The mechanism for the formation of o-(hydroxymethyl)benzoic acid when o-phthalaldehyde is treated with a base is to be proposed. Concept introduction: The Cannizzaro reaction takes place by nucleophilic addition of OH - to an aldehyde to give a tetrahedral intermediate, which expels a hydride ion and is thereby oxidized. A second aldehyde group, either within the same intermediate or from another molecule, accepts the hydride ion and thus gets reduced to an alcohol. To propose: The mechanism for the formation of o-(hydroxymethyl) benzoic acid when o-phthalaldehyde is treated with a base.

Question

Draw the two electrophiles for this reaction.

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 19.12, Problem 18P

Interpretation Introduction

Interpretation:

The mechanism for the formation of o-(hydroxymethyl)benzoic acid when o-phthalaldehyde is treated with a base is to be proposed.

Concept introduction:

The Cannizzaro reaction takes place by nucleophilic addition of OH^- to an aldehyde to give a tetrahedral intermediate, which expels a hydride ion and is thereby oxidized. A second aldehyde group, either within the same intermediate or from another molecule, accepts the hydride ion and thus gets reduced to an alcohol.

To propose:

The mechanism for the formation of o-(hydroxymethyl) benzoic acid when o-phthalaldehyde is treated with a base.

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Can you draw the mechanism for the synthesis of cyclohexene from cyclohexanol through an acid-catalyzed dehydration reaction. Where Phosphoric acid donates a proton ((H^+)) to the hydroxyl group of cyclohexanol, forming a protonated cyclohexanol intermediate. • The protonated cyclohexanol undergoes dehydration, leading to the removal of a water molecule and the formation of cyclohexene. • The released proton combines with water to form hydronium ion (H3O+), regenerating the catalyst. The mechanism should illustrate the acid-catalyzed dehydration process, where phosphoric acid facilitates the removal of water from cyclohexanol, resulting in the formation of cyclohexene.

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 19.12, Problem 18P

Interpretation Introduction

Interpretation:

The mechanism for the formation of o-(hydroxymethyl)benzoic acid when o-phthalaldehyde is treated with a base is to be proposed.

Concept introduction:

The Cannizzaro reaction takes place by nucleophilic addition of OH^- to an aldehyde to give a tetrahedral intermediate, which expels a hydride ion and is thereby oxidized. A second aldehyde group, either within the same intermediate or from another molecule, accepts the hydride ion and thus gets reduced to an alcohol.

To propose:

The mechanism for the formation of o-(hydroxymethyl) benzoic acid when o-phthalaldehyde is treated with a base.

Expert Solution & Answer

Trending nowThis is a popular solution!

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 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 19.12, Problem 18P

Interpretation Introduction

Interpretation:

The mechanism for the formation of o-(hydroxymethyl)benzoic acid when o-phthalaldehyde is treated with a base is to be proposed.

Concept introduction:

The Cannizzaro reaction takes place by nucleophilic addition of OH^- to an aldehyde to give a tetrahedral intermediate, which expels a hydride ion and is thereby oxidized. A second aldehyde group, either within the same intermediate or from another molecule, accepts the hydride ion and thus gets reduced to an alcohol.

To propose:

The mechanism for the formation of o-(hydroxymethyl) benzoic acid when o-phthalaldehyde is treated with a base.

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 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 19.12, Problem 18P

Interpretation Introduction