The structures of oximene and myrcene are to be identified. Concept introduction: In the presence of ozone and CH 3 SCH 3 , oxidative cleavage occurs. In oxidative cleavage both the sigma and pi bond of the alkene is broken and two carbonyl compounds are formed. Depending upon the alkyl substituents, aldehyde or ketone is formed. When ozone is added to the alkene, unstable intermediate molozonide is formed which rearranges to ozonide. This ozonide is reduced to form two carbonyl compounds in presence of CH 3 SCH 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 12, Problem 50P

Interpretation Introduction

Interpretation: The structures of oximene and myrcene are to be identified.

Concept introduction: In the presence of ozone and CH3SCH3, oxidative cleavage occurs. In oxidative cleavage both the sigma and pi bond of the alkene is broken and two carbonyl compounds are formed. Depending upon the alkyl substituents, aldehyde or ketone is formed. When ozone is added to the alkene, unstable intermediate molozonide is formed which rearranges to ozonide. This ozonide is reduced to form two carbonyl compounds in presence of CH3SCH3.

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Using what we have learned in CHEM 2310 and up through class on 1/31, propose a series of reaction steps to achieve the transformation below. Be sure to show all reagents and intermediates for full credit. You do not need to draw mechanism arrows, but you do need to include charges where appropriate. If you do not put your group name, you will get half credit at most. ? Br

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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 12, Problem 50P

Interpretation Introduction

Interpretation: The structures of oximene and myrcene are to be identified.

Concept introduction: In the presence of ozone and CH3SCH3, oxidative cleavage occurs. In oxidative cleavage both the sigma and pi bond of the alkene is broken and two carbonyl compounds are formed. Depending upon the alkyl substituents, aldehyde or ketone is formed. When ozone is added to the alkene, unstable intermediate molozonide is formed which rearranges to ozonide. This ozonide is reduced to form two carbonyl compounds in presence of CH3SCH3.

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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 12, Problem 50P

Interpretation Introduction

Interpretation: The structures of oximene and myrcene are to be identified.

Concept introduction: In the presence of ozone and CH3SCH3, oxidative cleavage occurs. In oxidative cleavage both the sigma and pi bond of the alkene is broken and two carbonyl compounds are formed. Depending upon the alkyl substituents, aldehyde or ketone is formed. When ozone is added to the alkene, unstable intermediate molozonide is formed which rearranges to ozonide. This ozonide is reduced to form two carbonyl compounds in presence of CH3SCH3.

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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 12, Problem 50P

Interpretation Introduction