Synthesis of the molecule is to be shown using an Aldol condensation. Concept introduction: If we see the molecule, we find that it is an α,β- unsaturated carbonyl compound. The molecule is an α,β- unsaturated aldehyde , so it can be the product of dehydrating the β- hydroxy aldehyde. To apply a transform that undoes an aldol addition, we must disconnect the bond between α and β carbons. Because the resulting aldehyde precursors are different from each other, more than one aldol product is possible in the forward direction. To produce the desired product only, we should slowly add the aldehyde with α- hydrogens to a basic solution of the aldehyde without α- hydrogens.

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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 18, Problem 18.29P

Interpretation Introduction

Interpretation:

Synthesis of the molecule is to be shown using an Aldol condensation.

Concept introduction:

If we see the molecule, we find that it is an α,β- unsaturated carbonyl compound. The molecule is an α,β- unsaturated aldehyde, so it can be the product of dehydrating the β- hydroxy aldehyde. To apply a transform that undoes an aldol addition, we must disconnect the bond between α and β carbons. Because the resulting aldehyde precursors are different from each other, more than one aldol product is possible in the forward direction. To produce the desired product only, we should slowly add the aldehyde with α- hydrogens to a basic solution of the aldehyde without α- hydrogens.

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Done 11:14 ⚫ worksheets.beyondlabz.com 5 (a). Using the peak information you listed in the tables for both structures, assign each peak to that portion of the structure that produces the peak in the NMR spectrum. Draw this diagram on your own sheet of paper and attach the sketch of your drawing to this question. Question 6 5 (b). Using the peak information you listed in the tables for both structures, assign each peak to that portion of the structure that produces the peak in the NMR spectrum. Draw this diagram on your own sheet of paper and attach the sketch of your drawing to this question. Question 7 6. Are there any differences between the spectra you obtained in Beyond Labz and the predicted spectra? If so, what were the differences? <

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**

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 18, Problem 18.29P

Interpretation Introduction

Interpretation:

Synthesis of the molecule is to be shown using an Aldol condensation.

Concept introduction:

If we see the molecule, we find that it is an α,β- unsaturated carbonyl compound. The molecule is an α,β- unsaturated aldehyde, so it can be the product of dehydrating the β- hydroxy aldehyde. To apply a transform that undoes an aldol addition, we must disconnect the bond between α and β carbons. Because the resulting aldehyde precursors are different from each other, more than one aldol product is possible in the forward direction. To produce the desired product only, we should slowly add the aldehyde with α- hydrogens to a basic solution of the aldehyde without α- hydrogens.

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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 18, Problem 18.29P

Interpretation Introduction

Interpretation:

Synthesis of the molecule is to be shown using an Aldol condensation.

Concept introduction:

If we see the molecule, we find that it is an α,β- unsaturated carbonyl compound. The molecule is an α,β- unsaturated aldehyde, so it can be the product of dehydrating the β- hydroxy aldehyde. To apply a transform that undoes an aldol addition, we must disconnect the bond between α and β carbons. Because the resulting aldehyde precursors are different from each other, more than one aldol product is possible in the forward direction. To produce the desired product only, we should slowly add the aldehyde with α- hydrogens to a basic solution of the aldehyde without α- hydrogens.

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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 18, Problem 18.29P

Interpretation Introduction