CHE 302
Summer 2006
Chapter 18: Aldehydes and Ketones II Worksheet Answers
REACTIONS:
1. formaldehyde + (conc.) NaOH  HCOO- + methanol
Crossed Canizzaro
OH
2. acetone + NaCN, H  CH3CCH3
C≡N
Addition with Cyanide
+
H
3. methanal + (xs) ethanol, dry HCl  CH3CH2OCOCH2CH3
H
Addition of Alcohols  Acetal formation
4. acetaldehyde + NH2NHCONH2 (semicarbazide)  CH3CH=NNHCONH2
Addition with derivatives of Ammonia
5. ethanal + alcoholic silver nitrate (Tollen’s reagent)  CH3COO- + Ag
Tollen’s Test for aldehydes
OH
6. acetophenone +H2, Ni  Ph-CHCH3
Hydride Reduction
SYNTHESIS OF ALCOHOLS USING GRIGNARD REAGENTS AND CARBONYL COMPOUNDS:
Draw the structures of the Grignard reagent and the carbonyl compound that can be
combined to give the following alcohols.
1. 2-hexanol  CH3CH2CH2CH2MgBr + ethanal or ?
2. 3-phenyl-1-propanol  PhCH2CH2MgBr + formaldehyde (a.k.a. methanal)
3. 2-methyl-2-butanol  CH3CH2MgBr + propanone
CHE 302
Summer 2006
Outline a possible laboratory synthesis of each of the following compounds starting with
alcohols of four-carbons or less, benzene, cyclohexanol and any needed inorganic
reagents.
1. cyclohexylmethanol
a. cyclohexanol + HBr; Mg;
b. methanol + PCC
2. 3-methyl-1-butene
N/A. See me at office hours.
H2O