Quiz - Alcohols, Ethers, Epoxides | Reactivity of Alcohols, Ethers and Epoxides

1

Which of the following types of reactions corresponds to the transformation of an alcohol into a ketone?

Substitution

Elimination

Oxidation

Deprotonation

2

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

3

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)

4

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

5

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)

6

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: