1-Octene-3-ol can be prepared from hexanal in two steps. The first step involves an actylide addition reaction to hexanal. The structure of the product formed in this step is to be given and how to convert it in to 1-octene-3-ol is also to be stated. Concept introduction: When aldehydes and ketones are treated with sodium acetylide in the presence of dilute acids addition reaction occurs. The acetylide ion adds to the carbonyl carbon of the aldehyde and H adds to the carbonyl oxygen to yield an ynol in which the alcohol group is adjacent to a carbon in triple bond. To give: The structure of the product formed in the step during the reaction between hexanal and sodium acetylide in the presence of dilute acids and further to state how it can be converted in to 1-octene-3-ol.

Question

Which stereoisomer of 3-hexene forms (3S,4S)-4-bromo-3-hexanol and (3R,4R)-4-bromo-3-hexanol when it reacts with Br2 and H2O?

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 9.SE, Problem 52AP

Interpretation Introduction

Interpretation:

1-Octene-3-ol can be prepared from hexanal in two steps. The first step involves an actylide addition reaction to hexanal. The structure of the product formed in this step is to be given and how to convert it in to 1-octene-3-ol is also to be stated.

Concept introduction:

When aldehydes and ketones are treated with sodium acetylide in the presence of dilute acids addition reaction occurs. The acetylide ion adds to the carbonyl carbon of the aldehyde and H adds to the carbonyl oxygen to yield an ynol in which the alcohol group is adjacent to a carbon in triple bond.

To give:

The structure of the product formed in the step during the reaction between hexanal and sodium acetylide in the presence of dilute acids and further to state how it can be converted in to 1-octene-3-ol.

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Which stereoisomer of 3-hexene forms (3S,4S)-4-bromo-3-hexanol and (3R,4R)-4-bromo-3-hexanol when it reacts with Br2 and H2O?

1. What type of reaction is occuring in step 3? (halogenation, hydrohalogenation, reduction, keto–enol tautomerism, dehydrohalogenation, acid-catalyzed hydration, base-catalyzed hydration) 2. Which reagent is necessary for step 3? (Br2, HBr, H2/Pt, NaNH2, H20/H2SO4/HgSO4)

What alkene is needed to synthesize each 1,2-diol using [1] OsO4 followed by NaHSO3 in H2O; or [2] CH3CO3H followed by −OH in H2O?

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 9.SE, Problem 52AP

Interpretation Introduction

Interpretation:

1-Octene-3-ol can be prepared from hexanal in two steps. The first step involves an actylide addition reaction to hexanal. The structure of the product formed in this step is to be given and how to convert it in to 1-octene-3-ol is also to be stated.

Concept introduction:

When aldehydes and ketones are treated with sodium acetylide in the presence of dilute acids addition reaction occurs. The acetylide ion adds to the carbonyl carbon of the aldehyde and H adds to the carbonyl oxygen to yield an ynol in which the alcohol group is adjacent to a carbon in triple bond.

To give:

The structure of the product formed in the step during the reaction between hexanal and sodium acetylide in the presence of dilute acids and further to state how it can be converted in to 1-octene-3-ol.

Expert Solution & Answer

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Check out sample textbook solution

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 9.SE, Problem 52AP

Interpretation Introduction

Interpretation:

1-Octene-3-ol can be prepared from hexanal in two steps. The first step involves an actylide addition reaction to hexanal. The structure of the product formed in this step is to be given and how to convert it in to 1-octene-3-ol is also to be stated.

Concept introduction:

When aldehydes and ketones are treated with sodium acetylide in the presence of dilute acids addition reaction occurs. The acetylide ion adds to the carbonyl carbon of the aldehyde and H adds to the carbonyl oxygen to yield an ynol in which the alcohol group is adjacent to a carbon in triple bond.

To give:

The structure of the product formed in the step during the reaction between hexanal and sodium acetylide in the presence of dilute acids and further to state how it can be converted in to 1-octene-3-ol.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook 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 9.SE, Problem 52AP

Interpretation Introduction