Requirements for this paper:

Multiple-choice answer Non-programmable calculator: Open book examination?

NO YES NO
sheets:

Graph paper: Laptop:

NO NO

EXAMINATION: CLASS TEST 1 PROGRAMME: BSc

BEd

MODULE CODE: NCHM62310 DURATION: 90 mins

MODULE DESCRIPTION: ORGANIC CHEMISTRY MARKS: 41

EXAMINER(S): MS KV PHUNGULA DATE: 21 April 2021

TIME: 13h00

INSTRUCTIONS:

1. Read the instructions for each question very carefully before answering the
question.
2. Answer all questions and the paper has five questions
3. Use answer sheets provided
4. Molecular models are allowed
5. The used of a non-programmable calculator is allowed
6. The use of laptops,pencil, tippex and cellphones is not allowed
1. 436 Hz 1H NMR absorption was obtained on a spectrometer operating at 200 MHz
downfield from the TMS standard. Covert the Hz units to δ units.

Answer: 2.18
2. Assign priorities to the following set of compounds

-C≡CH, -CH(CH3)2, -NH2, -CH3

-NH2, -C≡CH, -CH(CH3)2, -CH3

3. Which of the following conjugated dienes will not react with dienophile in a Diels-Alder
reaction?

(a) A,B and D

(b) B, C and E

(c) A and C

(d) D, E and F

(e) All of the above

4.

(a) (2R, 3R,4R)-1,2,3,4,5- hydroxybutane.

(b) (1R, 2S, 3S,4R)-1,2,3,4,5-hydroxypentane.
(c) (1R,2R, 3S,4S)-butane-1,2,3,4,5-pentanol
(d) (2R, 3S,4S)-pentane-1,2,3,4,5-pentanol
5.
Answer A

Answer D

6. What is the reactive intermediate in the reaction of 1,3-diene with HCl, resulting in 1,4-
addition?
(a) Allylic radical
 (b) Dienophile
(c) Cyclic bromonium ion
(d) Allylic carbocation
7. Write down a complete IUPAC name of the following compounds.

8. How would you use the IR spectroscopy to distinguish the two compounds below?

The bot compounds will show a carbonyl group signal and around at 1735 wavelength. The
carboxylic acid will also an addition hydroxyl group signal at about 3400-3600 wavelength.
9. How would you use 1H NMR to distinguish the compounds?

The ester a singlet will be visible at around 2-2.5 and a second signal (a quartet) at
approximately 3.5ppm (between 3-4) and the last signal would be around 0.9-1 ppm
and it would be a triplet
The ketone also 3 signals are observed at 2-2.5 approximately 2.3 a singlet is visible
and also between 2-2.5 a quartet will be visible and around 09-1 ppm a triplet will be
visible.

10. How many signals would you expect each of the following molecules to have in its 1H and
13
C NMR spectra?
(a) 1H NMR - 2 signals
13C NMR - 4 signals
(b) 1H NMR - 2 signals
13 C NMR - 3 signals

11. Predict the splitting patterns you would expect for each proton in the following molecules.

(a) a- singlet
b- triplet
c- triplet
(b) a- singlet
b-doublet
c-triplet
d-triplet

12. Assume that you have a compound with formula C3H6O.

(a) How many double bonds and/or ring does your compound contain? one double
bond
(b) If the compound shows an infrared absorption peak at 1715 cm-1, what functional
group does it have? Ketone
(c) If the compound shows a singlet 1H NMR absorption peak at 2.1 δ, what is the
structure? Write down the IUPAC name. Propan-2-one

13. Can a conjugated diyne such as 1,3-butadiyne undergo Diels-Alder reaction with a
dienophile? Explain.
no only diene and dienophile can undergo Diels -alder reaction, alkyl of dienophile can
undergo reaction but not diyne
14. Chiral molecules are represented by:

(a) I, II, III, IV and V

(b) I, II, III, and IV
(c) I and IV
(d) V
15. Which structures(s) represent(s) diastereomer(s) of I
(a) II
(b) II and III
(c) II and IV
(d) II and IV
(e) II and IV
ooo00oo