DEPARTMENT OF CHEMISTRY AND CHEMICAL TECHNOLOGY
ORGANIC CHEMISTRY I-202-BZF-05
Instructors: I. Dionne, R. Iyengar, B. Laquoc
1. ehxiasminbonkolnttains 13 questions and 12 pages. It is your responsibility to
check that there are no pages missing.
2. Fill in your name before answering the questions.
3. Answer ALL questions in thespace provided.
4. Ansqheertnns ink or ball point
5. Write CLEARLY, messy answers will not be marked.
6. Do not detach any of the sheets in this booklet.
7. Use the examination booklet provided for your rough work only and hand this in
also. Your instructor will not grade answers in the booklet.
8. Please note that NON-PROGRAMMABLE CALCULATORS and MOLECULAR
MODELS are permitted but cannot be passed around.
9. Whenever required, structural formulae must be shown complete. Free bonds, carbon
skeletal structures will be considered incorrect (except in ring structures).
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5. /10 6. /5 7. /6 8. /12
9. /13 10. /4 11. /20 12. /10
TOTAL /120 TOTAL /40 2
1. (a) The following compound has two isomers:
One isomer has a dipole moment of 0 D and the other has a dipole moment of 2.95 D. Propose
structures for the two isomers that are consistent with these data and give IUPAC names.
(b) Give the hybridization of all the C atoms in the following molecule. (3 Marks)
H 2 CHC CCH 3
(c) Predict the indicated bond angles in the following compounds: (3 Marks)
(i) The H-C-H bond angle in H 2=O
(ii) The C-N-H bond angle in (CH 3 2H
(iii) The C-O-H bond angle in CH 3H
2. (a) Which of the following compounds are Lewis acids? Explain. (2 Marks)
(i) (CH ) B
(ii) :CH 2
(iii) (CH )3 3 +
(b) Supply the curved arrows necessary for the following reaction and indicate the acid, base,
:OH H OH ..
H CCC H HOH + H CCC H H O :
2 3 + .. 3 3 + 2 3
(c) 1-oentene has a boiling point of 30 C, will the boiling point of 1-hexene be higher or lower than
(d) Which compound will have a higher boiling point? Explain (2 Marks)
or NCH 3
3. (a) Write bond-line formula for a primary, secondary and tertiary alcohol with the
molecular formula C H4O10Mar(k 3s)
(b) Write Newman projection formula for the most stable and least stable conformational isomers of
4. Provide IUPAC names or structures for the following compounds. (14 Marks)
(a) (CH ) CCH CH CH CH(CH )
3 3 2 2 2 3 2
(f) NO 2
(g) 4(2-2,,4-Hexadiene 5
5. Consider 2,3-dibromobutane:
(a) Draw Fischer projection formulas of all isomers. (3 Marks)
(b) Determine the absolute configuration (R or S) of each stereogenic centre.(3 Marks)
(c) Identify the relationship (enantiomers, diastereomers) between all pairs of molecules. (2 Marks)
(e) Which pair(s) of compounds can form a racemic mixture? (1 Mark) 6
6. Consider cis-1-bromo-2-chlorocyclohexane:
(a) Draw the most stable conformational structure for it and that for its mirror i(2 Marks)
(d) What is the stereochemical relationship between them? (1 Mark)
7. (A) WhiSch N2 reaction of each pair would take place more rapidly in protic solvent?
(i) CH B3 + SH
CH 3Br + H 2S