University of Bahri

Second year Second semester main Exam 2015

Organic reaction type
Date: /
/2015
Time allowed: 3 Hrs
Q1: Draw circle around the best answer:
1. The inductive effect can be best described as:
a) The ability of atom or group to cause bond polarization
b) The transfer of lone pair of electrons from more
electronegative atom to lesser electronegative atom in a
molecule.
c) The conjugation of -bonding orbital with the adjacent orbital
d) All of the above.
2. Which of the following statement is incorrect about the inductive
effect?
a) It involves delocalization of -electrons
b) It is a permanent effect
c) It involves displacement of -electrons
d) It decreases with increases of distance
3. Which of the following shows positive (+I) inductive effect?
a) NH2
b) OCH3
c) C6H5
d) CH2CH3
4. Which of the following compounds would exhibit aromatic properties?

5. Which of the following cation is most stable?

a) (CH3)3C
b) (CH3)2CH
c) (CH3)CH2
d) CH3

6. Which of the following statement is incorrect about the

Conjugation?
a) Conjugation is the overlap of one p-orbital with another
across an intervening sigma bond
b) Conjugation general may lower the overall energy of the
molecule and increase stability.
c) Lone pairs, radicals or carbenium ions may be part of the
conjugate system.
d) Conjugation
allows
a
delocalization
of sigma
electrons across all the adjacent aligned p-orbitals.
7. Which of these have only -R (negative resonance effect?)
a. -NO2,-OH,-CHO
b. -CHO,-COOH,-OCH2
c. -NO2,-CN,-SO3H
d. -NHCOCH3,-COCH3,-SO3H3.
8. The order of acid strength
a) CH3COOH
b) CH2FCOOH

c) CHF2COOH

d) CF3COOH

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

b) (c) > (d) > (b) > (a)
c) (d) > (c) > (a) > (b)
d) (d) > (c) > (b) > (a)
9. Which of the following statement is incorrect about the
hyperconjugation?
a) The stability of alkenes increases with hyperconjugation.
b) Stability of carbonations (carbonium ions) increases with
hyperconjugation
c) Stability of free radicals decreases with hyperconjugation
d) Reactivity & orientation of electrophilic substitution on
benzene ring increase due to hyperconjugation
10.
In -halo alkenes, the delocalization of electrons occurs
towards halogen group through:
a) Conjugation
b) Hyperconjugation
c) Reverse hyperconjugation
d) None of them

Q2: True or false

1. The inductive effect can be best described as the ability of atom

or group to cause bond polarization (
)
2. The inductive effect decreases with increases of distance (
)
3. NH2 shows positive (+I) inductive effect (
)
4. CH3 cation is more stable than (CH3)3C cation (
)
5. Conjugation allows a delocalization of sigma electrons across all
the adjacent aligned p-orbitals. (
)
6. NHCOCH3,-COCH3,-SO3H3 have -R negative resonance effect (
)
7. CH2FCOOH is stronger acid than CH3COOH (
)
8. The stability of alkenes, carbonations, and free radicals increases
with hyperconjugation. (
)
9. Nitrobenzene show both +R effect and -I effect (
)
10.
In -halo alkenes, the delocalization of electrons occurs
towards halogen group through Reverse hyperconjugation (
)
11.
NH2 group is ortho para director in electrophilic aromatic
substitution (
)
12.
Benzene undergoes substitution reaction rather than
addition reaction (
)
13.
SO3H group is meta director in electrophilic aromatic
substitution (
)
14.
One of the characteristic of an aromatic compound that the
number of delocalized electrons is even, but not a multiple of
4. (
)
15.
Polycyclic aromatic hydrocarbons are molecules containing
two or more simple aromatic rings fused together by sharing one
neighboring carbon atoms (
)
Q3:
a) Why NH2 group is ortho, para director in electrophilic aromatic
substitution
b) Write down one of the reaction of benzene
c) How you can prepare aromatic aldehyde and ketone (give one
method of each)
d) How you can Prepare O-chlorotoluene from O-toludine.
e) How you can prepare O and P-nitro aniline from aniline
f) How you can prepare p-methyl benzoic acid (p-toluic acid) from
toluene

Q4: Complete the following reaction:

N=N

1)

LiALH4
Metal chloride

NH2
Br2(aq)

2)

CH3
HNO3
H2SO4

3)

Fe

NaNO2

HCl

HCl

CuCN

H2O
H+

Cl
4)

+ NaOH

Heat

CH3
NO2
5)

Cl2

Fe / HCl

Fe

NaNO2
HCl

CuCl

H2 O
Conc H2SO4

Cl2at B.P

NO2
6)

Br2(aq)

Sn
HCl

NaNO2
HCl

Q5:
In Cannizaro reaction:
2C6H5CHO + NaOH

C6H5CH2OH + C6H5COONa.

Write down the mechanism of this reaction

H2O
H+