Organic Chemistry Test Paper for Final Examination

(2023/01)

Name： Student No.：

No. 1 2 3 4 5 6 7 8 Total

Score

1. Give IUPAC names to the following compounds: (12%)

CH3 Br H3C H3C CH2CH2CH3
a) b) c)
H CH3
CH3CHCH2CH2CHCH3
H
H H

C2H5 OH
d) CH(CH3)2 e) f)
C
H 3C
Cl OH
H

2. Draw structures corresponding to the following IUPAC names: (8%)

(a) 3-Bromo-2-nitrophenol (b) 4-Bromo-1-hexyne

(c) p-Nitroaniline (d) Allyl alcohol

3. Predict the major product(s) of the following reactions: (15%)

(CH3)3CCl CH3CH2Cl
(1)
AlCl3 AlCl3

KMnO4
H2SO4/H2O

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4. True-false choice questions (Write “T” for true and “F” for false): (10 %)
(1) ( ) Meso compound is a pure compound.
(2) ( ) Lewis acid can release hydrogen ion(s).
(3) ( ) A molecule is aromatic if it contains a total of 4n+2 π electrons.
(4) ( ) A group of molecules have the general formula of CnH2n, so they must
be alkenes.
(5) ( ) In SN2 reaction, the central carbon underwent Walden inversion.
(6) ( ) Free radical reaction includes three stages: chain initiation, chain
propagation and chain termination.
(7) ( ) In the electrophilic substitution reactions of aromatic rings, the
carbocation intermediate is not aromatic.
(8) ( ) Optically active molecules are always chiral molecules.
(9) ( ) The sulfonation reaction of benzene is reversible.
(10) ( ) Grignard reagents are strong electrophiles.

5. Short answer questions: (20%)

(1) Order each of the following compounds with respect to SN2 reactivity. (3%)

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(2) Convert the following tetrahedral representation of (R)-2-Bromobutane into a
Fischer projection. (3%)

(3) Rank the following substituted phenols in order of increasing acidity. (4%)
OH OH OH OH

NO2 OCH3 Br

(a) (b) (c) (d)

(4) How would you distinguish between the following compounds using simple chemical
tests? Tell what you would do and what you would see. (5%)

(5) How would you distinguish the following compounds using simple chemical tests? Tell
what you would do and what you would see. (5%)

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6. Propose reasonable mechanisms to the following reactions: (5%)

7. Synthesize the following target molecules from corresponding starting organic

compounds and any inorganic compounds you need. (20%)

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8. Structure determination: (10%)
(1) An unknown hydrocarbon A, with formula C6H12, reacts with 1 molar
equivalent of H2 over a palladium catalyst. Hydrocarbon A also reacts with OsO4
to give a diol, B. When oxidized with KMnO4 in hot acidic solution, A gives two
fragments. One fragment is a ketone, CH3COCH3 (acetone), and the other
fragment is a carboxylic acid, C. Write all reactions and show the structures of A,
B and C. (6%)

(2) Propose structures for compounds with the following formulas that give
a single monochloro product by radical chlorination. (4%)
(a) C5H12 (b) C4H8O2