UNIVERSITY OF BOTSWANA

Department of Chemistry

Introductory Organic Chemistry (CHE 232) TEST 1 Date: 20TH September 2007

Surname: ___________________ Initials _________ ID NO: _______________

Lab Group:

INSTRUCTIONS

Answer all questions. Your answers must be put only in the spaces provided. Where
boxes are provided, make sure that your answer is in the box. Anything outside the box
will not be marked.

MC 1 2 3 Total
 Section A

20 Multiple Choice Questions. Total marks = 50%

Circle the letter for the correct answer with ink.

1. Which of the given structures represents the most stable conformation of

1-tert-butyl-3-chlorocyclohexane?

2. The hybridizations of the two carbon atoms, X and Y, indicated in the

structure below are

a) sp2 and sp3

b) sp and sp3

c) sp and sp2
d) sp2 and sp2
3. Which of the following Newman projection formulas represents 2, 4-
dimethylhexane ?

4. Which of the following benzene derivatives will react with a mixture of

concentrated nitric acid and sulphuric acid most easily?

5. Which of the substituted cylohexanes is the most likely product from the given
reaction?
6. Which of the following statements is true about aromatic compounds?

a) Aromatic compounds are planar, cyclic and conjugated.

b) Aromatic compounds are unsaturated planar and circular.

c) Aromatic compounds are cyclic, planar and saturated.

d) Aromatic compounds are conjugated, cyclic and unstable.

7. Which of the given structures is the most likely major product from the Friedel- Craft
acylation reaction shown below?

8. Which of the following alkenes reacts fastest with HBr?

9. What is the systematic name of the following compound?

a) 3, 4-diethylcyclohexene

b) 2, 3-diethylcyclohexene

c) 5, 6- diethylcyclohexene

d) 4, 5- diethylcyclohexene

10. The most likely product of the following reaction will be

11. The most stable conformational structure of the product from the following reaction
will be

12. The systematic name of the product from the following reaction will be

a) 2- pentanol b) 1-pentanol c) 2,3- pentadiol d) 1,2- pentadiol

13. The final product of the following sequence of reactions will be

14. Which of the following compounds will be produced from the alkyne hydration
reaction shown below?
15. What is the IUPAC name of the following compound ?

a) trans-1-ethyl-3-tert-butylcyclopentane b) trans-1-tert-butyl-3-ethylcyclopentane

c) cis-1-tert-butyl-3-ethylcyclopentane d) cis-1-ethyl-3-tert-butylcyclopentane

16. Which is the best choice of reagents to achieve the following transformation?

a) Br2 / H2O b) 1) Br3 /2) H2O2/-OH

c) H2O / H2SO4 d) H2O / HgSO4

17) Which of the following structures is the most stable conformation of cis-4-tert-
butylcyclohexanol?
18. Which is the final product from the following sequence of reactions?

19) Which is the most likely major product in the following reaction?
20. Which is the reagent of choice to bring about the following reaction?

Section B

Attempt All Questions. All final Answers should be written in INK in the boxes
provided. Total Score 50%

Question One

a) Draw the structure of each of the following compounds according to the given names.
Inspect if the given name is correct. If the name is not correct, write what you think is
the correct name: ( 6 marks)
b) Draw the two chair conformational isomers of menthol, the structure shown, and
indicate the more stable conformation (4 marks)
Question Three

a) Write the full mechanism for the electrophilic addition reaction shown below.
Indicate the major and minor carbocations that give rise to the major and minor
products:. Show the flow of electrons with appropriate arrows. (8 marks)

b) The reaction of the hydrocarbon P, C12H24, with ozone followed by reduction with
zinc in acetic acid gives 2-hexanone. The same product is formed from the hydration
of 1- hexyne using aqueous acid in the presence of mercuric ion. By writing the full
reactions for the two given reactions draw the structure of hydrocarbon P. (4 marks)
c) Draw first the planar structure and then the most stable conformational structure of the
product from the hydrogenation of 1.2-dimethylcyclohexene. . (4 marks)
d) Draw the structure of the missing unsaturated hydrocarbon in each of the following
reactions. (4 marks)

Question Three

a) Classify the given substituents on the basis of their effect on the benzene molecule
towards Electrophilic substitution. (4 marks)
b) Write the full mechanism for the bromination of nitrobenzene, showing all the
relevant steps in the reaction. (6 marks)

c) Predict the major product in each of the following reactions. (4 marks0

d) Using benzene or toluene as the only aromatic starting material, devise a synthesis for
each of the following compounds: (6 marks)

i) 3-Bromoacetophenone and ii) 2-Chloro-4-nitrotoluene

END OF TEST