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 1

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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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Why doesn't this carry on to form a ring by deprotonating the alpha carbon and the negatively-charged carbon attacking the C=O?

6. A solution (0.0004 M) of Fe(S2CNEt2)3 (see the structural drawing below) in chloroform has absorption bands at: 350 nm (absorbance A = 2.34); 514 nm(absorbance A = 0.0532); Calculate the molar absorptivity values for these bands. Comment on their possible nature (charge transfer transitions or d-d S N- transitions?). (4 points)

What is the mechanism for this?

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

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 18.9P

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.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

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 18.9P

Interpretation Introduction