Organic Chemistry III

Professor Carl C. Wamser

Chem 336 - Spring 2009

Pre-Quiz 21

(must be done in Blackboard before Fri., April 10, 8:30 am)

1. Claisen condensation of ethyl butanoate would give

a. ethyl octanoate
b. ethyl hexanoate
c. ethyl 2-methylhexanoate
d. ethyl 2-ethyl-3-oxopentanoate
* e. ethyl 2-ethyl-3-oxohexanoate

2. Claisen condensation is never done with aqueous base because the reaction instead would be

a. transesterification
b. enolization
* c. saponification
d. Michael addition
e. SN2 substitution

3. Malonic ester synthesis of hexanoic acid would require

a. bromoethane
* b. 1-bromobutane
c. 1-bromopentane
d. 1-bromohexane
e. 1,1-dibromohexane

4. Dieckmann condensation followed by hydrolysis and decarboxylation would be a method to form

a. a carboxylic acid
* b. a ketone
c. a cyclic ester
d. an anhydride
e. a diester

5. In general, the alpha-hydrogens on an ester, compared to a ketone, are

a. stronger acids
* b. weaker acids