MONTH- OCTOBER

SUBJECT-CHEMISTRY
Unit-Hydrocarbons
1. Out of n-pentane, isopentane and neopentane, which has lower boiling point and
why?

2.(a) Ozonolysis of the alkene 'X' followed by

and zinc gave a mixture of acetone and decomposition of the ozonide with water
alkene 'X. Name it by IUPACsystem. formaldehyde. WVrite down the structure of
(b)The following alkene undergoes reductive ozonolysis. Write the structure and
names of compounds formed after the process lUPAC
CH3 -C( CH3 )= CH- CH3
3. Which alkene on oxidation with hot alkaline KMnO , gives acetic acid and carbon
dioxide?

4. DrawW and show the orbital

interaction between sigma bond of a constituent group and
neighbouring pi orbital.
5. Why the unsaturated hydrocarbons and aromatic compounds burn with more
flame than the saturated sooty
hydrocarbons?
6. Write the major product obtained by dehydration of butan -2- ol. Explain your
answer.

7. Account for the order of acidity -

Acetylene > benzene > hexane

8.Butanone is fomed when an alkyne is passed through a dilute

330K in the presence of HgSO4. Write the possible solution of H2 SO4 at
structure of the alkyne
9. What happens when -
a) Propyne is heated with hydrogen in the
presence of nickel at 473 K
b) Isopropyl magnesium bromide is treated with water.
c) Acetylene is treated with water in the
presence of dilute H2 SO4 and HgSO,

10. Give one word

(a)Name of a Lewis acid other than anhydrous
during ethylation of benzene.
aluminium chloride which can be used
(b)Negative part of the addendum goes to that carbon which has less number of
hydrogens.
(c)Decomposition of acompound by application of heat.
 T1. Name the products which may be obtained when a mixture of methyl bromide and
ethyl bromide is treated with sodium metal in ether .

12. Draw the structures of three cvcloalkane isomers with molecular formula Gs Hi0
each with a different size ring Write their names also

13. Which of the following are meta directors -

-NO2, -SO, H, -CI, -OH, -NH2, -CHO

14. Which of the following molecules are aromatic? Give reason.

Cyclopropane, cyclopropenyl cation , cyclopropenyl anion , cyclopentadiene
pyridine, pyrrole, furan , naphthalene, anthracene
15. Give steps for the preparation of -
a) Acetone from propene
b) Benzoic acid from benzene
c) Ethene from ethanol
d) Glyoxal from ethyne
16. The hydrocarbon 'A' adds one mole of hydrogen in the presence of a platinum
catalyst to form n - hexane. When 'A' is oxidized vigorously with KMnO4 ,a single
carboxylic acid containing three carbon atoms is isolated. Give the structure of 'A' and
explain.

17. An alkane 'A' with molecular formula 72 gives four monochlorinated products on
reaction with chlorine in the presence of light. Draw their structures.

18. Write the structure of alkene (major product ) obtained when 2 - Chlorobutane is
treated with C, Hs ONa*

19. Account for the following -

a) Nitrobenzene does not undergo friedal craft alkylation
b) NH, is more activating group than -OH although oxygen in -OH has lone pairs of
electrons present on it.
c) Nitric acid alone does not reacts with benzene but a reaction occurs if
concentrated sulphuric acid is present
d) Cl group is ortho -para directing but deactivating group.
e) Phenol is more acidic than methanol.

20.Count total number of sigma and pi bonds in the enolic form of acetone.

21. Arange the following compounds in order of increasing rate of reaction with HNO,
and H, SO,
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 Support your answer.

A B C D

Nitrobenzene Phenol Toulene Chlorobenzene

b Benzoic acid Nitro benzene Benzene Toulene

22. Arrange the given compounds in increasing order of Ka. Give reason also.
Propyne, Hex-2-yne , ethyne, ethane, ethene

23. How will you distinguish between CH,CH,C =CH and CH3C = CCH
24. Drawthecis and trans isomers of hex-2-ene. Which will have higher boiling point
and why?

25. Identify A, B,C,D in the following reaction

A 'B'KOt,
NN9 'C Hg H,se+ D

C ’ CH3-C CAg*
White ppt

26.Why is peroxide effect seen only in case of HBr and not in case of HCl or HI?

27.An unknown alkene 'A' on reductive ozonolysis gives two isomeric carbonyl
compound 'B' and 'C' of molecular fomula C3 Hs O. Write the structures of A'Band
'C

28. Find the structure of hydrocarbon that produces one mole each of ethanedial and
butanedial on ozonolysis.

29.0ne mole of hydrocarbon 'A' reacts with one mole of bromine giving a
dibromocompound,CsHo Br2 "A' on reaction with cold dilute alkaline KMnO, forms Cs
H2 O2.On ozonolysis Agives equimolar quantities of propanone and ethanol. Find out
the structural formula of Aand write the reactions involved

30.During nitration, in the process of generation of nitronium ion, sulphuric acid serves
as an acid and nitric acid as a base. Support this statement by writing steps showing
generation of nitronium ion with curved arrows.
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31.Label all 3 and 4 carbon atoms in bond line notation of 3,4 - Dimethyl- 4
ethylnonan-5 -one

32. Explain how does the- OH group attached to a carbon of benzene ring activate it
towards electrophilic substitution ?

33. Write equations of the following reactions

(a) Friedal - Crafts reaction - alkylation of anisole
(b) Friedal - Crafts reaction - acetylation of anisole
(c)Nitration of anisole.
34. Propyne is weaker acid than ethyne. Why ?
35. lodination of alkane is done in the presence of an oxidizing agent. Why ?
36. Complete the following reaction
Alc KOH HBr ( Peroxide )
CH3 CHz CH2 Ci

37. How many dichlorosubstitution products are possible for iso - butane ? Give their
structures and IUPAC names

38. Why chlorination of ethane to ethyl chloride is more practicable than the chlorination
of n- pentane to 1- chloropentane?
39. An alkyl halide Cs H11 Br "A" reacts with ethanolic KOH to give an alkene "B"
which reacts with bromine in carbon tetrachloride to give "C" ,which on
dehydrobromination gives an alkyne "D". On treatment with sodium metal in liguid
ammonia one mole of "D" gives one mole of sodium salt of "D" and half a mole of
hydrogen gas. Complete hydrogenation of "D° gives a straight chain alkane . ldentify A
B,C,D. Write reactions

40. Write the mechanism involved in the generation of -

(a) phenyl free radical from benzoyl peroxide
(b)nitronium ion during nitration of benzene

41. Cs H1 Br on reaction with Na/ether gives 2,2,5,5- tetramethylhexane . Assign

structure to the compound.

Can you do it

42. Compare acidity of phenol and ethanol.

43. Arrange the following compounds in increasing order of their acid strength :
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 (a)CH, CH, CH (Br)COOH. CH, CH(B)CH, COOH. (CH3 >
COOH CHCOOH, CH3 Or?
(O)0enZOIC acid,4- nitrobenzoic acid. 3.4 - Dinitrobenzoic acid
4- Methoxybenzoic acid
Give reason also.

44. Aniline doesnot undergo Friedal Crafts reaction. Why ?

4O.Keaction of ethyl chloride with aqueous KOH gives ethanol while with alcoholic KOH
gives ethene. Explain.

46.Higher alkyl substituted alkene is formed in greater proportion than the lower alkyl
substituted alkene. Justify
47.Reactivity of neopentyl benzene is slow while isopropyl benzene is fast towards
monochlorination in the presence of sunlight. Why ?

48.The products formed on dehydration of isomers of C4 HÍ OH difer in their stability

identify the most stable and least stable product.

49.A compound Ce H10, reacts with one mole of hydrogen. The resultant compound
on monochlorination forms one compound but on dichlorination forms four different
compounds. The compound Å'on ozonolysis forms hexane - 1,6 -dial but foms
hexane -1,6- dioic acid with acidic potassium permanganate. ldentify A, write it's
IUPAC name.

50.But-2- yne on controlled hydrogenation under different conditions give isomers

( molecular formula C4 Ha ),these isomers have different melting point. ldentify them
and give reason for the difference in their melting points .Write the reactions
51.Write IUPAC name of products formed
(a)Oxidation of ethene with baeyer's reagent
(b)Acetylene is treated with red hot iron

52.Explain why alkenes undergo electrophilic addition reactions ?

53.Write possible structure of -

(a)alkyl halide which on reduction gives ethane
(b)Alcohol which on dehydration gives but - 2 -ene

54.Arrange the givern compounds in order of Ka value

Propanoic acid , acetic acid , nitroacetic acid, chloroacetic acid
Give reason also

55.Write possible structure and IUPAC name of the alkyl chloride which on
dehydrohalogenation forms only a single alkene C4 Ha . The alkene on reductive

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OZonolysis forms 2 moles of acetaldehvde and with acidic potassium permanganate
forms 2 moles of acetic acid only

56.Write lIUPAC name and structure of alkene which on reductive ozonolysis forms two
moles of acetophenone

57.Arrange possible alkenes which on hydrogenation form secondary butyl benzene in

order of stability

MCQ-(Q 58 -Q 60 )
58.Which of the following is most reactive ?
(a)Cyclopropane (b) Cyclobutane (c) Cyclopentane (d) Cyclohexane

59.The order of reactivity of hydrogen halides with propene is -

(a)HC| > HBr > HI (b) HBr > HI > HCI
(c )H| > HBr > HCI (d) HC| > HI > HBr

60.The molecule having dipole moment is -

(a)2,2 - Dimethylpropane (b)trans - Pent-2 -ene
(c )But-2- ene (d) 2,2,3,3- Tetramethylbutane

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