Exam 3

Study Session (chp. 17, 18, t

emphasis on chp. 19)
whether each of the
1) State anti-aromatic,
or non-aromatic.
following are aromatic,

⑰
-

inste
as 9 -
Y
a)

Fin
e)

yw: E
f)
i t
is
R
X

2) Rate order of in EAS olp/m

in
increasing reactivity say-whether
+

effects would be observed. (1=most least

5=
directing
d)

* It -.-
al b) c)
-

3) Complete
the 17, 18]
sequences (chp.
ran

·
al
-

I:

:A-B duiFecl,
C)

1
 d)
Te
W - NazCreOz,
-

-: WBr
f)
NaOH,358
- 2) H30t

4) show complete rushing

a mechanism:

complete
5) the ran
sequences [chp. 19]
a) eof?
?
!
OH
I
b) OH
O
I

retent atte
Il
~

-y
C -
H

.. H
W H+
I

2
a)
, it
S

d xsCHzCzOH,
H2SO4

f) o HoXH #20
Il &
3
I H +
Ht

q) ⑧

Il N
NaC =
S
A HCl

n) il Ph3P=,
-

i)
?
N

?
(- MgBr)

Diss
j) I 03
- DMS

k) i NaBH4/
-H
Y
S
CH30H
3
 Fill the blanks in the ran
6) in
sequence:
O

11 NaC =
N LAH
S S
- HC1 (1) LiAIHY,
2) H,0t)

7)show mechanism for each

complete rushing
a

of the
following rens:
a) Imine Formation

~
II
I

1
- CH3 [HY,

3)Enamine Formation

8: CH3
11 [H+
- +
H
-
-
CH3
9

4
c)
Grignard ran

·O
Il ~MyBr
-H
I 2) Hyo+

8) Propose a
multi-stepsynthesis for the
following: NHz
as

mr

b)

9) Which aromatic
compound is more basic?Explain
using aromaticity.
-H

p I
as

3
10)
complete the
following rans:
19)
(Importantreme know for
to
chp.

a
D
~
NaCN MmyBr
~ H2C PPh3
=
HCl HzO+
2
iLiAIHy
2) H30+

I
nort ↑ -
NH,
3
Ht - I

~
oH
NH2

HOWIt Ht

I
h