The product formed in the reaction of 1-Hexanol with chromic acid has to be drawn. Concept Introduction: Oxidation of alcohols: Oxidation of primary alcohol gives an aldehyde or a carboxylic acid, depending on experimental conditions. Chromic acid Oxidation of an Alcohol: Step 1: Reaction of alcohol and chromic acid gives an alkyl chromate. No change in oxidation state of both Carbon and Chromium. Step 2: Take a proton away and simultaneously break bonds to give stable molecules or ions. Reaction of the alkyl chromate with a base (here water molecule) results in cleavage of a C-H bond, formation of the carbonyl groups, and reduction of Chromium (VI) to Chromium (IV).

Question

Compound A and compound B are in equilibrium. Write a stepwise mechanism from compound Ato compound B showing ALL intermediates. Use curved arrows to symbolize the flow of electrons to show how each of the intermediates and products are formed. Show all lone pairs and formal charges. Lastly, explain which compound (Aor B) will be in higher concentration.

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 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 10.8, Problem 10.11P

(a)

Interpretation Introduction

Interpretation:

The product formed in the reaction of 1-Hexanol with chromic acid has to be drawn.

Concept Introduction:

Oxidation of alcohols: Oxidation of primary alcohol gives an aldehyde or a carboxylic acid, depending on experimental conditions.

Chromic acid Oxidation of an Alcohol:

Step 1: Reaction of alcohol and chromic acid gives an alkyl chromate. No change in oxidation state of both Carbon and Chromium.

Step 2: Take a proton away and simultaneously break bonds to give stable molecules or ions. Reaction of the alkyl chromate with a base (here water molecule) results in cleavage of a C-H bond, formation of the carbonyl groups, and reduction of Chromium (VI) to Chromium (IV).

(b)

Interpretation Introduction

Interpretation:

The product formed in the reaction of 2-Hexanol with chromic acid has to be drawn.

Concept Introduction:

Oxidation of alcohols: Oxidation of primary alcohol gives an aldehyde or a carboxylic acid, depending on experimental conditions.

Chromic acid Oxidation of an Alcohol:

Step 1: Reaction of alcohol and chromic acid gives an alkyl chromate. No change in oxidation state of both Carbon and Chromium.

Step 2: Take a proton away and simultaneously break bonds to give stable molecules or ions. Reaction of the alkyl chromate with a base (here water molecule) results in cleavage of a C-H bond, formation of the carbonyl groups, and reduction of Chromium (VI) to Chromium (IV).

(c)

Interpretation Introduction

Interpretation:

The product formed in the reaction of Cyclohexanol with chromic acid has to be drawn.

Concept Introduction:

Oxidation of alcohols: Oxidation of primary alcohol gives an aldehyde or a carboxylic acid, depending on experimental conditions.

Chromic acid Oxidation of an Alcohol:

Step 1: Reaction of alcohol and chromic acid gives an alkyl chromate. No change in oxidation state of both Carbon and Chromium.

Step 2: Take a proton away and simultaneously break bonds to give stable molecules or ions. Reaction of the alkyl chromate with a base (here water molecule) results in cleavage of a C-H bond, formation of the carbonyl groups, and reduction of Chromium (VI) to Chromium (IV).

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Compound A and compound B are in equilibrium. Write a stepwise mechanism from compound Ato compound B showing ALL intermediates. Use curved arrows to symbolize the flow of electrons to show how each of the intermediates and products are formed. Show all lone pairs and formal charges. Lastly, explain which compound (Aor B) will be in higher concentration.

Write out the two-step sequence that converts benzene to each compound.

Draw and name all constitutionally isomeric alcohols with the molecular formula C4H10O

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 10.8, Problem 10.11P

(a)

Interpretation Introduction

Interpretation:

The product formed in the reaction of 1-Hexanol with chromic acid has to be drawn.

Concept Introduction:

Oxidation of alcohols: Oxidation of primary alcohol gives an aldehyde or a carboxylic acid, depending on experimental conditions.

Chromic acid Oxidation of an Alcohol:

Step 1: Reaction of alcohol and chromic acid gives an alkyl chromate. No change in oxidation state of both Carbon and Chromium.

Step 2: Take a proton away and simultaneously break bonds to give stable molecules or ions. Reaction of the alkyl chromate with a base (here water molecule) results in cleavage of a C-H bond, formation of the carbonyl groups, and reduction of Chromium (VI) to Chromium (IV).

(b)

Interpretation Introduction

Interpretation:

The product formed in the reaction of 2-Hexanol with chromic acid has to be drawn.

Concept Introduction:

Oxidation of alcohols: Oxidation of primary alcohol gives an aldehyde or a carboxylic acid, depending on experimental conditions.

Chromic acid Oxidation of an Alcohol:

Step 1: Reaction of alcohol and chromic acid gives an alkyl chromate. No change in oxidation state of both Carbon and Chromium.

Step 2: Take a proton away and simultaneously break bonds to give stable molecules or ions. Reaction of the alkyl chromate with a base (here water molecule) results in cleavage of a C-H bond, formation of the carbonyl groups, and reduction of Chromium (VI) to Chromium (IV).

(c)

Interpretation Introduction

Interpretation:

The product formed in the reaction of Cyclohexanol with chromic acid has to be drawn.

Concept Introduction:

Oxidation of alcohols: Oxidation of primary alcohol gives an aldehyde or a carboxylic acid, depending on experimental conditions.

Chromic acid Oxidation of an Alcohol:

Step 1: Reaction of alcohol and chromic acid gives an alkyl chromate. No change in oxidation state of both Carbon and Chromium.

Step 2: Take a proton away and simultaneously break bonds to give stable molecules or ions. Reaction of the alkyl chromate with a base (here water molecule) results in cleavage of a C-H bond, formation of the carbonyl groups, and reduction of Chromium (VI) to Chromium (IV).

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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 10.8, Problem 10.11P

(a)

Interpretation Introduction

Interpretation:

The product formed in the reaction of 1-Hexanol with chromic acid has to be drawn.

Concept Introduction:

Oxidation of alcohols: Oxidation of primary alcohol gives an aldehyde or a carboxylic acid, depending on experimental conditions.

Chromic acid Oxidation of an Alcohol:

Step 1: Reaction of alcohol and chromic acid gives an alkyl chromate. No change in oxidation state of both Carbon and Chromium.

Step 2: Take a proton away and simultaneously break bonds to give stable molecules or ions. Reaction of the alkyl chromate with a base (here water molecule) results in cleavage of a C-H bond, formation of the carbonyl groups, and reduction of Chromium (VI) to Chromium (IV).

(b)

Interpretation Introduction

Interpretation:

The product formed in the reaction of 2-Hexanol with chromic acid has to be drawn.

Concept Introduction:

Oxidation of alcohols: Oxidation of primary alcohol gives an aldehyde or a carboxylic acid, depending on experimental conditions.

Chromic acid Oxidation of an Alcohol:

Step 1: Reaction of alcohol and chromic acid gives an alkyl chromate. No change in oxidation state of both Carbon and Chromium.

Step 2: Take a proton away and simultaneously break bonds to give stable molecules or ions. Reaction of the alkyl chromate with a base (here water molecule) results in cleavage of a C-H bond, formation of the carbonyl groups, and reduction of Chromium (VI) to Chromium (IV).

(c)

Interpretation Introduction

Interpretation:

The product formed in the reaction of Cyclohexanol with chromic acid has to be drawn.

Concept Introduction:

Oxidation of alcohols: Oxidation of primary alcohol gives an aldehyde or a carboxylic acid, depending on experimental conditions.

Chromic acid Oxidation of an Alcohol:

Step 1: Reaction of alcohol and chromic acid gives an alkyl chromate. No change in oxidation state of both Carbon and Chromium.

Step 2: Take a proton away and simultaneously break bonds to give stable molecules or ions. Reaction of the alkyl chromate with a base (here water molecule) results in cleavage of a C-H bond, formation of the carbonyl groups, and reduction of Chromium (VI) to Chromium (IV).

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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 10.8, Problem 10.11P

(a)

Interpretation Introduction