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Organic Chemistry I

1/

Optional Test 3a

Provide a name for the following compounds: (5 marks)

a)

b)

c)

c..1I;tC#3

@- CH2. CH Clh 'IC cH3

o

d)

0"3 CI-f z: c. H- C

e)

April 2008

CH3 Gil. CH
I

UIJ

cJ.h..

?'o

'H

~H

N < , I

Vf-f"3

2/
How would you use solubility tests to distinguish among the
following compounds: (5 marks)

aC'O"H

GfCl-l3
I......:;

N~111 fI.frL

"Nl-Q.
,--
r:
0

fru01L

- NiX'J ffJ1.,fht

- $oU-u5 t-f I rJ
- /fV5uw!> L
IN/'M
J)/lM.'1t3 I3lt3e

r,...-::

"~c.

LItIt"'th:0'i

fh~PJ C-

~5 U"U f !> t
IN

[[d0~

DIUA?t3

/luo

- ScM~6Lf. nJ
07t..16 $tE

How could you selectively extract compound B (above) and isolate it

as a pure compound? (3 marks)
- c;xIMC! Vl/J7tI DIfAA. 'rE rYf5

(0-

5V!.

Na OJr)

- !tUoJP</ '1Hi3 C!- tMcl '70 ffl,l(P.7?~ '/f{E

clttO.. t xYuc .

frut'

3/

Define the following terms: (5 marks)

a)

resonance structure

b)

sp3 carbon

c)

tertiary alcohol

d)

hydrolysis

e)

addition reaction

4/
Provide the structures for the products of the following
reactions: (10 marks)

a)

oH

b)

IiMno..t

I
"UI3
CffJ CH - C/1
'ut3

c)

ro

-7

Clf3

0
1/
I'" W~
C ~CH

' u+3

DH

d)

(L

JCJ
&

Ih

@:6

PI

R.tl>l"L cno N

oH

II

()YJ'I";)A1wN

- II

-t-

t+cN

()

Lt

C H
I C=,J

!to(J17t O,J

e)

f)

[H3

UI3

ort?u

It'lhl+4

Ctf3

(
~
~UhC-H-C ()H

hv;:Q

>

~'lhl-ht

C!f3
(

cH3 on: en (Jh. 0 H

">

CI1?>

g)

@-MjBY

-r

U~CHC0>
....14

--7

Uf3

01-/

cH3 U1- c.~H

~
~)

h)
't"

JhtJ-@

~ ()YlI'1\A'1t,cN

Cz
i)

j)
11"0

-0

f(4.:) ..a ns)

5/
You are now an experienced organic chemist in the lab, having
used a number of organic lab techniques. In an experiment you must
reflux your reaction mixture, extract the product, wash it free of an
acidic impurity, distill it and characterize it by IR spectroscopy .
Describe two of these techniques in more detail. (8 marks)

6/
Working for Dr. Emil S. Turf you are synthesizing some critical
reaction intermediates from common starting materials. Indicate how
you might perform the following multistep syntheses: (15 marks)
C>

01-/

C-H3 -c

a)

b)

II

~c,CJI

-1-1

19....J

UO#

C=N

CfO

Co)
---7

CfOH

}feN
~

0
c)

CH3

csrC--.:>H

[0)

I~

C/-b,o H
~

----)

l-J-T

C)tM()O~

11'6r

e)

6r

N H3

---="

OS

---1

I17rJ3

C$J
~

aN~

Cff3[,~

;]rC-O~
t;r

1'.:

d)

0
1/

II

...:,

/tJ 11 3

C~C~

YJC*3

7/
Predict the structures of the compounds indicated in the
question, provide the appropriate chemical reactions and interpret the
major peaks in the IR's provided. (10 marks)

"i -."

@ CfH12.0

--

LxHQNO

1000

"0

'000

100
90

80

c..:

70

60

50

%T

\'IIJ

OJ.J

40

30

C0 ev

20

v ~

10

0+----..-----.---------,----...----.....-.
4000

3000

'0

2000

1500

1000

400

O)~
raee

tool
,f:l'o'N untlfPI ...1

JOOO

,"0