Test 3c Solutions

8/10/2019 Test 3c Solutions

1/9

Organic Chemistry Optional

Test

3c

Apri 200B

1/

Provide a name for the following compounds: 5

marks

a)

1-1C H- 1L- B1A 1 2 - l3N o t-r7G

C1 I

:::

H c...

lfs

MElHyL 2 -

Bv1f37 JCllf

7

C

b

c)

d

e)

N - A H 1 L.

f tz.ofltN/h VlINE


2/9

2/

Devise a

simple

chemical or physical

test to

distinguish

among

the

following compounds.

Explain: 5

marks)

- 1

r2 j)

-OH

@ 3300

\ I

@c o 70

OH

3 ) 00

-I

@ -um. 5Yoo vr '

How could you selectively extract

compound

B

(above)

and

isolate

i t

as a

pure

compound? 3 marks)

u.5

J)tr'llufl7tJJN

o f CQKf., J ~ 7 f h

. . { . . ~ N

/I ( -;) vi Vo,J} )

-


3/9

3/

Define the following

terms:

(5 marks

a) isomer

b) sp2 carbon

c) quaternary

amine

d) condensation reaction

e) reduction reaction

4/

Provide the structures for

the

products of

the

following

reactions: (10 marks

.JI

(lc1..-

c l....

Ol

. y l

a)

0 3 c ~

InU3

1C Mt10 f

:

b)

C ? ~

a pt:J1 t-O

EXCb)

@-

Un

-o H

f h ~

CJ.Q.

L

k- JIA.

C7t.:o,.J

c)

-

4J

_

t .

vH

0

d

0

I

I i

c ~

H

(d Ltj~

CH fv1jBv

1 . ...-:

7

@:r W

. 1 00

11.-0,J

Cffj/

CH3


4/9

e)

oR

D

4

">

-t-I+w

0

c'1

MVNffJu-J

f)

~ N

2-Jh

;>

~ C I h N H 1

g)

sooni ,..)

CJ-Ig

ItMr104-

C

D-..H

h

~

uh.H

~ M 7 U i . J

h) 0

11

A

GJ C. NH

~ V

os, 7, "1 7 W J

i)

( 2- PfWf)IA.C7-V

f

I

~ N 4 3

~

j)

o

o

l

t

"

C

l J j

+

f![fG

o ~ c ~

t ~

[H?:>

~

.fn.It>57/J ,17I. )r


5/9

5/ You are now an experienced organic chemist in the lab, having

used a number of organic lab techniques. You are preparing an organic

compound by adding an acid chloride slowly to a solution containing an

alcohol

at room temperature. When

the

reaction is complete, you

extract

it

with

ethyl acetate, and

then

wash

the

extract

with

sodium

bicarbonate and water. The solvent is removed by distillation and the

resultant solid recrystallized from acetone. An IR

spectrum

is run to

identify the

product.

Describe the purpose of extracting, washing and recrystallizing

the

product. 8

marks


6/9

6/ Working

for

Dr. Buchner, you are synthesizing some critical

reaction

intermediates from common starting materials. Indicate how

you might

perform

the following

multistep

syntheses:

15

marks)

a)

b)

c)

QCL

- - -

lftfl

0 3

0

6

HtN

D CJt3

Co

-- :

Q

0

1 6

@J

COt

ll

ILM1u

4-

/ 2

~

fJr

[ 1-

~ ~ 3

C; u

H

ClI:

OC

H

2

N

h.

CLJ2

et

.....-:::

CL

d

I

\

c

/Uts

oH

H-t

[y

-@-?O

elf]

0

C () H


7/9

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)

LJ-.. S r

"2 b

Na CN

@ JCnL P t ~

1

~ H N

/IIQ.01 /

"'

-

~ I h L

L

0

, o ~


8/9

100

5D

I

o

400 0

DOD

IR\O(NutllfFl I -. 1

00

51

000

IDO

IDD

.

DO

O

2000 I Vl llun U I Ii -, I

. 00


9/9

/

100

90

80

70

O

S

l ST

40

30

20

10

0

4000

3000

2000

1500

1000

400

5.

tOOl UK 1000

.

Y[Nunef

lt 1

llliNrl

O

n o

00 0

OO

151

50

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Test 3c Solutions