Organic Chemistry Major Test 1 (CHM 201M & MCHA 021 ) 23 March, 2015

SEFAKO MAKGATHO HEALTH SCIENCES UNIVERSITY

MEDUNSA CAMPUS

FACULTY OF HEALTH SCIENCES

SCHOOL OF PATHOLOGY & PRECLINICAL SCIENCES

DEPARTMENT OF CHEMISTRY

BCur & BOH MAJOR TEST 1

MODULE: CHM 201M & MCHA 021 DATE : 23/03/2015

Organic Chemistry 2

STUDENT NAME………………………………….STUDENT No:……………………..

TIME: 2 HOURS 30 min PAPER : P1 OF 1

AVAILABLE MARKS: 110 FULL MARKS : 100

INTERNAL EXAMINER : DR RB MASEKO

THIS PAPER CONSISTS OF …10…PAGES EXCLUDING COVER PAGE

INSTRUCTIONS TO INVIGILATORS

Provide each candidate with two plain papers for rough work.

INSTRUCTIONS TO CANDIDATES:

1. Answer all questions in the spaces provided

2. Write neatly and legibly.

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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.

(a) Meso compound

(b) Salt of a carboxylic acid (name your salt).

(c) Constitutional isomers with different functional groups

(d) An alkene which does not show cis-trans isomerism

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Organic Chemistry Major Test 1 (CHM 201M & MCHA 021 ) 23 March, 2015

QUESTION 2 [9]

Give reasons that might help to explain the following observation.

(a) Methoxyethane and propanol have comparable molecular weights but different
boiling points.

O OH

methoxyethane propanol

bp = 8oC bp = 97oC

(b) A ketone is less reactive than an aldehyde towards nucleophilic attack.

(c) A racemic mixture is formed when the reaction below is performed:

O HO H H OH
NaBH4, H3O+
+

50% 50%

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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

(a) N-ethyl-N-methyl propylamine

(b)

CHO

COOH

(c) 3,5-dioxohexanoate

(d) (S)-2-hydroxypropanal

(e)

CN

(f)

O O

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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+

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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]

(a) Locate the stereogenic center and draw both enantiomers.

CH CH CH CH(NH )COOH
3 2 2 2

(b) Are the two molecules below enantiomers or identical?

F Br Br
H and
H F

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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

(ii) Draw all the pairs of diastereomers for the compound

QUESTION 6 [30]

(a) Use Wittig reaction to synthesize the alkene shown below: (6)

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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)

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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

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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

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