Chapter 26, Problem 52IP

(a)

Interpretation Introduction

Interpretation:

The products expected need to be identified when estradiol is treated with the given set of reagents.

Concept introduction:

Bromination is a reaction in which bromine atom is substituted in the compound.  Various reagents can be used for bromination.  Few of them are, bromine, N-bromosuccinimide etc.  In case of aromatic substitution the groups already present in the aromatic ring direct the position of bromine substitution.  If the group already present in the aromatic ring is a ortho-, para- directing group the substitution takes place in ortho and para position.  If the group already present in the aromatic ring is meta- directing means the substitution takes place in meta- position.

To draw: the product obtained when estradiol is treated with excess bromine.

(b)

Interpretation Introduction

Interpretation:

The products expected need to be identified when estradiol is treated with the given set of reagents.

Concept introduction:

Oxidation can be done using $\text{PCC}$.  As $\text{PCC}$ is a mild oxidizing agent it oxidizes primary alcohol to aldehyde and secondary alcohol to ketone.  It is not a strong oxidizing agent to oxidize aldehyde to carboxylic acid.

To draw: the structure of product obtained when estradiol is treated with $\text{PCC}$.

(c)

Interpretation Introduction

Interpretation:

The products expected need to be identified when estradiol is treated with the given set of reagents.

Concept introduction:

When alcohol is treated with a strong base deprotonation happens and in presence of alkyl halide, alkylation reaction takes place.

To draw: the structure of product obtained when estradiol is treated with a strong base and ethyl iodide

(d)

Interpretation Introduction

Interpretation:

The products expected need to be identified when estradiol is treated with the given set of reagents.

Concept introduction:

When alcohol is treated with acetyl chloride in presence of pyridine, acetylation happens.  The hydroxyl group is converted to $\text{OAc}$ group. Pyridine acts as a nucleophilic catalyst and it takes part in the reaction.

To draw: the structure of product obtained when estradiol is treated with acetyl chloride in presence of pyridine