The observation, Grignard reaction of cyclohexanone with tert -butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D 3 O + is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it, is to be explained. Concept introduction: Grignard reagents add to the carbonyl group in aldehydes and ketones . The addition product when hydrolyzed with aqueous acids yields a secondary alcohol in the case of aldehydes other than formaldehyde and a secondary alcohol in the case of ketones. Ketones exist in acid catalyzed reversible equilibrium with their enol tatomers. To explain: The observation, Grignard reaction of cyclohexanone with tert -butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D 3 O + is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it.

Question

How many signals do you expect in the H NMR spectrum for this molecule? Br Br Write the answer below. Also, in each of the drawing areas below is a copy of the molecule, with Hs shown. In each copy, one of the H atoms is colored red. Highlight in red all other H atoms that would contribute to the same signal as the H already highlighted red. Note for advanced students: In this question, any multiplet is counted as one signal. Number of signals in the 'H NMR spectrum. For the molecule in the top drawing area, highlight in red any other H atoms that will contribute to the same signal as the H atom already highlighted red. If no other H atoms will contribute, check the box at right. No additional Hs to color in top molecule For the molecule in the bottom drawing area, highlight in red any other H atoms that will contribute to the same signal as the H atom already highlighted red. If no other H atoms will contribute, check the box at right. No additional Hs to color in bottom molecule

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 22.SE, Problem 61AP

Interpretation Introduction

Interpretation:

The observation, Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D₃O⁺ is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it, is to be explained.

Concept introduction:

Grignard reagents add to the carbonyl group in aldehydes and ketones. The addition product when hydrolyzed with aqueous acids yields a secondary alcohol in the case of aldehydes other than formaldehyde and a secondary alcohol in the case of ketones.

Ketones exist in acid catalyzed reversible equilibrium with their enol tatomers.

To explain:

The observation, Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D₃O⁺ is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it.

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How many signals do you expect in the H NMR spectrum for this molecule? Br Br Write the answer below. Also, in each of the drawing areas below is a copy of the molecule, with Hs shown. In each copy, one of the H atoms is colored red. Highlight in red all other H atoms that would contribute to the same signal as the H already highlighted red. Note for advanced students: In this question, any multiplet is counted as one signal. Number of signals in the 'H NMR spectrum. For the molecule in the top drawing area, highlight in red any other H atoms that will contribute to the same signal as the H atom already highlighted red. If no other H atoms will contribute, check the box at right. No additional Hs to color in top molecule For the molecule in the bottom drawing area, highlight in red any other H atoms that will contribute to the same signal as the H atom already highlighted red. If no other H atoms will contribute, check the box at right. No additional Hs to color in bottom molecule

In the drawing area below, draw the major products of this organic reaction: 1. NaOH ? 2. CH3Br If there are no major products, because nothing much will happen to the reactant under these reaction conditions, check the box under the drawing area instead. No reaction. Click and drag to start drawing a structure. ☐ : A ค

Predict the major products of the following organic reaction: NC Δ ? Some important Notes: • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. • Be sure to draw bonds carefully to show important geometric relationships between substituents. Note: if your answer contains a complicated ring structure, you must use one of the molecular fragment stamps (available in the menu at right) to enter the ring structure. You can add any substituents using the pencil tool in the usual way. Click and drag to start drawing a structure. Х а

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 22.SE, Problem 61AP

Interpretation Introduction

Interpretation:

The observation, Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D₃O⁺ is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it, is to be explained.

Concept introduction:

Grignard reagents add to the carbonyl group in aldehydes and ketones. The addition product when hydrolyzed with aqueous acids yields a secondary alcohol in the case of aldehydes other than formaldehyde and a secondary alcohol in the case of ketones.

Ketones exist in acid catalyzed reversible equilibrium with their enol tatomers.

To explain:

The observation, Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D₃O⁺ is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it.

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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 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 22.SE, Problem 61AP

Interpretation Introduction

Interpretation:

The observation, Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D₃O⁺ is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it, is to be explained.

Concept introduction:

Grignard reagents add to the carbonyl group in aldehydes and ketones. The addition product when hydrolyzed with aqueous acids yields a secondary alcohol in the case of aldehydes other than formaldehyde and a secondary alcohol in the case of ketones.

Ketones exist in acid catalyzed reversible equilibrium with their enol tatomers.

To explain:

The observation, Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D₃O⁺ is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it.

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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 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 22.SE, Problem 61AP

Interpretation Introduction