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UPSI Basic Organic Chemistry Test Paper

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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314 views3 pages

UPSI Basic Organic Chemistry Test Paper

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
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

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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