Chapter 24, Problem 24.40P

(a)

Interpretation Introduction

Interpretation:

The types of functional groups present in estrone have to be named.

Concept introduction:

Functional groups:

The functional group is defined as an atom or group of atoms combined in a specific manner that gives the chemical properties of the organic compound and they are the main reason for the chemical reactivity of the compound.  Compounds having similar functional groups undergoes similar type of reactions.

(b)

Interpretation Introduction

Interpretation:

The number of chiral centres present in estrone that has to be calculated.

Concept introduction:

Chiral centre:

Chiral centre is defined as an atom bonded to four different chemical species.  It is a stereo centre that holds the atom in such way that the structure may not be superimposable to its mirror image.  They give optical isomerism.

(c)

Interpretation Introduction

Interpretation:

Structural formula for the compounds $\text{(2)}$ and $\text{(3)}$ asked in the question have to be given.

Concept introduction:

Structural formula:

The structural formula of a compound can be defined as a graphic representation of the molecular structure showing how the atoms are arranged and the chemical bonding between the molecules is also shown explicitly or implicitly.

Retrosynthetic approach:

Retrosynthetic analysis is a technique for planning a synthesis mainly for complex organic molecules where the complex target molecule is reduced into a sequence of progressively simpler structures along a pathway which ultimately leads to the identification of a simple starting molecule or easily available from which the synthesis can be developed.

During retrosynthetic analysis the target molecule is symmetrically broken down by a combination of functional group interconversion and disconnection.  This disconnection is related to breaking of carbon-carbon bond of a molecule to generate simpler fragments.  The complete set of disconnections and functional group interconversions for a specified target molecule is what constitutes a retrosynthetic plan.

Heck reaction:

The Heck reaction is the chemical reaction of an unsaturated halide with an alkene in presence of a base and palladium catalyst to form a substituted alkene.  The reaction is as follows,

(d)

Interpretation Introduction

Interpretation:

The pathway of converting compounds $\text{(2)}$ and $\text{(3)}$ to compound $\text{(1)}$ has to be proposed.

Concept introduction:

Heck reaction:

The Heck reaction is the chemical reaction of an unsaturated halide with an alkene in presence of a base and palladium catalyst to form a substituted alkene.  The reaction is as follows,

(e)

Interpretation Introduction

Interpretation:

The stereochemistry of compound $\text{(1)}$ has to be determined assuming in compound $\text{(3)}$ the precursor to the rings C and D of estrone, that the fusion of the rings C and D is trans and that the angular methyl group is above the plane of the ring.

Concept introduction:

The Heck reaction is the chemical reaction of an unsaturated halide with an alkene in presence of a base and palladium catalyst to form a substituted alkene.  The reaction is as follows,

(f)

Interpretation Introduction

Interpretation:

The pathway of conversion of tertiary butyl ether to acetone to form estrone from compound $\text{(1)}$ has to be determined.

Concept introduction:

Oxidation of secondary alcohol:

Oxidation of alcohol to carbonyl is very difficult as the reaction is so fast that it always ends up by giving acid.  Hence for secondary alcohol to get oxidised to carbonyl selectively PCC is used.