4.
In which of the following molecules carbon atom marked with
Brindhavan Vidhyalaya Public School asterisk (*) is
Unit test – FEB’ 2024
Grade : XII A Sub : CHEMISTRY Date : Marks : 40
I. Choose the correct answers. (20×1=10)
1. The order of reactivity of following alcohols with halogen acids is
Solution: (b) Asymmetric/chiral carbon atom is that in which all of
its four valencies with four different groups or atoms.
5. Which of the following structure is enantiomeric with the molecule
(A) given below:
Solution: (b) The reactivity order of alcohols towards halogen acids is
3° > 2° > 1°, since the stability of carbocations is of the order 3°>2°>1°.
2. Identify the compound Y in the following reaction:
Solution: (a) When a primary aromatic amine, dissolved or
suspended in cold aqueous mineral acid and treated with sodium
nitrite, a diazonium salt is formed. When this freshly prepared
diazonium salt is mixed with cuprous chloride, diazonium group is Solution: (a) Compound (a) is enantiomer of compound (A)
replaced by -Cl. because the configuration of two groups, i.e., CH3 and C2H5 in
Then chlorobenzene is formed which is Y in this reaction. them is reversed at the chiral carbon.
6. Which of the following is an example of vie-dihalide?
(a) Dichloromethane (b) 1, 2-dichloroethane
(c) Ethylidene chloride (d) Allyl chloride
3. Which reagent will you use for the following reaction?
Solution: (b) 1, 2-Dichloroethane is a vic-dihalide since two Cl
atoms are present on vicinal carbon atoms (adjacent).
Solution: (a) The given reaction is a free radical substitution
reaction. It occurs in presence of ultraviolet light or at high
temperature or peroxides which are free radical generators. Free
radical substitution cannot take place in dark. 7. The position of -Br in the compound CH3CH – CHC(Br)(CH3)2,
can be classified as .
(a) allyl (b) aryl (c) vinyl (d) secondary
Solution: (a) It is allylic compound in which Br is attached next to which has lesser number of hydrogen.
double bonded carbon.
11. A primary alkyl halide would prefer to undergo .
8. Chlorobenzene is formed by reaction of chlorine with benzene in (a) SN1 reaction (b) SN2 reaction
the presence of AlCl3. Which of the following species attacks the (c) a-Elimination (d) Racemisation
benzene ring in this reaction? Solution: (b) SN2 reaction proceeds via formation of transition
(a) CP (b) Cl+ (c) AlCl3 (d) [AlCl4]– state which is formed easily in primary alkyl halide due to less
Solution: steric hindrance.
12.
9. Ethylidene chloride is a/an .
(a) vic-dihalide (b) gem-dihalide (c) allylic halide (d) vinylic halide
Solution: (b) Ethylidene chloride is a gem-dihalide, CH3 – Solution: (c) The correct IUPAC name of the given compound is
CHCl2 in which both halogen atoms are attached to the same 13. Molecules whose mirror image is non superimposable over them
are known as chiral. Which of the following molecule is chiral in
carbon atom.
10. What is A in the following reaction? nature?
(a) 2-Bromobutane (b) 1-Bromobutane
(c) 2-Bromopropane (d) 2-Bromopropan-2-ol
Solution:
Solution: (c) In this reaction, addition of HCl takes place on doubly
bonded carbons in accordance with Markownikofif’s rule i.e.,
addition of negative addendum will take place on that carbon
14. Which of the carbon atoms present in the molecule given below (b) 1-Iodobutane < 1-Bromobutane < 1-Chlorobutane < Butane
are asymmetric? (c) Butane < 1-Iodobutane < 1-Bromobutane < 1-Chlorobutane
(d) Butane < 1-Chlorobutane < 1-Iodobutane < 1-Bromobutane
Solution: (a) The higher the surface area, the higher will be the
intermolecular forces of attraction and thus boiling point too.
Boiling point increases with increase in molecular mass of
halogen atom for the similar type of alkyl halide. Butane has no
halogen atom and rest of all three compounds are halo derivatives
of butane.
Atomic mass of iodine is highest so the boiling point of 1-
iodobutane is maximum among all the given compounds.
Solution: (b) Carbon has four valencies. If a carbon atom satisfies
all of its four valencies with four different groups then it is termed
17. p-dichlorobenzene has higher melting point than its o- and m-
asymmetric/chiral carbon. In the given compound, b and c carbon
are bonded to four different groups, so these are asymmetric. isomers. Why?
(a) m- dichlorobenzene is more polar than o-isomer
(b) p-isomer has a symmetrical crystalline structure
15. Which of the following compounds will give racemic mixture on
(c) boiling point of o- isomer is more than p-isomers
nucleophilic substitution by OH ion?
(d) All of these are correct
Answer: (b) p-isomer has a symmetrical crystalline
structure
18. How many structural isomers are possible for a
compound with molecular formula C3H7Cl ?
(a) 2
Solution: (b) 5
(c) 7
(d) 9 Ans. (a)
19. The compound which contains all the four 1°, 2°, 3°
and 4° carbon atoms is
(a) 2, 3-dimethyl pentane
16. Which is the correct increasing order of boiling points of the (b) 3-chloro-2, 3-dimethylpentane
following compounds?
1-Iodobutane, 1-Bromobutane, 1-Chlorobutane, Butane (c) 2, 3, 4-trimethylpentane
(a) Butane < 1-Chlorobutane < 1-Bromobutane < 1 -Iodobutane (d) 3, 3-dimethylpentane Ans. (b)
20. C – X bond is strongest in higher boiling point.
(a) CH3Cl (b) Racemic mixture contains equal amount of dextro and laevo
rotatory compounds. Half of molecules rotate plane polarised light
(b) CH3Br towards left, remaining half towards right such that net optical
(c) CH3F rotation is zero. Therefore, Racemic mixture is optically inactive.
(d) CH3I
Ans. (c) Because of the small size of F, the C–F bond is
strongest in CH3F.
II. Answer all the following questions. (5×2=10)
21. Hydrolysis of optically active 2- bromobutane forms optically
inactive butan – 2 – ol. 23.
Ans.
The compound undergoes hydrolysis by SN1 mechanism via the
formation of carbocation which is planar.
24. Draw the structure of major monohalo product in each of the
following reactions:
The attack of nucleophile can result in product which is a mixture of
compounds both with same configuration and inverted
configuration.
Answer:
25. Write about Finkelstein and swarts reaction.
Therefore it results in the formation of racemic mixture which is Alkyl iodides are often prepared by the reaction of alkyl chlorides/
bromides with NaI in dry acetone. This reaction is known as Finkelstein
optically inactive.
reaction. NaCl or NaBr thus formed is precipitated in dry acetone. It
22. Give reasons:
facilitates the forward reaction according to Le Chatelier’s Principle.
(a) n-Butyl bromide has higher boiling point than f-butyl
bromide.
The synthesis of alkyl fluorides is best accomplished by heating an alkyl
(b) Racemic mixture is optically inactive. chloride/bromide in the presence of a metallic fluoride such as
(a) It is because n-butyl bromide has more surface area than i-butyl AgF, Hg2 F2 , CoF2 or SbF3 . The reaction is termed as Swarts reaction
bromide, therefore, more van der Waals’ forces of attraction, hence
Ans. (i)
III. Answer all the following reactions 2-Chloro-3-methyl pentane
26. The substitution reaction of alkyl halide mainly occurs by S N1 or (ii)
SN2 mechanism. Whatever mechanism alkyl halides follow for the
substitution reaction to occur, the polarity of the carbon halogen bond
is responsible for these substitution reactions. The rate of SN1 reactions
are governed by the stability of carbocation whereas for SN2 reactions
steric factor is the deciding factor. If the starting material is a chiral
compound, we may end up with an inverted product or racemic
mixture depending upon the type of mechanism followed by alkyl
1-Chloro-4-ethylcyclohexane
halide. Cleavage of ethers with HI is also governed by steric factor and
(iii)
stability of carbocation, which indicates that in organic chemistry,
these two major factors help us in deciding the kind of product formed.
a) Predict the stereochemistry of the product formed if an 4- tert-Butyl-3-iodoheptane
optically active alkyl halide undergoes substitution reaction by (iv)
SN1 mechanism.
b) Name the instrument used for measuring the angle by which the
plane polarized light is rotated. 1, 4-Dibromobut-2-ene
c) Predict the major product formed when 2-Bromopentane reacts with (v)
alcoholic KOH.
d) Predict the stereochemistry of the product formed if an optically
active alkyl halide undergoes substitution reaction by SN1
mechanism
e) Give one use of CHI3.
27. Write structures of the following compounds: 1-Bromo-4-sec-butyl-2-methylbenzene
(i) 2-Chloro-3-methylpentane
(ii) 1-Chloro-4-ethylcyclohexane
(iii) 4-tert. Butyl-3-iodoheptane
(iv) 1,4-Dibromobut-2-ene
(v) 1-Bromo-4-sec. butyl-2-methylbenzene
