Sally Fitzgibbons Foundation

Beginning the Academic Essay

1

Surname and Initials
Student Number 45

Organic Chemistry II (AAOCH2A/AAOCA2B/AAOCC2B) 20 October 2017
Test 3

QUESTION 1 5
Select the correct answer to each question from 1.1 to 1.5 and write the corresponding letter in
the block at the end of each question.

1.1 Which of the following transformations represents a reduction reaction:

1.2 Identify the reagents that you would need to accomplish the following transformation:

A 1) H3O+, heat 2) CrO3, acidic medium
B 1) SOCl2, pyridine 2) CH3CH2OH 3) Na2Cr2O7, acidic medium
C 1) CH3CH2MgBr 2) H2O 3) Na2Cr2O7, acidic medium
B 1) LiAlH4, ether 2) H3O+ 3) CH3CH2OH

1.3 Treatment of the following compound with NaBH4 will result in the formation of
cyclohexanol:

1.4 Choose the correct reagents to give the following transformation:

A 1) SO3 2) H2SO4
B 1) HNO3/H2SO4 2) SnCl2/H3O+ 3) NaOH
C 1) CH3CH2Cl/AlCl3 2) KMnO4/H3O+
D 1) Br2/FeBr3 2) KMnO4/H3O+ 3) NaOH

1.5 Which of the following aromatic compounds will contain 7 carbon atoms?

A toluene B phenol C o-xylene D aniline O
O
O
A
B
C
D CH3CH2CHOCH3CH2CCH2CH3
O CHOOCNH2
O
COOHABCD NH2

2

QUESTION 2 8
2.1 Give the systematic IUPAC names of the following organic compounds:
2.1.1
______________________________________ (1)
2.1.2 (remember stereoisomerism!!)

______________________________________
(1)
2.1.3

______________________________________ (1)
2.1.4

______________________________________ (1)
2.1.5

____________________________________
(1)
2.1.6
_____________________________________ (1)
2.1.7

_____________________________________ (1)
2.1.8
_____________________________________
(1) H3CBr HOH
HOH BrBrOH OH OH HOCH2CHCH2OH
OH C
O
H OH

3

QUESTION 3 10
Identify the reagents necessary to accomplish each of the following transformations:

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

(i)

(j)

QUESTION 4 8

4.1 During the monochlorination of methane a free-radical mechanism is used. A free-radical
mechanism always involves THREE steps. State the three steps and write reaction
equations to indicate them. (12 x ½) (6)

(g)
(h)
(i)
(j)
COH
O
SO3H
acetophenone
chlorobenzene
(a)
(b)
(c)(d)(e)(f)

4

4.2 This is not a very good method of preparing an alkylhalide. Briefly explain why.

(2)

QUESTION 5 5
For each of the following (5.1-5.5), select the BEST method to produce the required
product. Draw a circle around the method that you will select.
5.1

5.2

5.3

5.4

5.5

OH
H2O
Hg(OAc)2
NaBH4
BH3
THF
H2O2
NaOH I
O
O
AcOOAc
OAc
CH3CH2CH2OH
CrO3/H3O+
CH3CH2COOH CH3CCCH3
H2
Lindlar catalyst
Na
NH3
H3C
CC
H
CH3
H OH
OH
KMnO4/H3O+
KMnO4/OH- CH3CCH2CH2COOH
O
CH3CHCH2CH2COOH
OHNaBH4
ethanol
H3O+
LiAlH4
ether
H3O+

5

QUESTION 6 5

Provide the products of the following reactions:
6.1

6.2

6.3

6.4

6.5

QUESTION 7 9

Each of the following syntheses requires more than one step. How would you carry them
out?

7.1
(5)

7.2
(4)

CH3CHCH2Cl
CH3Mg
ether O
CH3MgBrH2O CH3CCH3
OPCC CH3CCCH2CH3
O3Zn/H+ CH3CH2CH2COH
ONaBH4
Ethanol
H3O+ HCCHCH3CH2CH2CHCH3
OH H3COHCH3

6

TOTAL: 50
FULL MARKS: 45

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