1)

1
(No Transcript)
2
(No Transcript)
3
(No Transcript)
4
(No Transcript)
5
(No Transcript)
6
(No Transcript)
7
(No Transcript)
8
1) Which of the following alkanes will give more
than one monochlorination product when treated
with chlorine and light? a)  2,2-dimethylpropane,
b) cyclopropnae, c) ethane, d)
2,3-dimethylbutane    
9
2) Which type of halogenation is most selective?
Bromination is most selective, always occurring
at the site of the most stable radical.
10
 3)  Which of the following absorbs at the
highest frequency? a) 1,3,5-hexatriene, b)
1,3,5,7-octatetraene, c) 1,7-diphenyl-1,3,5-heptat
iene, d) 1,6-diphenyl-1,3,5-heptatriene
11
4) Draw 3,5-difluoroanisole.
12
1  5) Circle each of the following compounds
that is aromatic.
4n 2 2 pi electrons
4n 2 10 pi electrons
13
1) 6) Which of the following compounds will
undergo Fredal-Crafts alkylation? a)     a)
benzoic acid, b) nitrobenzene, c) aniline, d)
toluene
14
7) Which of the following compounds is most
acidic?
15
8) Which of the following gives a secondary
alcohol when treated with methyl grignard? a)
butyl formate, b) 3-pentanone, c)pentanal, d)
methyl butanoate
16
(No Transcript)
17
9) Draw N-ethyl-N-propylformamide.
18
10) What does a positive iodoform test tell you
is present
It indicates the presence of a methyl ketone.
19
11)
12)
20
13)
14)
21
15)
16)
22
17)
18)
23
19)
20)
24
(No Transcript)
25
(No Transcript)
26
(No Transcript)
27
(No Transcript)
28
(No Transcript)
29
(No Transcript)
30
Molecular ion peak is a single peak at 164, so no
halogens or nitrogen.
31
164/12 13 x 12 156
164 156 8 hydrogens
C13H8
2(13) 2 8 20/2 10
C12H20
2(12) 2 20 6/2 3
C11H16O
2(11) 2 16 8/2 4
2(10) 2 12 10/2 5
C10H12O2
32
Looking at this you have sp2 and sp3 hydrogens as
well at a carbonyl.
33
You have 5 aromatic protons, so most likely a
benzene ring is present, so that takes 4 of your
five degrees of unsaturation. And the final
degree is taken by the carbonyl.
34
8 different types of carbon, 4 of those are taken
up by a monosubstituted benzene ring. You know
this because of the 4 peaks in the 120 to 140
range. And the fact that there are 5 aromati
protons.
35
So what is the substituent . We have 4 carbons
and 2 oxygens left, plus 7 hydrogens.
You know there is a carbonyl so that is one
carbon plus one oxygen. What is the other oxygen?
So it could either be an ether, an alcohol, or
part of an ester. We know it isnt an alcohol
b/c there is no large peak around 3400 in the IR.
So ester or ether?
36
This is not an ether b/c at least one of the
remaining 3 carbons would be a singlet somewhere
up field and that isnt present. So it must be
an ester.
37
So here are all the possible esters, which one is
it?
38
For the nonaromatic protons we see a triplet a
multiplet and a quartet, The multiplet tells you
that the three carbons are in a group together.
39
(No Transcript)