2007 test_1a_answers - Chemistry 2203/7'07 TEST 1A Name...

Chemistry 2203/7 (’07) TEST 1A Name: ____________________________ Page1/1
TEST WILL BE DISCUSSED IN TUTORIAL THIS FRIDAY 1130 AT 301
Marks are in parentheses
1 . (6) For the molecules below, provide a systematic name ( 2 x 2 marks ) and indicate with an arrow which
carbons are sp hybridized ( 1 mark ); Which carbons are sp 2 hybridized ( 1 mark )?
H
H 1
2
3
4
5
sp
sp 2-pentyne
sp2
sp2
( E )-3-heptene
1
2
3 4
5
6
7
2a . (1) Draw the Newman projection of the staggered conformation of propane.
H
H
H
H
H
H
H H
H H
2b . (1) Hexane and water are immiscible. Which solvent has a higher density? Water
3a . (8) Show the reagents required to execute the reactions shown below.
CH
3
CH
3
O
O
CCl
3
CCl
3
H
2
/ Pt or Pd
Cl
2
h ν
H+ H2O
MCPBA
3b . (8) Show the starting material required to yield the product shown below.
KMnO
4
1. BH
3
O
OH HO
HO
2
O
3
, Zn
2. Oxid. wrkup
,
-
OH
Li, NH
3

Chemistry 2203/7 (’07) TEST 1A Page 2/2
3c . (8) Show the expected product(s) for each of the reactions shown below.
MCPBA
H
2
O, H
+
H
2
, Lindlar catalyst
Br
2
, H
2
O
OH
O
Br
HO
4a . (6) MECHANISM. Draw a mechanism for the following reaction, showing all intermediates (