Final Organic Chemistry Exam

FINAL TEST
CHM457: FUNDAMENTAL ORGANIC CHEMISTRY

Please answer ALL questions in PART A and PART B
NAME:----------------------------------------------------------------- ID:----------------------
GROUP:------------------
PART A (25 MARKS)
1. Choose the correct product for the following reaction?
A
B
C
D
2. Predict the product for the following reaction?
A.
B.
C.
D.
3. Why alkyl halides are considered to be very reactive compounds towards nucleophile?
A. They have an electrophilic carbon & a good leaving group

B. They have a nucleophilic carbon & a good leaving group
C. They have an electrophilic carbon
D. They have an electrophilic carbon & a bad leaving group
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4. Which of the following compounds should react with NaN3 via SN2 mechanisme?
A.
B.
C.
D.
5. Predict the product, if 3- bromo-4-methyl-pentane is treated with sodium ethoxide

(NaOCH3).
A.
B.
C.
D.
6. The following alkenes gives the same product upon reaction with hydrogen chloride
except
A. B.
C. D.
7. The reaction of but-1-yne with an excess of hydrogen chloride produce the following:
A. B.
C. D. CH3CH2CH2CHCl2
8. Determine which of the following equations does not show the correct main products?
A.
B.
C.
D.
9. Select the wrong statement about hydroboration of propene.
A. Addition of a B–H bond to the alkene is Markovnikov addition

B. Hydroboration followed by treatment with H2O2 gives propan-1-ol
C. BH3 acts as an electrophile
D. The alkene is an electron donor
10. The product formed in the reaction of propyne with dilute H2SO4 and HgSO4 is
A. Propyl hydrogen sulphate

B. Propanone
C. Propanal
D. Propanol
11. The reaction between an alcohol and a carboxylic acid yield:
A. a carboxylic acid
B. a chloroalkane
C. an ester
D. a salt
12. Which one of the following compounds is a secondary alcohol?
A. CH3CH2COCH3
B. CH3CH2CH(OH)CH3
C. CH3CH2CH2OH
D. CH3CH2C(CH3)2OH
13. Alcohols undergo many types of reactions. Which of the following reactions is NOT
undergone by the alcohol functional group?
A. Dehydration
B. Addition
C. Esterification
D. Substitution
14. Oxidation of a primary alcohol with PCC in dichloromethane will produce
A. a carboxylic acid
B. a secondary alcohol
C. an alkene
D. an aldehyde
15. In the conversion: butanol butene, the reagent used is
A. concentrated H2SO4
B. acidified KMnO4
C. concentrated HCl
D. aqueous NaOH
16. Which of the following is CORRECT about benzene?
A. The molecular formula is C6H5.

B. It has two double bonds in its molecule.
C. Benzene undergoes electrophilic substitution to sustain their aromaticity.
D. The word “benzyl” is used when benzene is considered as a substituent.
17. What is the name of the following compound?
A. 2,4-dichloro-6-ethyl-5-phenyl-3-heptene
B. 2,4-dichloro-6-methyl-5-phenyl-2-heptene
C. 2,4-dichloro-6-methyl-5-benzyl-3-heptene
D. 2,4-dichloro-6-ethyl-5-benzyl-2-heptene
18. Choose the CORRECT name for the following compound.
I. 2-bromo-4-ethylaniline II. 1-amino-2-bromo-4-ethylbenzene

III. 1-bromo-2 amino-5-ethylbenzene IV. 1-ethyl-3-bromo-4-aminobenzene
A. I and II
B. I and III
C. II and III
D. III and IV
Refer to the following reactions to answer question 19 and 20.
19. Identify Compound Y and Reagent I in the above reaction.
Compound Y Reagent I
A. Nitrobenzene Cl2/CH2Cl2
B. Nitrobenzene Cl2/FeCl3
C. Benzenesulfonic acid Cl2/CH2Cl2
D. Benzenesulfonic acid Cl2/FeCl3
20. What is the product(s) form if Compound X is replaced by chlorobenzene?
I. 2-chloro-2-nitrobenzene II. meta-chloronitrobenzene

III. ortho-chloronitrobenzene IV. para-chloronitrobenzene
A. I and II
B. I and III
C. II and III
D. III and IV
21. Among the alkenes which one produces tertiary butyl alcohol on acid hydration?
A. (CH3)2C=CH2
B. CH3-CH=CH-CH3
C. CH3CH2CH=CH2
d) CH3CH=CH2
22. With respect to the electrophilic aromatic substitution of benzene which of the
following is not true:
A. A non-aromatic intermediate is formed

B. Benzene acts as an electrophile
C. A proton is lost in the final step
D. Resonance forms are important
23. Which alkyl halide has the highest reactivity for a particular alkyl
group?
A. R-F
B. R-Cl
C. R-Br
D. R-I
24. Identify the most stable carbocation.
A. (CH3)3C+
B. CH3CH2+
C. (CH3)2CH+
D. CH3+
25. Ethyne is also called as
A. acetylene
B. ethene
C. ethylene
D. acetic acid
PART B (35 MARKS)
Question 1
a) Name compound A
3,5,5-trimethyl-1-hexyne
(1 mark)
b) State the reagents X and Y
X = H2 and Pd/C
Y = BH3, H2O2, H2O, NaOH
(2 marks)
c) Propose a step wise synthesis of compound B from compound A
(4 marks)
d) Identify compound C and write the mechanism involved.
(4 marks)
e) Predict the major product D
Hydride shift, carbocation rearrangement occured
(1 mark)
Question 2
a). Give the IUPAC name for the following compound
(2 marks)
Answer : 2-hydroxyl-3-hexene
b). Suggest the chemical structures of the products (s) from the following compounds
i)
ii) CH3CH2CH2OH + PBr3

(3 marks)
Answer : i) CH3CH2OH and CH2ICH2CH3 or CH3CH2I and CH3CH2CH2OH
ii) CH3CH2CH2Br
iii)
iv)
v)
Question 3
ANSWERS:
c) i) activator: ethyl
deactivator: Bromo
ii) activator group makes the benzene ring more reactive
Question 4
Suggest the synthesis of 2-methylhexane from molecule A. Give the IUPAC name for
molecule A.
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FINAL TEST

CHM457: FUNDAMENTAL ORGANIC CHEMISTRY

PART A (25 MARKS)

1. Choose the correct product for the following reaction?

2. Predict the product for the following reaction?

A. They have an electrophilic carbon & a good leaving group

5. Predict the product, if 3- bromo-4-methyl-pentane is treated with sodium ethoxide

9. Select the wrong statement about hydroboration of propene.

A. Addition of a B–H bond to the alkene is Markovnikov addition

A. Propyl hydrogen sulphate

11. The reaction between an alcohol and a carboxylic acid yield:

12. Which one of the following compounds is a secondary alcohol?

14. Oxidation of a primary alcohol with PCC in dichloromethane will produce

15. In the conversion: butanol butene, the reagent used is

16. Which of the following is CORRECT about benzene?

A. The molecular formula is C6H5.

17. What is the name of the following compound?

I. 2-bromo-4-ethylaniline II. 1-amino-2-bromo-4-ethylbenzene

Refer to the following reactions to answer question 19 and 20.

19. Identify Compound Y and Reagent I in the above reaction.

20. What is the product(s) form if Compound X is replaced by chlorobenzene?

I. 2-chloro-2-nitrobenzene II. meta-chloronitrobenzene

A. A non-aromatic intermediate is formed

24. Identify the most stable carbocation.

25. Ethyne is also called as

PART B (35 MARKS)

b) State the reagents X and Y

c) Propose a step wise synthesis of compound B from compound A

d) Identify compound C and write the mechanism involved.

e) Predict the major product D

Hydride shift, carbocation rearrangement occured

ii) CH3CH2CH2OH + PBr3

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