Using the given transformation, the structural formulae for isoborneol and camphor are to be deduced. Concept introduction: The secondary alcohols on oxidation with strong oxidizing agent chromic acid form ketone . The reduction of the asymmetric ketone gives isomers of the secondary alcohol. The borneol and isoborneol are stereoisomers.

Question

4. Compound A has the formula C 8H 8. It reacts rapidly with KMnO 4 to give CO 2 and a carboxylic acid, B (C 7H 6O 2), but reacts with only 1 molar equivalent of H 2 on catalytic hydrogenation over a palladium catalyst. On hydrogenation under conditions that reduce aromatic rings, 4, equivalents of H 2 are taken up and hydrocarbon C (C 8H 16) is produced. What are the structures of A, B, and C.

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 25.9, Problem 11P

Interpretation Introduction

Interpretation:

Using the given transformation, the structural formulae for isoborneol and camphor are to be deduced.

Concept introduction:

The secondary alcohols on oxidation with strong oxidizing agent chromic acid form ketone.

The reduction of the asymmetric ketone gives isomers of the secondary alcohol.

The borneol and isoborneol are stereoisomers.

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4. Compound A has the formula C 8H 8. It reacts rapidly with KMnO 4 to give CO 2 and a carboxylic acid, B (C 7H 6O 2), but reacts with only 1 molar equivalent of H 2 on catalytic hydrogenation over a palladium catalyst. On hydrogenation under conditions that reduce aromatic rings, 4, equivalents of H 2 are taken up and hydrocarbon C (C 8H 16) is produced. What are the structures of A, B, and C.

Which of the following statements is true? a) PCC oxidizes alkanes to alcohols b) PCC and PDC are environmentally-friendly reagents c) The Swern oxidation uses a combination of oxalyl chloride and PDC d) Swern oxidations are difficult to perform because they require very low reaction temperatures and need to be performed in the absence of water and air e) PCC and PDC are derived from manganese metal

Imagine that phenol (“hydroxybenzene”) and nitrobenzene are reacted (in separate beakers) with a hot solution containing both concentrated sulfuric acid and concentrated nitric acid. A) When chlorobenzene reacts with a hot solution of sulfuric and nitric acids, an interesting result occurs: the reaction is slower than the reaction of the solution with benzene – which is similar to the result of the reaction of the solution with nitrobenzene – but it generates products with the same substitution pattern seen in the reaction of the solution with phenol. Explain why chlorobenzene has this curious reactivity.

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 25.9, Problem 11P

Interpretation Introduction

Interpretation:

Using the given transformation, the structural formulae for isoborneol and camphor are to be deduced.

Concept introduction:

The secondary alcohols on oxidation with strong oxidizing agent chromic acid form ketone.

The reduction of the asymmetric ketone gives isomers of the secondary alcohol.

The borneol and isoborneol are stereoisomers.

Expert Solution & Answer

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See solution

Check out sample textbook 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 25.9, Problem 11P

Interpretation Introduction

Interpretation:

Using the given transformation, the structural formulae for isoborneol and camphor are to be deduced.

Concept introduction:

The secondary alcohols on oxidation with strong oxidizing agent chromic acid form ketone.

The reduction of the asymmetric ketone gives isomers of the secondary alcohol.

The borneol and isoborneol are stereoisomers.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook 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 25.9, Problem 11P

Interpretation Introduction