CHE 232 STRUCTURE AND SURVEY OF FUNCTIONAL GROUPS I

(0RGANIC CHEMISTRY)
QUESTIONS AND SOLUTIONS

Section A
ANSWER ALL QUESTIONS (each question is worth 2 marks)

1. For the following structure there are …….1……..2 and ……..3 carbons

A. 3, 4, 1
B. 3, 3, 2
C. 3, 2, 3
D. 2, 3, 3

2. What are the hybridizations of the carbons X, Y and Z?

A. sp3, sp, sp
B. sp2, sp, sp3
C. sp2, sp, sp
D. sp3, sp2, sp

3. How many sigma bonds are present in the following molecule?

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4. What is the IUPAC name of the following compound?

A. 3-Bromo-2-hydroxypentane B. 2-Hydroxy-3-bromopentane

C. 3-Bromopentan-2-ol D. 3-Bromopentan-4-ol

5. Which of the following alkanes will have the highest boiling point?

A. Pentane B. 2,2-dimethylbutane C. 2-methylpentane D. hexane

6. What is the molecular formula of a hydrocarbon that has one triple bond, two double
bonds, one ring and 32 carbon atoms?

A. C32H62
B. C32H60
C. C32H58
D. C32H56

7. The eclipsed conformation of n-butane viewed along the C2/C3 bond has high energies
because of:

A. Steric strain
B. Angle strain
C. Torsional strain
D. Both steric strain and torsional strain

8. Which of the following Newman projection formulas represents 2,5-dimethylhexane?

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9. Which of the following compounds can exist as cis-trans isomers?

A. I and II B. I and IV C. I and III D . II and III

10. How many monochlorination product(s) are possible in the reaction of the alkane shown
below with chlorine in the presence of light?

A.. 4 B. 5 C. 6 D. 7

11. According to the Cahn-Ingold-Prelog convention, which priority ranking is correct for the
following sets of groups?

A. NH2 > OCH3 >CH3 >H C. H > OCH3 >CH3 > NH2

B. OCH3 > NH2 > CH3 > H D. OCH3 > CH3 > NH2 > H

12. The bromination of cyclopentene gives:

A. cis-1,2-dibromocyclopentane
B. trans-1,2-dibromopentane
C. 1,1-dibromocyclopentane
D. trans-1,2-dibromocyclopentane

13. The relationship between the structures below is best described by which term?

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A. Tautomers
B. Resonance structures
C. Conformational isomers
D. Stereoiosmers

14. Which one of the following schemes showing the flow of electrons from reagent forming
products is not correct?

15. The following reaction occurs in the formation of chloroethane from ethane by its
reaction with chlorine in the presence of light. In which step does this reaction occur?

CH3CH3 + Cl CH3CH2 + HCl

A. Initiation
B. Propagation
C. Termination
D. Both Termination and Initiation

16. Hydrogenation of 1,2-dimethylcyclohexene in the presence of a platinum catalyst will

A. Trans-1,2-dimethylcyclohexane
B. Cis-1,2-dimethylcyclohexane

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C. 1,2-Dimethylhexane
D. 1,3-Dimethylhexane

17. Which of the following reagents will NOT yield the given product in the reaction shown
below?

18. Addition of one equivalent of HBr to but-2-yne will produce

A. 2,2-dibromobutane
B. cis-2-bromobut-2-ene
C. trans-2-bromobut-2-ene
D. cis and trans-2-bromobut-2-ene
19. Which one of the hydrogen atoms in the following compound is most acidic?

A. Hydrogen atom attached to C-1

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SECTION B
EACH QUESTION IS WORTH 20 MARKS. ANSWER ALL QUESTIONS

Question 1

(i) Give the systematic names for the following compounds. Include stereochemistry
where applicable. [6 marks]

(ii) Draw the structures of compounds corresponding to the following systematic names.
[4 marks]
a. 4-Hydroxy-2-methylpentanoic acid

…………………………………………………………………………………………

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b. 7-Methyloct-1-en-4-yne

………………………………………………………………………………………..

(iii) Assign E and Z configuration for the compounds shown below. [8 marks]

(iv) Write a balanced equation for the complete combustion of n-butane. [2 marks]

Question Two

(i) For rotation about C1-C2 bond of 2,2-dimethylpropane draw the Newman projections
of the staggered and eclipsed conformations. [4 marks] [hint: there is only one of
each]

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(ii) Give the product for the reaction below and hence draw the chair conformations of
the product indicating the most stable conformational structure. [4 marks]

(iii) Give the structures of the alkenes that will yield the indicated products in each of the
following reactions. [6
marks]

(iv) Give the structures of the major products in each of the following reactions. [6
marks]

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Question Three

(i) Draw proper curved arrows to complete the reaction mechanism shown below and
give structures of two possible termination products. [6 marks]

Structures of two termination products: Combination of any two radicals

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(ii) Give the structures of the missing products or reagents in the reaction scheme shown
below.[10 marks]

(iii) An alkyne with molecular formula C5H8 is treated with excess HBr and two different
products are obtained each of which has molecular formula C5H10Br2.
(a) Give the structure of the starting alkyne.

…………………………………………………………………[1 mark]

(b) Give the structures of the two products.

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……………………………………………………………….[3 marks]

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