Review the key concepts, formulae, and examples before starting your quiz.
πConcepts
IUPAC Nomenclature: Alcohols are named by replacing the '-e' of the parent alkane with '-ol'. For phenols, the parent structure is . Ethers are named as 'alkoxyalkanes' where the smaller alkyl group is the 'alkoxy' part.
Preparation of Alcohols via Hydration: Acid-catalyzed hydration of alkenes follows Markovnikov's rule, e.g., .
Hydroboration-Oxidation: A method to prepare alcohols from alkenes yielding anti-Markovnikov products. The reagent used is diborane () followed by alkaline .
Grignard Synthesis: Reaction of with formaldehyde gives a primary () alcohol, with other aldehydes gives a secondary () alcohol, and with ketones gives a tertiary () alcohol.
Preparation of Phenol from Cumene: Isopropylbenzene () is oxidized by air to cumene hydroperoxide, which is then hydrolyzed by dilute acid to yield phenol () and acetone ().
Williamson Ether Synthesis: An reaction between a primary alkyl halide and a sodium alkoxide (). It is the preferred method for preparing unsymmetrical ethers.
Dehydration of Alcohols: At in the presence of , primary alcohols undergo intermolecular dehydration to form ethers: .
πFormulae
π‘Examples
Problem 1:
Predict the product when Propanone reacts with Methylmagnesium bromide followed by hydrolysis.
Solution:
The product is 2-Methylpropan-2-ol ().
Explanation:
Propanone () is a ketone. Grignard reagents () react with ketones to form an adduct which, upon hydrolysis, yields a tertiary alcohol: .
Problem 2:
Why is it not possible to prepare tert-butyl ethyl ether by reacting sodium ethoxide with tert-butyl bromide?
Solution:
Reaction will lead to the formation of Isobutylene () instead of the ether.
Explanation:
Tert-butyl bromide is a tertiary () alkyl halide. In the presence of a strong base like sodium ethoxide (), halides undergo elimination (E2) rather than substitution () to form an alkene. To prepare this ether, one should react sodium tert-butoxide with ethyl bromide.
Problem 3:
Identify the major product of the acid-catalyzed hydration of But-1-ene.
Solution:
The major product is Butan-2-ol ().
Explanation:
According to Markovnikov's rule, the hydrogen atom of the water molecule () adds to the carbon of the double bond with more hydrogen atoms, and the hydroxyl group adds to the more substituted carbon.