The observation, when the unsymmetrical ketone , 2-methylcyclohexenone is converted into an enamine the sole product is the one with the double bond opposite to the methyl substituted carbon while the other possible enamine with methyl on the carbon in double bond is not formed, is to be explained. Concept introduction: The enamine obtained from an unsymmetrical ketone will be stable only if it is free from steric strain. A strained unsymmetrical ketone will be unstable. To explain: The observation, when the unsymmetrical ketone, 2-methylcyclohexenone is converted into an enamine the sole product is the one with the double bond opposite to the methyl substituted carbon while the other possible enamine with methyl on the carbon in double bond is not formed.

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 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 23.SE, Problem 73AP

Interpretation Introduction

Interpretation:

The observation, when the unsymmetrical ketone, 2-methylcyclohexenone is converted into an enamine the sole product is the one with the double bond opposite to the methyl substituted carbon while the other possible enamine with methyl on the carbon in double bond is not formed, is to be explained.

Concept introduction:

The enamine obtained from an unsymmetrical ketone will be stable only if it is free from steric strain. A strained unsymmetrical ketone will be unstable.

To explain:

The observation, when the unsymmetrical ketone, 2-methylcyclohexenone is converted into an enamine the sole product is the one with the double bond opposite to the methyl substituted carbon while the other possible enamine with methyl on the carbon in double bond is not formed.

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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 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 23.SE, Problem 73AP

Interpretation Introduction

Interpretation:

The observation, when the unsymmetrical ketone, 2-methylcyclohexenone is converted into an enamine the sole product is the one with the double bond opposite to the methyl substituted carbon while the other possible enamine with methyl on the carbon in double bond is not formed, is to be explained.

Concept introduction:

The enamine obtained from an unsymmetrical ketone will be stable only if it is free from steric strain. A strained unsymmetrical ketone will be unstable.

To explain:

The observation, when the unsymmetrical ketone, 2-methylcyclohexenone is converted into an enamine the sole product is the one with the double bond opposite to the methyl substituted carbon while the other possible enamine with methyl on the carbon in double bond is not formed.

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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 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 23.SE, Problem 73AP

Interpretation Introduction

Interpretation:

The observation, when the unsymmetrical ketone, 2-methylcyclohexenone is converted into an enamine the sole product is the one with the double bond opposite to the methyl substituted carbon while the other possible enamine with methyl on the carbon in double bond is not formed, is to be explained.

Concept introduction:

The enamine obtained from an unsymmetrical ketone will be stable only if it is free from steric strain. A strained unsymmetrical ketone will be unstable.

To explain:

The observation, when the unsymmetrical ketone, 2-methylcyclohexenone is converted into an enamine the sole product is the one with the double bond opposite to the methyl substituted carbon while the other possible enamine with methyl on the carbon in double bond is not formed.

Expert Solution & Answer

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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 23.SE, Problem 73AP

Interpretation Introduction