catalysed hydration reaction. After the protonation of the alkynyl carbon, the water attacks as the nucleophile and an enol is formed. Enol is unstable and converts into a stable aldehyde or ketone.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The hydroboration-oxidation and mercuric-ion catalysed hydration reaction for 2-butyne are to be compared.

Concept introduction:

Hydroboration-oxidation reaction is the reaction in which an alkene reacts with borane in presence of a peroxide to yield primary alcohol. The reaction occurs by Anti-Markovnikov’s rule. An alkyne can be converted into an aldehyde or a ketone by mercuric-ion catalysed hydration reaction. After the protonation of the alkynyl carbon, the water attacks as the nucleophile and an enol is formed. Enol is unstable and converts into a stable aldehyde or ketone.

Answer 10

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Answer 13

Ch. 14 - Prob. 14.1P Ch. 14 - Prob. 14.2P Ch. 14 - Prob. 14.3P Ch. 14 - Prob. 14.4P Ch. 14 - Prob. 14.5P Ch. 14 - Prob. 14.6P Ch. 14 - Prob. 14.7P Ch. 14 - Prob. 14.8P Ch. 14 - Prob. 14.9P Ch. 14 - Prob. 14.10P

Solution Summary: The author explains the hydroboration-oxidation and mercuric-ion catalysed hydration reactions of cyclohexylacetylene.

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