FGI's & Drug synthesis Flashcards
How can alcohols be prepared?
Alkene hydration
Reduction of carbonyls
- aldehydes
- ketones
How can ethers be prepared?
Dehydration of alcohols
Williamson synthesis
What type of ether is formed by the dehydration of alcohols?
Symmetrical
- the R groups are the same
What type of ether is formed by the Williamson synthesis?
Asymmetrical
Why is dehydration of alcohols to make ethers limited to primary alcohols?
Secondary and tertiary alcohols are sterically hindered
What are the steps involved in Williamson synthesis of ethers?
Generation of alkoxide
SN2 reaction with alkyl halide
The first step is proton transfer
the second step is nucleophilic attack
How do you know when step 1 of a Williamson synthesis of ethers reaction has finished?
Hydrogen is produced during the reaction
- the bubbles stop when it has finished
What is the Williamson synthesis of ethers?
SN2 reaction with an alkoxide as the nucleophile
What are the steps involved in the synthesis of Propranolol?
Generation of alkoxide
Williamson ether synthesis
Nucleophilic epoxied ring opening
What is an organometallic compound?
R-M
M = Li, Mg, Cd, Zn
Give examples of common organometallic reagents
Grignard reagents
- R-Mg-I
Alkyl/aryl lithium reagents
- R-Li
R is an anion (R-) as M are positive charges
What is Terfenadine a prodrug for?
Fexofenadine
What is fexofenadine used for?
Antihistamine
