
(a)
Interpretation:
The types of
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:
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:
Structural formula for the compounds
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
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
(d)
Interpretation:
The pathway of converting compounds
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:
The stereochemistry of compound
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:
The pathway of conversion of tertiary butyl ether to acetone to form estrone from compound
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.

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Chapter 24 Solutions
Organic Chemistry
- (c) (4pts) Mechanism: heat (E1) CH3OH + 1.5pts each _E1 _ (1pt) Br CH3OH (d) (4pts) Mechanism: SN1 (1pt) (e) (3pts) 1111 I H 10 Ill!! H LDA THF (solvent) Mechanism: E2 (1pt) NC (f) Bri!!!!! CH3 NaCN (3pts) acetone Mechanism: SN2 (1pt) (SN1) -OCH3 OCH3 1.5pts each 2pts for either product 1pt if incorrect stereochemistry H Br (g) “,、 (3pts) H CH3OH +21 Mechanism: SN2 (1pt) H CH3 2pts 1pt if incorrect stereochemistry H 2pts 1pt if incorrect stereochemistryarrow_forwardA mixture of butyl acrylate and 4'-chloropropiophenone has been taken for proton NMR analysis. Based on this proton NMR, determine the relative percentage of each compound in the mixturearrow_forwardQ5: Label each chiral carbon in the following molecules as R or S. Make sure the stereocenter to which each of your R/S assignments belong is perfectly clear to the grader. (8pts) R OCH 3 CI H S 2pts for each R/S HO R H !!! I OH CI HN CI R Harrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning

