The complete and detailed mechanism of the Robinson annulation reaction given in Equation 18-55 is to be drawn. Concept introduction: A Robinson annulation reaction is a Michael reaction, the conjugate addition of an enolate anion, followed by intramolecular aldol condensation. One of the reactants of a Robinson annulation must be an α, β- unsaturated carbonyl compound with two acidic α -protons. The second must be a ketone or aldehyde with one acidic α -proton

Question

Draw structures corresponding to the following names and give IUPAC names for the following compounds: (8 Point) a) b) c) CH3 CH2CH3 CH3CHCH2CH2CH CH3 C=C H3C H H2C=C=CHCH3 d) CI e) (3E,5Z)-2,6-Dimethyl-1,3,5,7-octatetraene f) (Z)-4-bromo-3-methyl-3-penten-1-yne g) cis-1-Bromo-2-ethylcyclopentane h) (5R)-4,4,5-trichloro-3,3-dimethyldecane

Answer 1

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 18.37P

Interpretation Introduction

Interpretation:

The complete and detailed mechanism of the Robinson annulation reaction given in Equation 18-55 is to be drawn.

Concept introduction:

A Robinson annulation reaction is a Michael reaction, the conjugate addition of an enolate anion, followed by intramolecular aldol condensation. One of the reactants of a Robinson annulation must be an α, β- unsaturated carbonyl compound with two acidic α-protons. The second must be a ketone or aldehyde with one acidic α-proton

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Draw structures corresponding to the following names and give IUPAC names for the following compounds: (8 Point) a) b) c) CH3 CH2CH3 CH3CHCH2CH2CH CH3 C=C H3C H H2C=C=CHCH3 d) CI e) (3E,5Z)-2,6-Dimethyl-1,3,5,7-octatetraene f) (Z)-4-bromo-3-methyl-3-penten-1-yne g) cis-1-Bromo-2-ethylcyclopentane h) (5R)-4,4,5-trichloro-3,3-dimethyldecane

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Review: Design a total total synthesis synthesis of the following compound using methyloxacyclopropane and any other necessary reagents.

Answer 2

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 18.37P

Interpretation Introduction

Interpretation:

The complete and detailed mechanism of the Robinson annulation reaction given in Equation 18-55 is to be drawn.

Concept introduction:

A Robinson annulation reaction is a Michael reaction, the conjugate addition of an enolate anion, followed by intramolecular aldol condensation. One of the reactants of a Robinson annulation must be an α, β- unsaturated carbonyl compound with two acidic α-protons. The second must be a ketone or aldehyde with one acidic α-proton

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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 18.37P

Interpretation Introduction

Interpretation:

The complete and detailed mechanism of the Robinson annulation reaction given in Equation 18-55 is to be drawn.

Concept introduction:

A Robinson annulation reaction is a Michael reaction, the conjugate addition of an enolate anion, followed by intramolecular aldol condensation. One of the reactants of a Robinson annulation must be an α, β- unsaturated carbonyl compound with two acidic α-protons. The second must be a ketone or aldehyde with one acidic α-proton

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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 18.37P

Interpretation Introduction