Quiz - Reactivity of Alcohols, Ethers, and Epoxides - 1 | Reactivity of Alcohols, Ethers, and Epoxides

Organic Chemistry 1 - Quiz - Reactivity of Alcohols, Ethers, and Epoxides - 1


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


Which of the following reagents causes alcohol substitution?

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?

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?

Linear ethers can be synthesized by intramolecular SN reactions: EtCl + EtONa → EtOEt + NaCl


Which of the following reactions is the Williamson ether synthesis?

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?

Mechanism of acid catalyzed ring opening:


What type of reaction mechanism is typically involved in the dehydration of alcohols?

The dehydration of alcohols typically proceeds via an elimination reaction mechanism, where a water molecule is removed from the alcohol to form an alkene.


Which of the following alcohols would be most readily dehydrated?

Tertiary alcohols are more readily dehydrated compared to primary and secondary alcohols due to the stability of the carbocation intermediate formed during the dehydration process. This stabilization lowers the energy barrier for the formation of the carbocation intermediate, making the dehydration reaction more favorable.


Why are epoxides generally more reactive compared to simple ethers in nucleophilic substitution reactions?

Epoxides are more reactive than simple ethers due to the strain present in their three-membered rings, making them susceptible to ring-opening reactions.


In the formation of alkyl halides from tertiary alcohols with hydrogen halides, which mechanism is commonly observed?


The formation of alkyl halides from tertiary alcohols with hydrogen halides typically proceeds via an SN1 (nucleophilic substitution unimolecular) mechanism, involving the formation of a carbocation intermediate.