Quiz - Alcohols, Ethers, Epoxides | Reactivity of Alcohols, Ethers and Epoxides
Which of the following types of reactions corresponds to the transformation of an alcohol into a ketone?
Substitution
Elimination
Oxidation
Deprotonation
Which of the following reagents causes alcohol substitution?
PBr3
SOCl2
CH3SO2Cl
All of the above
One of the typical reactions of alcohols is the substitution of HO- by another chemical group using for example PBr3 or SOCl2. However, HO- is a bad leaving group and can be replaced with a better leaving group like mesyl chloride CH3SO2Cl to favor SN reactions
Which of the following reagents is best for deprotonating alcohol?
KH
NaOH
Et3N
NH3
pKa of alcohols ~ 16-18 ⇒ strong bases are needed to deprotonate alcohols. Common strong bases: LDA, butyl lithium (BuLi), potassium hydride (KH)
Which of the following compounds reacts with chloroethane to form diethyl ether?
EtONa
Na2Cr2O7
H2SO4
CH3CH2OH
Linear ethers can be synthesized by intramolecular SN reactions: EtCl + EtONa → EtOEt + NaCl
Which of the following reactions is the Williamson ether synthesis
alkoxide with a metal
alkoxide with an haloalkane
alcohol with an haloalkane
aldehyde with a metal
The Williamson ether synthesis is an organic reaction, forming an ether from an haloalkane and a deprotonated alcohol (alkoxide)
Under what condition does the nucleophile attack the more hindered site of an epoxide?
When the nucleophile is small and highly reactive
When the reaction is base-catalyzed
When the reaction is acid-catalyzed
There is no stereoselectivity with epoxides
Mechanism of acid catalyzed ring opening:
