Organic Chemistry MCQ

(12)1, 19
Covalent bonds are formed by orbital overlap. The shape of unsaturated hydrocarbon
molecules can be explained in terms of hybridisation of orbitals.
Which bond is not present in HCCCH
2
CH=CH
2
?
A. A bond formed by 2p-2p overlap
B. A bond formed by 1s-2sp overlap
C. A bond formed by 2sp-2sp
2
overlap
D. A bond formed by 2sp
2
-2sp
3
overlap
(12)1, 20
When heated with chlorine, the hydrocarbon 2,2-dimethylbutane undergoes free radical
substitution. In a propagation step, the free radical X is formed by the loss of one hydrogen
atom.
H
3
CH
2
C
CH
3
CH
3
C H
3
+
Cl X
+
Cl H

How many different forms of X are theoretically possible?
A. 1
B. 2
C. 3
D. 4
(12)1, 21
PGE
2
and PGF
2
are two prostaglandins, both with pharmacological activity.
O
O H
CO
2
H
O H
CH
3
O H
O H
CO
2
H
O H
CH
3


A. H
2
/Ni
B. H
2
/Pt
C. H
2
O/H
+

D. NaBH
4

PGE
2

PGF
2

(12)1, 22
The diagram shows the structure of the naturally-occurring molecule cholesterol.
O H
CH
3
H
H
H
CH
3
H
C H
3
CH
3
C H
3

Cholesterol reacts with cold, dilute acidified KMnO
4
.
Four students made claims about this reaction.
W The cyclohexene ring becomes saturated.
X The cyclohexene ring is broken open.
Y The number of chiral centres increases by 1.
Z The number of chiral centres increases by 2.
Which students claims are correct?
A. W and Y
B. W and Z
C. X and Y
D. X and Z
(12)1, 23
The diagram represents the transition state of an S
N
2 reaction in which N is an anionic
nucleophile and L the leaving group, but without any indication of the location of positive or
negative charges.
C
C H
3
CH
3
CH
3
N L

Which is a possible combination of charges?
Charge on N Charge on L
A - +
B - -
C + +
D + -

(12)1, 24
Chlorofluorocarbons (CFCs) have been widely used in aerosol sprays, refrigerators and in
making foamed plastics, but are now known to destroy ozone in the upper atmosphere.
What will not destroy ozone, and therefore can be used as a replacement for CFCs?
A. CHBr
3

B. CCl
3
CBr
3

C. CHClFCClF
2

D. CH
3
CH
2
CH
2
CH
3

(12)1, 25
Rosmarinic acid occurs in culinary herbs such as rosemary, sage and thyme.
O H
OH
O
O
OH O
OH
OH

How many moles of NaOH(aq) will react with one mole of rosmarinic acid when the acid is
heated under reflux with an excess of NaOH(aq)?
A. 4
B. 5
C. 6
D. 7
(12)1, 26
Cattle suffering from stress produce 6-methylhept-5-en-2-one, which repels mosquitos.
(CH
3
)
2
C=CHCH
2
CH
2
COCH
3

Which property will 6-methylhept-5-en-2-one possess?
A. Addition of Br
2
(aq) produces a chiral compound.
B. Prolonged heating with acidified concentrated KMnO
4
produces HO
2
CCH
2
CO
2
H.
C. Reduction by a methanolic solution of NaBH
4
produces a compound C
8
H
18
O.
D. Warming with alkaline aqueous I
2
produces CH
3
CO
2
H.

(12)1, 27
What stabilises the -helix of proteins?
A. Disulfide bridges and hydrogen bonding
B. Disulfide bridges only
C. Hydrogen bonding only
D. Van der Waals forces only
(12)1, 28
After the reduction of nitrobenzene to phenylamine using tin and concentrated hydrochloric
acid, an excess of sodium hydroxide is added.
What is the purpose of the sodium hydroxide?
A. To dry the product
B. To liberate the phenylamine
C. To lower the boiling point for subsequent distillation
D. To precipitate tin(II) hydroxide
(12)1, 29
Why are amides, RCONH
2
, less basic than amines, RNH
2
?
A. Amides form zwitterion in which the nitrogen atom carries a positive charge.
B. Amides have a resonance structure involving the movement of a pair of electrons
from nitrogen atom to the oxygen atom.
C. Electrons on the nitrogen atom move on to the C-N bond giving it some double
character so that it is more difficult to break.
D. The amide carbonyl group withdraws electrons from the NH
2
group to make the
hydrogen atoms acidic.

(12)1, 30
When 2-methylphenylamine reacts with an excess of Br
2
(aq), one of the intermediates is
cation Z.
NH
2
CH
3
Br
NH
2
CH
3
H
Br
+

What is the final product of this reaction?

NH
2
CH
3
Br
Br
NH
2
CH
3
Br
NH
2
Br
Br
Br
NHBr
CH
3
Br
Br

(12)1, 37
During the preparation of many organic compounds by-products are formed. This usually
occurs because the reagents can react in more than one way depending on the conditions used
or because the products formed may react with the reactants.
Propan-1-ol is produced by the reaction between 1-bromopropane and aqueous sodium
hydroxide.

What could be a by-product of this reaction?
1. CH
3
CH=CH
2

2. CH
3
CH
2
CH
2
ONa
3. CH
3
CH(OH)CH
3


A B C D
(12)1, 38
The mould Phytophthora damages many plants, destroying agricultural crops such as
potatoes. A hormone-like compound called alpha1 regulates the reproduction of all species of
Phytophthora. The structure of alpha1 is now known, giving scientists a key to the possible
future eradication of the mould.
O H
CH
3
O
CH
3
OH
CH
3
CH
3
OH

Which will react with alpha1?
1. Cl
2
(g)/light
2. SOCl
2

3. H
2
/Pt
(12)1, 39
Bromoethene, CH
2
=CHBr, is unreactive to nucleophiles whereas 3-bromopropene,
CH
2
=CHCH
2
Br, is very reactive by comparison.
What could be a reason for the lack of reactivity of CH
2
=CHBr?
1. The electrons of the bromine atom delocalise into the bond.
2. The electrons of the bond repel the attacking nucleophile.
3. The presence of the bond prevents free rotation of the C-Br bond thus decreasing
the reactivity.

(12)1, 40
In an industrial process, heptane vapour is passed over a heated catalyst to make
methylbenzene.
CH
3
CH
2
CH
2
CH
2
CH
2
CH
2
CH
3
CH
3
+
H
2
4

Under similar conditions, which of the C
8
H
18
isomers could give 1,4-dimethylbenzene?
CH
3
C H
3


CHCH
2
CH
2
CH
2
CH
3
H
3
CH
2
C
C H
3
C H
3
CH
3
CH
3
CH
3
CHCH
2
CH
2
CH
2
CH
2
CH
3
C H
3
C H
3

(11)1, 19
Which statement about the molecule but-2-yn-1-ol is not correct?
C H
3
OH
1
2 3 4

A. The centre carbon atoms (2 and 3) are sp hybridised.
B. The molecule decolourises warm acidified KMnO
4
.
C. The terminal carbon atoms (1 and 4) are sp
2
hybridised.
D. The terminal carbon atoms (1 and 4) have tetrahedral geometry.

1


2


3
(11)1, 20
The complete combustion of alkanes to produce carbon dioxide and water is an important
exothermic reaction.
Which line on the graph shows the relationship between the number of carbon atoms in the
alkane and the number of moles of oxygen gas needed for complete combustion of the
alkanes?








(11)1, 21
Chloroethene, CH
2
=CHCl, is unreactive to nucleophiles whereas 3-chloropropene,
CH
2
=CHCH
2
Cl, is very reactive by comparison.
What explains the lack of reactivity of CH
2
=CHCl?
A. Substituted alkenes undergo only electrophilic addition.
B. The C=C double bond and the Cl atom are both electron withdrawing which stabilises
CH
2
=CHCl.
C. The electrons on the Cl atom delocalise into the bond.
D. The presence of the bond prevents free rotation of the C-Cl bond thus decreasing the
reactivity.

1
Number of moles
of oxygen gas
Number of carbon
atoms in alkane

A
B
C
D
(11)1, 22
Which species could be an intermediate in an S
N
1 substitution?

C H
3
Cl
O
-
OH
CH
2
+
H
CN
+
C
C H
3 CH
3
CH
3
O H
-
Br
-

(11)1, 23
The diagram shows a reaction.
CH
2
CO
2
steam, H
+
Z

What could be the final products Z?

CH
2
CO
2
H
+
O H
CH
2
CO
2
H
+
O H OH
CH
2
CO
2
H
+
O H OH
OH
CH
2
OH
+
HO
2
C

A


B


C


D
A

B


C

D
(11)1, 24
A comparison is made of the rate of hydrolysis of four halogenocompounds by warm
NaOH(aq).
CH
3
CH
2
COCl C
6
H
5
Cl (CH
3
)
3
CBr (CH
3
)
3
Cl
W X Y Z
How will these rates compare?
Fastest Slowest
A W Y Z X
B W Z Y X
C X Z Y W
D Z Y X W

(11)1, 25
The reaction conditions for four different transformations are given below.
Which transformation has a set of conditions that is not correct?

CH
4
(g) + Cl
2
(g) CH
3
Cl + HCl
UV
light
C
6
H
6
(l) + HNO
3
(conc.) C
6
H
5
NO
2
+ H
2
O
conc. H
2
SO
4
55 C
CH
3
(l) + Cl
2
(aq) + HCl
AlCl
3
(s)
heat
CH
3
Cl
OH
(aq) + HNO
3
(dilute) + H
2
O
OH
NO
2


A

B


C


D
(11)1, 26
Compound P, C
4
H
10
O
2
, is an alcohol containing two OH groups per molecule. It can be
oxidised in stages to compound Q, C
4
H
8
O
2
, and then to compound R, C
4
H
6
O
2
, which is a
diketone.
Which pair of statements about the properties of P, Q and R is correct?
Has 2 chiral centres Reacts with alkaline
aqueous iodine to give
tri-iodomethane
A P only P, Q and R
B P only Q and R only
C P and Q only Q and R only
D P, Q and R P, Q and R

(11)1, 27
In the following two-step synthesis, Y a solid which is insoluble in water, is one of the
components in the final reaction mixture.
CO
2
H
CO
2
H
PCl
5
, warm
X
NH
3
then heat
Y

What is Y?

CO
NH
CO
CH
2
OH
CONH
2
CH
2
NH
3
+
CO
2
-
CH
2
NH
2
CO
2
-
NH
4
+


A B C D
(11)1, 28
Compounds X, Y and Z all react with sodium to release hydrogen but only one of them reacts
with 2,4-dinitrophenylhydrazine reagent.
Which combination could be X, Y and Z?
X Y Z
A
CH
2
OH
CH
2
OH

CHO
CHO

CO
2
H
CO
2
H

B
CH
2
OH
CH
2
OH

CH
2
OH
CHO

CHO
CO
2
H

C
CH
2
OH
CHO

CH
2
OH
CO
2
H

CHO
CO
2
H

D
CH
2
OH
CO
2
H

CHO
CO
2
H

CO
2
H
CO
2
H


(11)1, 29
The compounds responsible for the umami flavour of soy sauce are salts of glutamic acid.
HO
2
CCH
2
CH
2
CH(NH
2
)CO
2
H
Glutamic acid has pK
a
values of 2.1, 4.1 and 9.5.
What is the structure of the major species in a solution of glutamic acid at pH 7?

O
2
C
-
CO
2
-
N H
2
O
2
C
-
CO
2
-
N H
3
+
HO
2
C
CO
2
-
N H
3
+
HO
2
C
CO
2
H
N H
3
+



A B


C D
(11)1, 30
Oseltamivir is an anti-viral drug.
OR
CH
3
COHN
N H
2

What is the product when oseltamivir is heated with HCl(aq)?

OR
CH
3
COHN
N H
3
+
CO
2
CH
2
CH
3
OR
N H
3
+
N H
3
+
CO
2
H
OR
N H
3
+
N H
3
+
CO
2
CH
2
CH
3
OR
CH
3
COHN
N H
3
+
CO
2
H

(11)1, 33
The three compounds X, Y and Z have the following structures.
O H
N
N
OH
N
N
CO
2
CH
3
CH=CH
2
N
O


Which statements about X, Y and Z are correct?
1. X and Z have the same empirical formula.
2. X and Y are isomers.
3. The M
r
of Y is exactly twice that of Z.

[-OR is inert]
A B



C D
X Y Z
(11)1, 37
Swine flu has caused great concern internationally. One widely used treatment is the anti-
viral drug Tamiflu.
OCH
2
CH
3
O
(H
3
CH
2
C)
2
HCO
NH
NH
2
CH
3
O

Which statements about the Tamiflu molecule are correct?
1. It contains an amide group.
2. It contains two ester groups.
3. It contains four chiral centres.
(11)1, 38
A catalytic converter is part of the exhaust system of many modern cars.
Which reactions occur in a catalytic converter?
1.

2.

3.

(11)1, 39
Baeyers reagent is used to detect carbon-carbon double bonds: a dilute alkaline solution of
KMnO
4
loses its pink colour in the presence of such a bond.
In which tests does a positive result involve a reduction in the oxidation number of the metal
present in reagent?
1. Baeyers test
2. Fehlings test
3. Tollens test

(11)1, 40
Spider silk is a protein composed mainly of the three amino acids alanine, glycine and serine.
NH
2
CH(CH
3
)CO
2
H NH
2
CH
2
CO
2
H NH
2
CH(CH
2
OH)CO
2
H
Alanine glycine serine
Which type of bonding can occur in the tertiary structure of spider silk?
1. Van der Waals forces
2. Hydrogen bonding
3. Ionic bonding