Chem223 practice exam (pre final)

Short answer questions

Question 1: Give the product(s) or reagents (as required) of the following reactions. Note: transformation
conditions may include more than one reaction.

1) BH3.THF

2) H2O2, NaOH

HBr

peroxide and light

(one step)

Br2, EtOH

CH3

1) Me2CuLi
O
2) H2O

CH2

1) PPh3
2) NaH

Br 3) acetone

HCl

O O
1) NaOEt / EtOH

2) H3O+

1
 O O
CN
1) EtMgBr
OH OMe

2) H2O

O O O

O
O O

Ph Me
Me COOPh Ph OH

Question 2:
a) Fill in the boxes
Cat. H2SO4
(conditions or products,
O N C1
as required). H
CN
b) Suggest a milder
method to generate the A B 1) LDA, -78 C

bottom left product C2

2) Ph-CH2Br
from reagent B. C2

Part 3: Long answer questions

Question 1: Propose a synthetic sequence to prepare the following molecule from the starting
material indicated below for each case. Any reagent using inorganic or main group elements (C
excluded) may be used. Note: In this context, PPh3 will be considered a main group element reagent and its
carbon content does not need to be counted.
O OH
a) b) c)

OH

From two molecules of PhCHO and From something with 7 carbon From something with 6 carbon
other reagents with less than two atoms or less (no need to worry atoms or less.
carbon atoms. about alkene stereochemistry)
Note: On the final exam, youll also be asked mechanisms for given reaction (on all the lecture material).