SAMPLE QUIZ QUESTIONS - QUIZ S2-2

QUIZ QUESTIONS - HALOALKANES

1. Which of the following compounds ionise to the same carbocation?

Br Br
I III V

Br

Br Br
II IV

A I and II C III and IV E I and V

B II and III D IV and V

2. Which of the following halides gives the highest substitution-to-elimination ratio on being
treated with sodium methoxide?

A C
CH2 CH2 Br CH2 CHBr
CH3
CH3
B D
CHCH 2 CH3 CH2 CCH3
Br Br

3. Which of the following is most suitable for converting CH3 CH2 CH2 Br into
CH3 CH2 CH2 OCH2 CH3 ?

A CH3 CH2 COCl C CH3 CH2 COO- Na+

B CH3 CH2 OH D CH3 CH2 O- Na+

4. The diagram shows the energy profile for the energy

hydrolysis of a haloalkane.
X
Y

Which of the following conclusions can be drawn

from this diagram? progress of reaction

A The reaction is endothermic. C The first reaction is slower than the second.
B X and Y represent intermediates. D An transition state is formed at Z.
Sample Quiz 2.2 page 1
5. Two mechanisms have been proposed for the hydrolysis of 2-bromo-2-methylpropane. One of
these has only one step: (CH3 ) 3 C-Br + OH- → (CH3 ) 3 C-OH + Br-

The other has two steps: (CH3 ) 3 C-Br → (CH3 ) 3 C+ + Br- (slow)
(CH3 ) 3 C+ + OH- → (CH3 ) 3 C-OH (fast)

The reaction is observed to follow first order kinetics. The rate expression is

A Rate = k[(CH3 ) 3 CBr] C Rate = k[(CH3 ) 3 CBr][OH-]

B Rate = k[(CH3 ) 3 C+] D Rate = k[(CH3 ) 3 C+][OH-]

6. What halide will be most resistant to attack by nucleophilic reagents?

A CH3 CH2 -Br C C6 H5 -Br

B (CH3 ) 3 C-Cl D CH3 -CHCl-CH3

Answers 1E 2A 3D 4C 5A 6C

QUIZ QUESTIONS – ALCOHOLS, ETHERS AND PHENOLS

1. In the homologous series of alkanols, increase in chain length from CH3 OH to C2 0H4 1OH is
accompanied by

A increased volatility and increased solubility in water.

B increased volatility and decreased solubility in water.
C decreased volatility and decreased solubility in water.
D decreased volatility and increased solubility in water.

2. Ethers are more volatile than isomeric alcohols because

A ethers contain less oxygen. C ethers have lower molecular masses.

B alcohols have stronger covalent bonding. D alcohols exhibit more hydrogen bonding.

3. CH3 COOH CH3 -CH2 -OH C6 H5 -OH

X Y Z

Which of the following lists the above in order of increasing acid strength?

A X<Y<Z C Y<Z<X
B Z<X<Y D X<Z<Y

4. Which pair of reagents from the list below will react to give the ether CH3 —O—C(CH3 ) 3 as the
major product?
CH3 O- Na+ (CH3 ) 3 CO- K+ CH3 Br (CH3 ) 3 CBr
I II III IV

A I and III C II and III

B I and IV D II and IV

Sample Quiz 2.2 page 2

5. Which of the following compounds would be oxidised to a ketone by acidified dichromate?

CH3 CH3 CH2 CHCH 3

A C
CH3 CHCH 2 OH OH
CH3
OH
B CH3 CCH2 CH3 D
OH
CH2 CH3

6. An organic compound X of molecular formula C4 H1 0O undergoes oxidation to give a compound Y

of molecular formula C4 H8 O2 . X could be

A CH3 CH2 CH2 CH2 OH C (CH3 ) 2 CH-O-CH3

B CH3 CH2 CH(OH)CH3 D (CH3 ) 3 COH

Questions 7 and 8 refer to the following grid

CH3 -CHCl-CH3 1 CH3 -CH(OH)-CH3 2
CH3 -CO-CH3 3 CH3 -CH=CH2 4
CH3 -CH2 -CH2 OH 5 CH3 -CH2 -CH3 6

7. Which compound will react with aqueous sodium hydroxide solution to give an isomer of the
compound in box 5?

A 1 C 3
B 4 D 6

8. The following reaction sequence was performed: reduction, then dehydration; then reaction with
HCl. To which of the following could this sequence be applied?

A 3 2 4 1 C 2 3 4 1
B 4 6 2 1 D 3 2 1 6

9. Pregnenolone, an intermediate in the production of O

contraceptive pills, has the structure

Which one the following statements concerning

pregnenolone is likely to be correct?
HO
A It has an pH<7 in aqueous solution.
B It decolourises bromine solution.
C It readily undergoes electrophilic substitution in the six-membered rings.
D It dissolves in an aqueous solution of sodium hydroxide.

10. A carbonyl compound, X, produced the compound (CH3 ) 2 CHCH2 OH on reduction.

Which of the following was X?

A butanal C butan-2-one
B 2-methylpropanal D 3-methylbutanone

Sample Quiz 2.2 page 3

11. Which of the following is most suitable for converting CH3 CH2 CH2 Br into
CH3 CH2 CH2 OCH2 CH3 ?

A CH3 CH2 COCl C CH3 CH2 COO- Na+

B CH3 CH2 OH D CH3 CH2 O- Na+

12. A carbonyl compound, X, produced the compound (CH3 ) 2 CHCH2 OH on reduction.

Which of the following was X?

A butanal C butan-2-one
B 2-methylpropanal D 3-methylbutanone

Answers 1C 2D 3C 4C 5C 6A 7A 8A 9B
10B 11D 12B

QUIZ QUESTIONS – ALDEHYDES AND KETONES

1. The name of the compound (CH3 ) 2 CHCHO is

A butanal C 1-methylpropanal E 2-methylpropanal

B propanal D 2-methylethanal

2. The best name for the compound (CH3 ) 2 CHCH2 COCH2 CH3 is

A 2-methylhexan-4-one C 5-methylhexan-3-one E isobutylpropanone

B 2-methylhexan-3-one D ethyl isopropyl ketone

3. Which of the following compounds would be oxidised to a ketone by acidified dichromate?

CH3 CH3 CH2 CHCH 3

A C
CH3 CHCH 2 OH OH
CH3
OH
B CH3 CCH2 CH3 D
OH
CH2 CH3

4. Which one of the following reacts with methylmagnesium bromide to form a chiral alcohol?

A acetone C propanal
B ethanal D cyclopentanone

5. The Tollens (silver mirror) test, using a solution of AgNO3 in aqueous ammonia [complex ion
Ag(NH3 ) 2 +], is specific for all:

A alcohols C ketones E alkenes

xB aldehydes D carboxylic acids

Sample Quiz 2.2 page 4

6. O
(1) LiAlH4 (ether)
What is the product of the following reaction: C H ?
(2) H2 O

A CHO C CH2 OH

B COOH D CH2 OH

7. What is the product of the following reaction sequence?

HBr organic (1) Mg, ether organic (1) LiAlH4

(CH3 )3 COH A
product (2) CO product (2) H O+
2 3
+
(3) H3 O

A (CH3 )3 CCH2 OH D (CH3 )3 CCOOH

(CH3 )3 CCCH3 (CH3 )3 CCHCH 3
B E
O OH
C (CH3 )2 CHCHCH 3
OH

8. What reagent and/or reaction conditions would you choose to bring about the following
conversion?
O O
C + HOCH 2 CH2 OH
H
O

A H2 O, H2 SO4 , heat D (1) LiAlH4 (ether); (2) H2 O

B (C5 H5 N)2 CrO3 (CH2 Cl2 ) E H2 / Pt
C H2 O, NaOH, heat

9. Which compound reacts with aqueous acid to give an aldehyde?

O H3C OH
A C
H3C
O O

O OCH3 CH3
B D
OCH3

10. Which of the following compounds does NOT react with aldehydes and ketones?

A LiAlH4 C NH2 OH E CH3 MgBr

B HCOOCH3 D CH3 NH2

Sample Quiz 2.2 page 5

11. Which pair of reagents would you use to prepare the alcohol shown to OH
the right?
C CH2 CH3
CH3

O O
A D
CH3 CH2 MgBr + C6 H5 —CH2 CCH3 C6 H5 MgBr + CH3 CCH2 CH2 CH3
O O
B E
CH3 CH2 MgBr + C6 H5 —CH2 CH CH3 CH2 MgBr + C6 H5 —CCH 3
O
C
CH3 MgI + C6 H5 —CH2 CCH3

12. Which is the major product of the reaction of cyclopentylamine and benzaldehyde followed by
nickel and hydrogen?

A CH2NH C NHCH2

B NH D CH2NHCH2

Answers 1E 2C 3C 4C 5B 6D 7A 8A 9B
10B 11E 12C

Sample Quiz 2.2 page 6