a) Interpretation: The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided. Concept introduction: Ketones react with Grignard reagents to yield addition product which on acidification yield a tertiary alcohol a product. To identify: The products formed in the reaction given and to provide the mechanism of the reaction.

Question

2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled** Peak Chemical Shift (d) 5.7 1 Multiplicity multiplate .......... 5.04 double of doublet 2 4.98 double of doublet 3 4.05 doublet of quartet 4 5 LO 3.80 quartet 1.3 doublet 6 Peak Chemical Shift (d) Multiplicity

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.SE, Problem 31MP

Interpretation Introduction

a)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react with Grignard reagents to yield addition product which on acidification yield a tertiary alcohol a product.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

b)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes and ketones react with NaCN, HCN to yield cyanohydrins. It is a case of nucleophilic addition to the carbonyl group.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

c)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

NaBH₄ reduces aldehydes to primary alcohols and ketones to secondary alcohols. During the reaction the nucleophilic addition of hydrogen to the carbonyl group takes place.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

d)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes react with Grignard reagents to yield a secondary alcohol and with ketones to yield tertiary alcohols.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

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2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled** Peak Chemical Shift (d) 5.7 1 Multiplicity multiplate .......... 5.04 double of doublet 2 4.98 double of doublet 3 4.05 doublet of quartet 4 5 LO 3.80 quartet 1.3 doublet 6 Peak Chemical Shift (d) Multiplicity

Interpreting NMR spectra is a skill that often requires some amount of practice, which, in turn, necessitates access to a collection of NMR spectra. Beyond Labz Organic Synthesis and Organic Qualitative Analysis have spectral libraries containing over 700 1H NMR spectra. In this assignment, you will take advantage of this by first predicting the NMR spectra for two closely related compounds and then checking your predictions by looking up the actual spectra in the spectra library. After completing this assignment, you may wish to select other compounds for additional practice. 1. Write the IUPAC names for the following two structures: Question 2 Question 3 2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled**

11:14 ... worksheets.beyondlabz.com 3. To check your predictions, click this link for Interpreting NMR Spectra 1. You will see a list of all the - compounds in the spectra library in alphabetical order by IUPAC name. Hovering over a name in the list will show the structure on the chalkboard. The four buttons on the top of the Spectra tab in the tray are used to select the different spectroscopic techniques for the selected compound. Make sure the NMR button has been selected. 4. Scroll through the list of names to find the names for the two compounds you have been given and click on the name to display the NMR spectrum for each. In the NMR tables below, list the chemical shift, the splitting, and the number of hydrogens associated with each peak for each compound. Compare your answers to your predictions. **Not all slots must be filled** Peak Chemical Shift (d) Multiplicity 1 2 3 4 5

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.SE, Problem 31MP

Interpretation Introduction

a)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react with Grignard reagents to yield addition product which on acidification yield a tertiary alcohol a product.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

b)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes and ketones react with NaCN, HCN to yield cyanohydrins. It is a case of nucleophilic addition to the carbonyl group.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

c)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

NaBH₄ reduces aldehydes to primary alcohols and ketones to secondary alcohols. During the reaction the nucleophilic addition of hydrogen to the carbonyl group takes place.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

d)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes react with Grignard reagents to yield a secondary alcohol and with ketones to yield tertiary alcohols.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

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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 19.SE, Problem 31MP

Interpretation Introduction

a)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react with Grignard reagents to yield addition product which on acidification yield a tertiary alcohol a product.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

b)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes and ketones react with NaCN, HCN to yield cyanohydrins. It is a case of nucleophilic addition to the carbonyl group.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

c)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

NaBH₄ reduces aldehydes to primary alcohols and ketones to secondary alcohols. During the reaction the nucleophilic addition of hydrogen to the carbonyl group takes place.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

d)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes react with Grignard reagents to yield a secondary alcohol and with ketones to yield tertiary alcohols.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Expert Solution & Answer

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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 19.SE, Problem 31MP

Interpretation Introduction

a)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react with Grignard reagents to yield addition product which on acidification yield a tertiary alcohol a product.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

b)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes and ketones react with NaCN, HCN to yield cyanohydrins. It is a case of nucleophilic addition to the carbonyl group.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

c)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

NaBH₄ reduces aldehydes to primary alcohols and ketones to secondary alcohols. During the reaction the nucleophilic addition of hydrogen to the carbonyl group takes place.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

d)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes react with Grignard reagents to yield a secondary alcohol and with ketones to yield tertiary alcohols.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Expert Solution & Answer

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Check out sample textbook solution

Answer 5

Chapter 19.SE, Problem 31MP

Interpretation Introduction

a)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react with Grignard reagents to yield addition product which on acidification yield a tertiary alcohol a product.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

b)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes and ketones react with NaCN, HCN to yield cyanohydrins. It is a case of nucleophilic addition to the carbonyl group.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

c)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

NaBH₄ reduces aldehydes to primary alcohols and ketones to secondary alcohols. During the reaction the nucleophilic addition of hydrogen to the carbonyl group takes place.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Interpretation Introduction

d)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes react with Grignard reagents to yield a secondary alcohol and with ketones to yield tertiary alcohols.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Answer 6

Chapter 19.SE, Problem 31MP

Interpretation Introduction

a)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react with Grignard reagents to yield addition product which on acidification yield a tertiary alcohol a product.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Answer 7

Chapter 19.SE, Problem 31MP

Interpretation Introduction

a)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Ketones react with Grignard reagents to yield addition product which on acidification yield a tertiary alcohol a product.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Answer 8

Interpretation Introduction

b)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes and ketones react with NaCN, HCN to yield cyanohydrins. It is a case of nucleophilic addition to the carbonyl group.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Answer 9

Interpretation Introduction

b)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes and ketones react with NaCN, HCN to yield cyanohydrins. It is a case of nucleophilic addition to the carbonyl group.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Answer 10

Interpretation Introduction

c)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

NaBH₄ reduces aldehydes to primary alcohols and ketones to secondary alcohols. During the reaction the nucleophilic addition of hydrogen to the carbonyl group takes place.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Answer 11

Interpretation Introduction

c)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

NaBH₄ reduces aldehydes to primary alcohols and ketones to secondary alcohols. During the reaction the nucleophilic addition of hydrogen to the carbonyl group takes place.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Answer 12

Interpretation Introduction

d)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes react with Grignard reagents to yield a secondary alcohol and with ketones to yield tertiary alcohols.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Answer 13

Interpretation Introduction

d)

Interpretation:

The products formed in the reaction given are to be identified. The mechanism of the reaction also is to be provided.

Concept introduction:

Aldehydes react with Grignard reagents to yield a secondary alcohol and with ketones to yield tertiary alcohols.

To identify:

The products formed in the reaction given and to provide the mechanism of the reaction.

Answer 14

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Ch. 19.1 - Prob. 1P Ch. 19.1 - Draw structures corresponding to the following...Ch. 19.2 - Prob. 3P Ch. 19.2 - How would you carry out the following reactions?...Ch. 19.4 - Treatment of an aldehyde or ketone with cyanide...Ch. 19.4 - p-Nitrobenzaldehyde is more reactive toward...Ch. 19.5 - Prob. 7P Ch. 19.5 - The oxygen in water is primarily (99.8) 16O, but...Ch. 19.6 - Prob. 9P Ch. 19.8 - Show the products you would obtain by...

Chapter 19 Solutions