Brian Dorich
Organic Chemistry
Quiz #7 – Due Monday March 8th at 6:00 pm
1. Using the IR shown below, propose a structure that has the molecular formula of C9H8O (Hint
look at all the major characteristics shown in the IR and put them together).
IR:
Proposed Structure:
O
2. Using curved arrow formalism, give the mechanism of action that accounts for each of the
following products. Show all details of the mechanism in single steps.
S
O
1. n-BuLi
2. (CH3)2CHCH2CH2OTs
3. Hg, HgCl2, H2O
S
CH3
H
CH3
Step 1:
S
S
H
H
+
+
C4H9Li
S
C4H10
S
:H
Step 2:
S
S
+
(CH3)2CHCH2CH2OTs
:H
S
S
H
CH2CH2CH(CH3)2
Step 3:
O
Hg, HgCl, H2O
S
S
H
CH2CH2CH(CH3)2
H
CH3
CH3
3. Which of the following describes the synthesis of an aldehyde?
A. hydrogenation of an acid chloride using Pd/BaSO4/S as a poisoned catalyst.
B. reaction of a primary alcohol with Na2Cr2O7 in H2SO4.
C. reaction of a ketone with ozone.
D. treatment of a terminal alkene with Sia2BH
E. none of the above
Correct Answer: A.
4. Consider the equilibrium of each of the carbonyl compounds with HCN to produce
cyanohydrins. Which is the correct ranking of compounds in order of increasing Keq for this
equilibrium.
A.
B.
C.
D.
E.
H2CO<cyclohexanone<CH3CHO<2-methylcyclohexanone
CH3CHO<2-methylcyclohexanone<cyclohexanone<H2CO
cyclohexanone<2-methylcyclohexanone<H2CO<CH3CHO
cyclohexanone<2-methylcyclohexanone<CH3CHO<H2CO
2-methylcyclohexanone<cyclohexanone<CH3CHO<H2CO
Correct Answer: E.
5. Devise an efficient method for preparing 1-pentanamine from but-1-ene.
H2N
Step 1:
BrH
Br
H2O2
Step 2:
-CN
Br
-CN
Step 3:
-CN
H2, Ni
H2N