
(a)
Interpretation:
The structure of the compound
Concept introduction:
Sharpless asymmetric epoxidation: An
Sharpless catalyst consists of Titanium tetraisopropoxide and one enantiomer of Diethyl tartrate (
A chiral complex is formed with Titanium tetraisopropoxide and with either
(b)
Interpretation:
The plausible mechanism for the transformation of
Concept introduction:
Ring-opening of epoxide:
The epoxide ring is highly strain and readily undergoes reaction with strong nucleophile result in the ring-opening reaction.
Base catalyzed ring opening of epoxide:
The nucleophile will attack at the less substituted position under basic conditions
(c)
Interpretation:
The structure of
Concept introduction:
Protection of alcohols as TMS Ethers:
The use of TMSCl and a base is used to form TMS ethers. Primary, secondary and tertiary alcohols can be silylated using TMSCl
Methanesulfonates also can be used as a protecting group for alcohols.
(d)
Interpretation:
The plausible mechanism for the transformation of
Concept introduction:
Deprotonation: The reaction in which proton is removed from the compound using reagents is known as deprotonation.
Nucleophile: donates pair of electrons to positively charged substrate resulting in the formation of

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Chapter 13 Solutions
Organic Chemistry, Third Edition Binder Ready Version
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