Organic Chemistry 2 Problem Set: Aldehydes & Ketones

1. Draw the structure of a ketone with four alpha hydrogens.

(a) What is its IUPAC name?
(b) Can it form H-bonding with a molecule of the same type?
(c) Do you think the compound will be soluble,slightly soluble or
insoluble in water? Explain.
(d) Will it react with tollen’s reagent? If yes, give the structure of the
product.

2. Predict the products in each of the following reactions:

(a) phenyl acetaldehyde, C6H5CH2CHO + NaBH4 then H3O+
(b) acetaldehyde treated with Phenylmagnesiumbromide then H3O+
(c) 2,2-dimethyl-3-pentanone + NH2OH/H+
(d) 3-Methylcyclopentanone + H2O/acid catalyst

3. Use a Grignard reaction on an aldehyde or ketone to synthesize 1-

Phenylcyclopentanol.

4. Show structures of the intermediate hemiacetal and the final acetal

that result from the reaction of Acetone and + cyclopentanol and acid
catalyst.

5. Starting with Benzyl alcohol (C6H5CH2OH) and any other

reagents needed, synthesize benzophenone.

6. Write the COMPLETE mechanism for each of the following

reactions:
(a) Cyclohexanone + HCN/ -CN
(b) Cyclopentanone + 1,2-Ethanediol/H+
(c) Benzaldehyde + H2NCH2CH3/mild H+