Beruflich Dokumente
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DEPARTMENT OF CHEMISTRY
INSTRUCTIONS TO INVIGILATORS
Provide each candidate with two plain papers for rough work.
INSTRUCTIONS TO CANDIDATES:
1
Organic Chemistry Major Test 1 (CHM 201M & MCHA 021 ) 23 March, 2015
QUESTION 1 [9]
Use examples to clearly illustrate the meaning of the following terms and expression.
2
Organic Chemistry Major Test 1 (CHM 201M & MCHA 021 ) 23 March, 2015
QUESTION 2 [9]
(a) Methoxyethane and propanol have comparable molecular weights but different
boiling points.
O OH
methoxyethane propanol
bp = 8oC bp = 97oC
O HO H H OH
NaBH4, H3O+
+
50% 50%
3
Organic Chemistry Major Test 1 (CHM 201M & MCHA 021 ) 23 March, 2015
QUESTION 3 [15]
Draw the structural formulae or give the IUPAC name of each of the following
(b)
CHO
COOH
(c) 3,5-dioxohexanoate
(d) (S)-2-hydroxypropanal
(e)
CN
(f)
O O
4
Organic Chemistry Major Test 1 (CHM 201M & MCHA 021 ) 23 March, 2015
QUESTION 4 [15]
Give the products, the missing starting material OR reagents of the following reactions
(a) (2)
PCC
OH
CH2Cl2
(b) (2)
O H3O+
+ NH2
(c) (4)
O O
O
H2O
A + B
(d) (2)
N DIBAL-H,toluene, -78
C
H3O+
5
Organic Chemistry Major Test 1 (CHM 201M & MCHA 021 ) 23 March, 2015
(e) (2)
O (CH3)2CuLi, ether
Cl
(f) (3)
OH Heat
OH
QUESTION 5 [16]
CH CH CH CH(NH )COOH
3 2 2 2
F Br Br
H and
H F
6
Organic Chemistry Major Test 1 (CHM 201M & MCHA 021 ) 23 March, 2015
(c)
(i) What is the maximum number of stereoisomers possible for this compound?
CH3CH(OH)CH(OH)CH2CH3
QUESTION 6 [30]
(a) Use Wittig reaction to synthesize the alkene shown below: (6)
7
Organic Chemistry Major Test 1 (CHM 201M & MCHA 021 ) 23 March, 2015
(b) Propose efficient syntheses of the target molecule below starting from a cyclic
alkene. Be sure to show all intermediate products and reagent conditions needed for
each step. (6)
O
Cl
Cl
O
(c) Using benzene as your starting material, show how would you prepare the
amide below? (6)
8
Organic Chemistry Major Test 1 (CHM 201M & MCHA 021 ) 23 March, 2015
(d) Propose efficient syntheses of the target alcohols below. Be sure to show all
intermediate products and reagent conditions needed for each step. (Hint: Grignard
reagent should be used in one of the steps for both alcohol.
(i) (6)
OH
(ii) [6]
OH
O
9
Organic Chemistry Major Test 1 (CHM 201M & MCHA 021 ) 23 March, 2015
QUESTION 7
[16]
(a) Propyl ethanoate is an ester responsible for the smell of pears, how would you
prepare propyl ethanoate using an alcohol and an appropriate acid. Be sure you show
how you arrived at your answer (show detailed mechanism). (8).
(b) Cyclic hemiacetals containing six-membered rings are stable compounds that are
readily isolated, show using a detailed mechanism how you would prepare the
hemiacetal below: [8]
OH
10