UNIVERSITI TUNKU ABDUL RAHMAN

ACADEMIC YEAR 2019/2020

JANUARY 2020 TRIMESTER

FINAL ASSESMENT

UDEC2104 ORGANIC CHEMISTRY II

DATE & TIME OF DOWNLOAD: 9:00 AM, 14TH MAY 2020

DATE & TIME OF SUBMISSION: 11:00 AM, 14TH MAY 2020

DURATION: 2 HOURS

BACHELOR OF SCIENCE (HONS) CHEMISTRY

Instructions to Students:

General

1. This Final Assessment (FA) is an Individual, Open-Book assessment which consists of

FOUR (4) questions. Each question carries 25 marks.

2. You are required to answer ALL questions, and submit the ANSWER SCRIPT by
11:00 am, 14th MAY 2020.

3. During the period of 2 hours of this FA, the examiner(s) can be reached at
(a). Microsoft Teams with Code : sqaflnz, or
(b). Email: [email protected]
You may use the above e-platform(s) to check with the examiner(s) if you need any
clarification on this FA question paper.

4. You may refer to any books, lecture notes, published materials, online resources etc.
when answering the questions. Proper referencing is necessary to avoid plagiarism.
However, Copy-and-Paste, Consultation, Discussion and Sharing of Answers are
STRICTLY PROHIBITED in this FA.

This question paper consists of 4 questions on 7 printed pages.

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UDEC2104 ORGANIC CHEMISTRY II

Q1. (a) (i) Indicate each asymmetric carbon in the following compound with an
asterisk (*).

(3 marks)

(ii) How many stereoisomers are possible for the above compound?
(1 mark)

(b) Rank the following substituents in order of increasing priority using the Cahn-
Ingold-Prelog convention. (3 marks)

-(CH3)C=CH2, -CH=CH2, -N(CH3)2 -CH2CCH, -CH2C(CH3)3

(c) Give the IUPAC name for the following compound, including the (R) or (S)
designation.

(3 marks)

(d) Convert the following perspective formula to Fischer projection.

(3 marks)

This question paper consists of 4 questions on 7 printed pages.

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UDEC2104 ORGANIC CHEMISTRY II

Q1.(Continued)

(e) Indicate the stereochemical relationship in each of the following pairs of

compounds. For example, enantiomers.

(i)

(1 mark)

(ii)
H H

CH3 CH3
CH3 H

H CH3
(1 mark)

(iii)

(1 mark)

(f) Define each of the following terms:

(i) Optically active (2 marks)

(ii) Chirality (2 marks)

(g) A sample of 2-methyl-1-butanol has a specific rotation, [α ]25

D , equal to +1.151°.

(i) Calculate the enantiomeric excess (e.e.) of the sample. Given that the
(S) isomer has a specific rotation of -5.756°. (2 marks)

(ii) Calculate the percentage of each enantiomer present in the sample.

(3 marks)
[Total : 25 marks]

This question paper consists of 4 questions on 7 printed pages.

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UDEC2104 ORGANIC CHEMISTRY II

Q2. (a) (i) Draw both chair conformations of the following tri-substituted
cyclohexane. Indicate all the 1,3-diaxial interactions present in the chair
conformers drawn.
CN
CH3

H3C
(3 marks)

(ii) Indicate the more stable conformation. (1 mark)

(iii) One conformation is more stable than the other by 0.4 kcal/mol.
Calculate the energy cost of a 1,3-diaxial interaction for CN/H.
(2 marks)

(b) (i) Draw Newman projection for all the six possible conformations of 3-
chloro-4-methylhexane by looking down C3-C4 (i.e. C3 in the front)
bond. (Rotate front carbon only) (3 marks)

(ii) Using the table of strain energy below, calculate the total strain energy
for each of the staggered conformation drawn in (b)(i). Identify also the
MOST stable conformation. (4 marks)

Type of Interaction Strain Energy (kcal/mol)

CH3 and Cl gauche 0.4
CH2CH3 and Cl gauche 0.7
CH3 and CH3 gauche 0.8
CH3 and CH2CH3 gauche 0.9
CH2CH3 and CH2CH3 gauche 1.1

(c) (i) The solvolysis reaction below is a substitution reaction. State the
expected mechanism (SN1 or SN2) for the following reaction:

(1 mark)

(ii) Write out the mechanism to account for the formation of the products.
(6 marks)

(iii) Which one is the major product? (1 mark)

This question paper consists of 4 questions on 7 printed pages.

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UDEC2104 ORGANIC CHEMISTRY II

Q2. (Continued)

(d) Explain why methyl chloride and neopentyl chloride could not undergo an E2
elimination reaction.

CH3Cl (CH3)3CCH2Cl
(methyl chloride) (neopentyl chloride)
(4 marks)
[Total : 25 marks]

Q3. (a) Explain why base-promoted chlorination and iodination of acetaldehyde occur
at the same rate. (3 marks)

(b) Show how you would accomplish the following syntheses:

(5 marks)

(5 marks)

(c) Rank the following compounds in order of increasing acidity:

O O O O O
CH3 C CH3 CH3 C OH CH3 C OCH3 CH3 C CH2 C CH3

(2 marks)

This question paper consists of 4 questions on 7 printed pages.

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UDEC2104 ORGANIC CHEMISTRY II

Q3. (Continued)

(d) Propose a mechanism for the crossed Claisen condensation between ethyl
acetate and ethylbenzoate:

O O
C OCH2CH3 + CH3 C OCH2CH3

1) NaOCH2CH3
2) H3O+

O O
C CH2 C OCH2CH3
(5 marks)

(e) Write a short note on the Michael addition. (3 marks)

(f) Give the major product of the following reaction:

(2 marks)
[Total : 25 marks]

Q4. (a) What is the difference between resonance and tautomerization? (4 marks)

(b) Explain why the methylene protons of the following ketone are more acidic than
the methyl protons.

CH3COCH2NO2 (4 marks)

This question paper consists of 4 questions on 7 printed pages.

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UDEC2104 ORGANIC CHEMISTRY II

Q4. (Continued)

(c) Propose a mechanism for the following Cannizzaro reaction:

(4 marks)

(d) Show how you would accomplish the following synthesis. You will need to use
a protecting group.

(4 marks)

(e) Provide a retrosynthetic analysis of the following compound.

(4 marks)

(f) Write a short note on the following reactions:

(i) Diels-Alder reaction (2.5 marks)

(ii) Wittig reaction (2.5 marks)

[Total : 25 marks]

____________________________________

This question paper consists of 4 questions on 7 printed pages.