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Universiti Pendidikan Sultan Idris Mid-Term Test SEMESTER 1 SESSION 2020/2021

1. This document is the mid-term test for a basic organic chemistry course taken place on November 27, 2020. It contains 4 questions to be answered in 1 hour and 30 minutes. The test contains structural and reaction problems involving organic compounds. 2. Question 1 involves drawing molecular, skeletal, and condensed formulas for an organic compound, as well as drawing resonance structures. Question 2 involves drawing structural isomers, Newman projections, Sawhorse projections for alkyl substituted alkanes. 3. Question 3 involves identifying chiral centers, drawing Fischer projections, and enantiomers/diastereomers for chiral compounds. Question 4 involves drawing structural formulas and writing IUPAC nomenclature.

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rusnah chung
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289 views

Universiti Pendidikan Sultan Idris Mid-Term Test SEMESTER 1 SESSION 2020/2021

1. This document is the mid-term test for a basic organic chemistry course taken place on November 27, 2020. It contains 4 questions to be answered in 1 hour and 30 minutes. The test contains structural and reaction problems involving organic compounds. 2. Question 1 involves drawing molecular, skeletal, and condensed formulas for an organic compound, as well as drawing resonance structures. Question 2 involves drawing structural isomers, Newman projections, Sawhorse projections for alkyl substituted alkanes. 3. Question 3 involves identifying chiral centers, drawing Fischer projections, and enantiomers/diastereomers for chiral compounds. Question 4 involves drawing structural formulas and writing IUPAC nomenclature.

Uploaded by

rusnah chung
Copyright
© © All Rights Reserved
Available Formats
Download as PDF, TXT or read online on Scribd
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CONFIDENTIAL

UNIVERSITI PENDIDIKAN SULTAN IDRIS

MID-TERM TEST
SEMESTER 1 SESSION 2020/2021

COURSE : SKO3013 COURSE : BASIC ORGANIC CHEMISTRY

DATE : 27 NOV 2020 DURATION : 1 HOUR 30 MINUTES

INSTRUCTIONS
1. This question paper contains FOUR questions.
2. Answer ALL questions.
3. Please DO NOT use pencil.

This question paper contains 3 pages including the cover page

NAME QUESTION MARK

MATRIC NUMBER GROUP


2

3
LECTURER
4
DR. WAN MOHD NUZUL HAKIMI W SALLEH
TOTAL / 40

DO NOT OPEN THIS QUESTION PAPER UNTIL


YOU ARE TOLD TO DO SO

CONFIDENTIAL
SKO3013 Basic Organic Chemistry 2

ANSWER ALL QUESTIONS

1. (a) Based on the structure below, answer the following questions.

H H O
H C C C N H
H
(i) Determine their molecular formula.

(iii) Draw their skeletal formula.

(iii) Draw their condensed formula.


[3 Marks]

(b) Based on the structure below, draw their resonance structures.

(i)

N
(ii) H
[4 Marks]

2. (a) Draw the four possible structural isomers of C4H8.


[4 Marks]

(b) Draw Newman projections of 2,3-dimethylbutane through C2-C3 bond in


eclipsed conformation.
[2 Marks]

(c) Draw Newman projections of 1-chloro-2-methylbutane through C2-C3 bond in


staggered conformation.
[2 Marks]

(c) Draw Sawhorse projections of 2-methylpropane through C1-C2 bond in


eclipsed conformation
[2 Marks]

(d) Draw Sawhorse projections of 1-bromo-2-methylpropane through C1-C2 bond in


staggered conformation.
[2 Marks]

[See next page


SKO3013 Basic Organic Chemistry 3

3. (a) Suggest one example of chiral compounds that have 2 chiral centers and identify
their chiral centers.
[2 Marks]

(b) Convert the following formulas to Fisher projection and determine their R or S
configuration.

CH3 COOH

H CH2CH3 CH3
(i) Cl (ii) H OH
[4 Marks]

(c) Draw the Fisher projection for 3R-chloro-2S-pentanol.


[2 Marks]

(d) Draw the skeletal formula of your answer at 3. (c) by using wedge and line.

[2 Marks]
(e) Draw their enantiomers and diastereomers.

[4 Marks]

4. (a) Draw the structural formulas for each of the following compounds.

(i) Neopentyl bromide

(ii) 1-chloro-2-isobutylcyclopentane

(iii) 1,3-cyclohexanediol
[3 Marks]

(b) Write the IUPAC nomenclature for each of the following compounds.

(i) (ii)
OH
HO OH

(iii) (iv)
I

[4 Marks]

[See next page

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