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Br
CH2
Br
CH3
+
H
CH3
Br
Br
1
CH3
+
CH3
HBr
CH3
CH3
H
H
OH
IR @ 3550 cm1 means alcohol
2. The formulae show you what to do to form X - add two carbons - how about two SN2
displacements on methyl iodide? The only tricky thing is to recognize the Hofmann
elimination to give Q (not Saytzeff) that follows.
1. 2 Equivalents of CH3I
2. HO, heat
N
H
CH3
+
N
H3C
HO
H
repeat
SN2
H
+
N
X C10H22N+ I
H3C
N
CH3
Note Hofmann
elimination!
C10H21N
Q
(CH3)2N
CH3
3.
(a) Just count carbons
H3C
CH3
4
=
1 2
(H3C)3C
5
5
CH3
8
CH3
4
=
1 2
(H3C)3C
7
CH3
6
C(CH3)3
H3C
6
CH3
10
6
5
C(CH3)3
CH3
9
(b) You could count Hydrogens. At 25 C the diethyl compound is flipping and averaging
some hydrogens. The tert-butyl compound cannot ring flip and one counts several more
hydrogens. You could not count carbons. They both have six different carbons at 25 C.
1
H
2
3
H
H
H3
(D3C)3C
D
C(CD3)3
D
1
H
1
H
1
H
H
4 H
H
2
2
H
CD2CD3
CD2CD3
H
H 3
D3CD2C
D3CD2C
H6
H
H
1
CD2CD3
H
H
H
D3CD2C
H
H
H
H
2 H
2
Note that the static diethyl compound is not distinguishable from the tert-butyl compound
by hydrogen counting..
1
H
1
H
2
H
3
H
H 3
H
CD2CD3
H6
D3CD2C
D3CD2C
2
CD2CD3
H
4 H
4
(c) The cis (0) coupling constant will be larger than the trans (ca. 120) coupling
constant.
(d) you can't, unless you think of using an optically active solvent in which the two
enantiotopic ring hydrogens of the cis compound will give different signals. The two ring
hydrogens of the trans compound are homotopic and will of course appear as one signal.
Br2
Br
Cy
H
Br
Br2
Br
Br
Br
PhOCH3
H
Br
PhOCH3
OCH3
Br
+
Br
Br2
SN2
Cy
H
Br
A
Cy
Br
Br
H
(+)
(+)
B
(+)
OCH3
Br adds to top
lobe
OCH3
(+)
Br adds to
bottom lobe
Br
Br
Br
PhOCH3
H
Br
PhOCH3
5.
(a) H2/Pd
(b) 1. HBr
2. Li
3. H2O
(c) Br2/H2O
(d) 1. B2H6
2. HO /HOOH 3 HBr
6. Three dimensions are utterly essential here. In the trans starting material, there
is no CH bond in the proper position so that a 180 E2 is possible. Only the
SN2 is possible. Displacement from the rear gives the cis stereochemistry shown
H
Br
(CH3)3C
By contrast, in the cis compound, there are two CH bonds in the proper ideal
position for an E2 (arrows) and so there is lots of E2 reaction in competition with
the SN2.
Br
H
(CH3)3C
E2
H
H
(CH3)3C