A complete and detailed mechanism for 1 , 3 − dithiane formation reaction is to be drawn. Concept introduction: If an aldehyde or ketone is treated with a large excess of an alcohol under acidic conditions, then the hemiacetal produced from nucleophilic addition reacts further to form an acetal, in which two alkoxy ( RO ) groups are bonded to the same carbon. The complete mechanism for this acetal formation reaction is shown in Equation 18-13: The sulfur analog of an acetal is produced when a ketone or aldehyde is treated with a thiol ( RSH ) under acidic conditions. This is called as thioacetal. When propane − 1 , 3 − dithiol is used, 1 , 3 − dithiane is produced. The mechanism is the same as that of equation 18-13. The only difference is that the coordination step 6 is intramolecular rather than intermolecular.

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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 18.9P

Interpretation Introduction

Interpretation:

A complete and detailed mechanism for 1,3−dithiane formation reaction is to be drawn.

Concept introduction:

If an aldehyde or ketone is treated with a large excess of an alcohol under acidic conditions, then the hemiacetal produced from nucleophilic addition reacts further to form an acetal, in which two alkoxy (RO) groups are bonded to the same carbon. The complete mechanism for this acetal formation reaction is shown in Equation 18-13:

The sulfur analog of an acetal is produced when a ketone or aldehyde is treated with a thiol (RSH) under acidic conditions. This is called as thioacetal. When propane−1,3−dithiol is used, 1,3−dithiane is produced. The mechanism is the same as that of equation 18-13. The only difference is that the coordination step 6 is intramolecular rather than intermolecular.

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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

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 18.9P

Interpretation Introduction

Interpretation:

A complete and detailed mechanism for 1,3−dithiane formation reaction is to be drawn.

Concept introduction:

If an aldehyde or ketone is treated with a large excess of an alcohol under acidic conditions, then the hemiacetal produced from nucleophilic addition reacts further to form an acetal, in which two alkoxy (RO) groups are bonded to the same carbon. The complete mechanism for this acetal formation reaction is shown in Equation 18-13:

The sulfur analog of an acetal is produced when a ketone or aldehyde is treated with a thiol (RSH) under acidic conditions. This is called as thioacetal. When propane−1,3−dithiol is used, 1,3−dithiane is produced. The mechanism is the same as that of equation 18-13. The only difference is that the coordination step 6 is intramolecular rather than intermolecular.

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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 18, Problem 18.9P

Interpretation Introduction

Interpretation:

A complete and detailed mechanism for 1,3−dithiane formation reaction is to be drawn.

Concept introduction:

If an aldehyde or ketone is treated with a large excess of an alcohol under acidic conditions, then the hemiacetal produced from nucleophilic addition reacts further to form an acetal, in which two alkoxy (RO) groups are bonded to the same carbon. The complete mechanism for this acetal formation reaction is shown in Equation 18-13:

The sulfur analog of an acetal is produced when a ketone or aldehyde is treated with a thiol (RSH) under acidic conditions. This is called as thioacetal. When propane−1,3−dithiol is used, 1,3−dithiane is produced. The mechanism is the same as that of equation 18-13. The only difference is that the coordination step 6 is intramolecular rather than intermolecular.

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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 18, Problem 18.9P

Interpretation Introduction