CHEM 120R / 2012
Organic Chemistry Tutorial 4
School of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus
Chemical Reactivity - CHEM120R
ORGANIC REACTIONS
1.
Draw out and name the 9 possible products when ethane is reacted with excess bromine,
Br2, under ultraviolet light.
Br2
UV
CH3CH3
2.
Fill in the starting material required for each of the following alkene syntheses:
a)
H
H
C C
CH3
CH2CH3
H2/Pt
Lindlars
catalyst
b)
KOH
c)
H2SO4
CH2=CHCH2CH3
(minor product)
3.
Propose structures for alkenes that, on ozonolysis, yield:
a)
b)
O
H
C
O
H
H
C
O
CH2CH3
H
c)
C
CH(CH3)2
d)
O
O
CH3
4.
C
O
(CH2)4
C
H
O
Which alkyl halide in each pair will react faster in a nucleophilic substitution reaction with
NaOH? Justify your answer.
a)
5.
CH3Cl or (CH3)3CCl (SN1)
b)
1-bromohexane or 2-bromohexane (SN2)
How might you prepare these molecules using nucleophilic substitution reaction at some
step?
a)
CH3OC(CH3)3
b)
Page 1 of 2
CH3CH2CH2CN
CHEM 120R / 2012
6.
Organic Chemistry Tutorial 4
What products would you expect from the reaction of 1-bromopropane with these
reagents?
a)
7.
NaCN
b)
NaOCH3
c)
NH3
Propose a structure for an alkyl halide that gives (Z)-2,3-dimethyl-3-hexene as the major
product on an elimination reaction.
8.
9.
Identify these reactions as SN1, SN2, E1, or E2, and give the mechanism.

a)
CH3CH2CH(Br)CH3 + KOH
CH3CH2CH=CH2
b)
(CH3)3CCH(Br)CH3 + CH3OH/heat  (CH3)3CCH(OCH3)CH3
Complete the following reactions by filling in the missing organic products:
a)
b)
CH3
+
HCl
CH3CH=C(CH3)2
CrO3/H
CH3CHCHCH2CH3
OH
c)
CH3
e)
d)
1. O3
2. (CH3)2S
g)
CH3
f)
H
H 2O/H
CH2CH2CH3
CH3
C C
CH 3OH
H
h)
CH3
CH3CHCHCH2CH3
CH3
C C
Br
CHCH3
H
H2SO4
H 2 /Pt
CH3
O
CH3CH2CH2C OH
o
180 C
LiAlH4
OH
i)
CH3
C C H
H2
Lindlar's cat.
j)
CH3
CH3CH2
C Cl
CH3
10.
Devise reaction schemes for each of the following syntheses:
a)
Propane from 2-propanol (2 steps)
b)
Ethanamide from Ethanol (3 steps)
c)
Acetic acid from 2-bromobutane (4 steps)
d)
Formaldehyde from Bromoethane (2 steps)
e)
Ethyl ethanoate from ethane (7 steps)
Page 2 of 2
NH 3
Ethanol
+