DPP 1 : HYDROCARBONS

PREPARATION OF ALKANES

SUBJECTIVE ASSIGNMENT

Q1. Name the chain isomer of C5H12 which has a tertiary hydrogen atom? Amongst all isomers, which one has
the maximum boiling point?
Q2. Explain why dry ether is used as a solvent in Wurtz reaction.
Q3. Explain why the branching of alkane chain lowers its boiling point?
dryether  / catalyst
Q4. Complete the following reaction (i) CH3-Cl +Na   ? (ii) C3H8 + 3H2O   

Q5. Name the compound that will be required to obtain butane using Kolbe’s electrolysis?
Q6. Draw the conformations of ethane using sawhorse formula.
Q7. What effect does branching have on the boiling point of an alkane and why?
Q8. Give a brief account of following: (i) n- Pentane has greater boiling point than iso-pentane
(ii) CH4 cannot be synthesized by Wurtz reaction

Q9. Arrange the following in increasing order of boiling point: Pentane, 2-methylbutane,
2,2 Di-methylpropane
Q10. Draw the Newman projections of eclipsed and staggered conformers of ethane. Which of the two is stable
and why?
Q11. Explain the following reactions: (i) Wurtz reaction (ii) Decarboxylation (iii) Kolbe’s electrolysis
Q12. How can you convert : (i) Ehtyne to Ethane (ii) n-Hexane to Benzene (iii) Methane to chloromethane
(iv) methane to methanal (v) n-Butane to isobutane

Q13. Write the combustion reaction for : (i) Butane (ii) Hexane
Q14. Write the structures of different chain isomers of alkanes corresponding to the molecular formula C 6H14.
Q15. Write the IUPAC names of the following: (i) (CH3)3CCH2C(CH3)3 (ii) (CH3)2C(C2H5)2
Q16. Write the structural formula of the following: (i) 3,4,45-Tertamethylheptane (ii) 2,5-
Dimethylhexane(iii) Tetra-tert-butylmethane
Q17. Sodium salt of which acid is needed for the preparation of propane ? Write the chemical equation for the
reaction.
Q18. How do you account for the formation of ethane during chlorination of ethane?
OBJECTIVE ASSIGNMENT

Q1. The products of the following reactions is(are) C2H5Br + 2 Na + CH3Br dry ether
  ?
(a) ethane (b) propane (c) butane (d) ethane, propane and butane
Q2. An alkyl bromide (X) reacts with sodium in ether to form 4, 5-diethyloctane, the compound ‘X’ is
(a) CH3(CH2)3Br (b) CH3(CH2)5Br
(c) CH3(CH2)3CH(Br)CH3 (d) CH3–(CH2)2–CH(Br)–CH2CH3
Q3. Cycloalkane formed when 1, 4-dibromopentane is heated with sodium is
(a) methylcyclobutane (b) cyclopentane (c) cyclobutane (d) methylcyclopentane
Q4. Isobutyl magnesium bromide with dry ether and absolute alcohol gives
(a) CH3 C HCH2 OH & CH3CH2MgBr (b) CH3 C HCH2 CH 2CH 3 & Mg(OH)Br
| |
CH3 CH3

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 Anjana Chemistry Classes SCO-41, Top floor Sec 20 C, Chandigarh ,9464010111;
(c) CH3 C H CH 3 , CH 2  CH 2 & Mg(OH)Br (d) CH3 C HCH3 & CH 3CH 2OMgBr
| |
CH3 CH3

Q5. For preparation of alkanes, concentrated solution of Na or potassium salt of saturated acid is subjected to
(a) hydrolysis (b) oxidation (c) hydrogenation (d) electrolysis
Q6. Which following alkyl bromides may be used for the synthesis of 2, 3-dimethyl butane by Wurtz reaction?

Br Br
(a) (b) (c) Isobutyl bromide (d) s-butyl bromide
Q7. The reactivity of alkyl halides for Wurtz reaction is:
(a) 1o> 2o> 3o (b) 3o> 2o> 1o (c) 2o> 3o> 1o (d) 1o> 3o> 2o
Na/EtOH
Br Br Product:
Q8. 100oC
Br
(a) (b) (c)
(d) H2C = C = CH2
Q9. Which of the following can be prepared by Wurtz reaction?
(a) CH3CH3 (b) CH3CH2CH2CH3 (c) H 3 C  C H  CH 3 (d) CH 3  CH 2  C H  CH 3
| |
CH3 CH3
CH3
|
Na / ether
Q10. CH 3  C  Br    Major product:
| 
CH3
CH3 CH3 CH3
C H3 |
/ | |
(a) H2C  C (b) CH 3  C  C  CH 3 (c) CH 3  C  CH 2 CH 3 (d) No reaction
\ | | |
CH3
CH3 CH3 CH3
Q11. Which of the following compounds is most reactive wurtz reaction?

Br Br
Br
| CH3
(a) CH 3  C H 2  CH 3 (b) (c) (d) |
CH 3  C  Br
|
CH3

Q12. Which of the following fuel cause the lease pollution?

(a) Petrol (b) CNG (c) Kerosene (d) LPG
Q13. Which of the following gas is find in coal mines and marshy places?
(a) Methane (b) Ethane (c) Benzene (d) Propane
Q14. Two adjacent members of a homologous series have
(a) a difference of CH2 in their structure (b) a different of 14 amu in molecular mass
(c) same general method of preparation (d) All the above
Q15. The number of chain isomers possible for the hydrocarbon C5H12 is
(a) 1 (b) 2 (c) 3 (d) 4
Q16. The number of primary, secondary and tertiary carbons in 3, 4-dimethylheptane are respectively
(a) 4, 3 and 2 (b) 2, 3 and 4 (c) 4, 2 and 3 (d) 3, 4 and 2
Q17. Which of the following statements is false for isopentane
(a) it has three CH3 groups (b) It has one CH2 group
(c) it has one CH group (d) it has a carbon which is not bonded to hydrogen
Q18. Sodium sals of carboxylic acids on heating with soda lime give alkanes containing _______ than the
carboxylic acid

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 Anjana Chemistry Classes SCO-41, Top floor Sec 20 C, Chandigarh ,9464010111;
(a) one carbon more (b) one carbon less (c) two carbon less (d) Either (a) or (b)
Br
Mg
Product:
dryether
Q19. Br
(a) Br MgBr (b) BrMg MgBr
(c) CH3  CH = CH2 (d)
Q20. Which of the following alkyl halides is not suitable for Corey-House synthesis of alkanes?

(b) Br (c) I (d)

(a) CH3I Br

Q21. In order of get propane gas which of the following should be subjected to sodalime decarboxylation
(a) Sodium butyrate (b) Sodium propionate
(c) Mixture of sodium acetate and sodium ethanoate (d) Sodium formate
Q22. Domestic cooking gas consists of mostly
(a) Methane and ethane (b) Liquefied butane and isobutane
(c) Ethylene and carbon monoxide (d) Acetylene and hydrogen
Q23. The Kolbe’s electrolysis proceeds via
(a) Nucleophilic substitution mechanism (b) Electrophilic addition mechanism
(c) Free radical mechanism (d) Electrophilic substitution reaction
Q24. A sample of 4 mg of a compound of molar mass 90 g mol-1 when treated with CH3 – MgI releases 2 mL of
gas at NTP. The number of active hydrogen per molecule is
(a) 1 (b) 2 (c) 3 (d) 4
Q25. Anti-knocking agent for unleaded gasoline is
CH3
CH3
(a) CH  C|  OH (b) | (c) BXT (d) All of these
3 CH 3  O  C CH 3
|
|
CH3 CH3
(TBA ) (MTBE)
Q26. Formation of free radical is easiest in:
(a) Br
(b) Cl
(c) F
(d) I
Q27. n-Butane is produced by monobromination of ethane followed by the Wurtz reaction. Calculate the
volume of ethane at NTP required to produce 55 g n-butane; if the bromination takes place with 90% yield
and the Wurtz reaction with 85% yield.
(a) 55.5 L (b) 24.3 L (c) 22.4 L (d) 49.9 L
Q28. Find the product:
Na
Br Cl Product,
dioxane

(a) Cl Cl (b) Br Br

(c) Br Cl (d)
Q29. The bond dissociation energy of the C – H bond for the compound
H 3C  H H 3 C  CH 2  H H 2 C  CH  CH 2  H
H
(P ) (Q ) (R )

decreases in the order: (S)

(a) P > Q > R > S (b) S > R > Q > P (c) S > P > Q > R (d) Q > P > S > R
Q30. Which of the following alkanes cannot be synthesized by the Wurtz reaction in good yield?

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

Q31. The treatment of CH3OH with CH3MgI releases 1.04 mL of a gas at STP. The mass of CH3OH added is

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 Anjana Chemistry Classes SCO-41, Top floor Sec 20 C, Chandigarh ,9464010111;
(a) 1.49 mg (b) 2.98 mg (c) 3.71 mg (d) 4.47 mg
Q32. Each of the following alkyl halide reacts with sodium metal in presence of ether to form alkane except
(a) CH3Cl (b) CH3CH2Cl (c) (d) (CH3)3CCl
CH 3  CH  Cl
|
CH3

Q33.

Q34. Hydrocarbon(A) reacts with bromine by substitution to form an alkyl bromide which by Wurtz reaction is
converted to gaseous hydrocarbon containing less than four carbon atoms. (A) is
(a) CH  CH (b) CH2 = CH2 (c) CH3 – CH3 (d) CH4
Q35. Which one among the following carbocations has the longest half – life?

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 DPP NO. – 2 HYDROCARBONS
PROPERTIES OF ALKANES

OBJECTIVE ASSIGNMENT
Q1. The final product of oxidation of a hydrocarbon is
(a) an acid (b) an aldehyde (c) H2O + CO2 (d) an alcohol
Q2. Regarding chlorination and bromination, which of the following statements is correct?
(a) Time of formation of transition is earlier in bromination as compared to chlorination
(b) Free-radical character of C atom is less in bromination than chlorination
(c) Chlorine is more selective than bromine
(d) Transition state more closely resembles products in bromination as compared to chlorination
Q3. In the halogenation of ethane, which of the following product is never formed?
(a) CH3  CH3 (b) CH2 = CH2 (c) CH3CHX2 (d) CH3  CH2 – CH3
Q4. Which of the following is expected to have the highest melting point?
(a) n-hexane (b) neo-pentane (c) 2-methyl pentane (d) 2, 2-dimethylbutane
Q5. Which of the following represents the correct reaction?
(a) CH4 + 2H2O 
Ni
CO2 + 4H2 (b) CH4 + H2O 
Ni
CO + 3H2
(c) CH4 + H2O  CH3OH + H2 (d) CH4 + H2O  HCHO + 2H2
Ni Ni

Q6. During the chlorination of methane to methyl chloride the propagation step is represented by
 
hv
(a) Cl – Cl  Cl + Cl (b) C H 3  C l 
 CH 3 Cl

(c) CH4 + Cl  C H 3 + HCl (d) Cl + Cl 
 Cl2
Q7. Iodination of alkane is carried out in the presence of
(a) Alcohol (b) HNO3 or HIO3 (c) Any reducing agent (d) Benzene
Q8. The correct order of boiling points of 2, 2-dimethyl-propane, 2-methylbutane and n-pentane is
(a) n-pentane > 2, 2-dimethylpropane > 2-methylbutane
(b) n-pentane > 2-methylbutane > 2, 2-dimethylpropane
(c) 2-methylbutane > n-pentane > 2, 2-dimethylpropane
(d) 2-methylbutane > 2, 2-dimethylpropane > n-pentane
Q9. Isomers of hexane, based on their branching, can be divided into three distinct classes as shown in the
figure.

The correct order of their boiling point is

(a) I > II > III (b) III > II > I (c) II > III > I (d) III > I > II
Q10. When n-hexane is heated with anhydrous AlCl3 and HCl gas, the major product obtained is
(a) 1-chlorohexane (b) 2-chlorohexane (c) 3-chlorohexane (d) hex-3-ene
(e) mixture of 2-methylpentane and 3-methylpentane
V O ,500o C
Q11. n-C7H16    A Cl
2 5 / hv
2  B What is B in the above reaction?
10 20atm

(a) Benzyl chloride (b) Benzal chloride (c) Hexachlorobenzene (d) Benzene hexachloride
Q12. In the free radical chlorination of methane, the chain initiating step involves the formation of
(a) chlorine free radical (b) hydrogen chloride (c) methyl radical (d) chloromethyl radical
Q13. Photochemical halogenation of alkane is an example of
(a) electrophilic substitution (b) electrophilic addition
(c) nucleophilic substitution (d) free radical substitution
Q14. Which of these compounds represents the major monochlorination isomer formed in the following
reaction?
 Anjana Chemistry Classes SCO-41, Top floor Sec 20 C, Chandigarh ,9464010111;
CH3

Cl2
CH  CH3 Major
| hv monochlorination
CH3 isomer
CH3
CH3 CH3 CH3
Cl
Cl | Cl
(b) C  CH3
(a) CH  CH3
(c) CH  CH3 (d) CH  CH3
|
| | |
CH3 CH3
CH3 Cl CH3

Q15. Which one is the correct energy profile for Cl + Cl 
 Cl2?

(a) Energy (b)

Energy

Reaction co-ordinate
Reaction co-ordinate

Energy
(c) (d) All of these

Reaction co-ordinate

Q16. Which of the following is the free radical chain reaction?

 CH3CH3 + 2NaI
(a) 2CH3I + 2Na  (b) CH4 + Cl2 hv

 CH3Cl + HCl


(c) 2 CH 3 CO O N a  CH3CH3 + 2CO2 + 2NaOH + H2 (d) All of the above
Q17. Among the following incorrect statement(s) is/are:
(a) In alkanes the boiling point increases with a rise in molecular mass
(b) Branching in an alkane decreases the boiling point
(c) Boiling point of an odd numbered carbon atoms alkane is lower than both of its even numbered
neighbours
(d) Melting point of an odd numbered carbon atoms alkane is lower than next even numbered neighbours
Q18.
H
H3C CH3
Br2/hv
Products:
H H
H
CH3 CH3
| | Br Br
(a) H 3 C  C  CH 2 Br
(b) CH 3  C  CH 3
(c) (d)
| |
H Br
Q19.
Cr2O3  Al2O3
Major product:
600oC
CH3 CH3

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

Q20. Consider the following reaction:

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 Anjana Chemistry Classes SCO-41, Top floor Sec 20 C, Chandigarh ,9464010111;
D

+ Br 
 X + HBr
Identify structure of (X) among following:
D D D D

(a) CH2 (b)  (c) (d) 
 H2C
Q21. 2-Methylbutane on reacting with bromine in the presence of sunlight gives mainly
(a) 1-bromo-3-methylbutane (b) 2-bromo-3-methylbutane
(c) 2-bromo-2-methylbutane (d) 1-bromo-2-methylbutane
Q22. Arrange the following in decreasing order of their boiling points
(A) n – butane (B) 2-methylbutane (C) n-pentane (D) 2, 2-dimethylpropane
(a) A > B > C > D (b) B > C > D > A (c) D > C > B > A (d) C > B > D > A
Q23. Bromination of an alkane as compared to chlorination proceeds
(a) at a slower rate (b) at a faster rate
(c) with equal rates (d) with equal/different rate depends on the temperature
Q24. The slowest of abstraction of a hydrogen atom by a chlorine atom is shown by
(a) (CH3)3C – CH3 (b) (CH3)3 CH (c) C6H5CH3 (d) CH2 = CHCH3
Q25. The major product obtained when isobutane is treated with chlorine in the presence of diffused sun light is
(a) isobutylchloride (b) n-Butylchloride (c) tert-Butylchloride (d) sec-Butylchlroide
Q26. Ethane is subjected to combustion process. Hybrid state of carbon during the combustion changes from
(a) sp2 to sp3 (b) sp3 to sp (c) sp to sp3 (d) unpredictable
Q27. Which of the following is not an oxidation product of alkane?
(a) Alcohol (b) Aldehyde (c) Carboxylic acid (d) Ether
Q28. The reaction CH3 – CH2 – CH2 – CH3 Conc
. HCl
 CH  C H  CH is an example of
3 3
Anhyd. AlCl 3 |
CH3
(a) Isomerization (b) Polymerization (c) Cracking (d) Dehydrogenation
Q29. Propyl benzene with Cl2 in presence of light gives

* * *
Q30. Using *CH3I, which of the following is the best way to prepare C H3 C H2 C H3 ?
(a) *CH3I 1
. Li Cl2
  Na
 (b) *CH3I 1
. Li Cl2
  1
. Li

2. CuI hv ether 2. CuI hv 2. CuI
3. *CH3I 3. *CH3I
Na Cl Na Na Cl2
(c) *CH3I  
2
 (d) *CH3I   *
CH3I

ether hv ether ether hv Na / ether

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 DPP NO. – 3 HYDROCARBONS
PREPARATIONS OF ALKENES
SUBJECTIVE ASSIGNMENT
Q1. Draw the cis- and trans-structures for hex-2-ene. Which isomer will have higher b.p. and why?
Q2. Which of the following shows geometrical isomerism? Give the structures of its cis- and trans-forms.
(i) CHCl = CHCl (ii) CH2 = CCl2 (iii) CCl2= CHCl
Q3. Discuss briefly the isomerism in alkenes.
Q4. A hydrocarbon has the molecular mass 70. Write all the possible structural isomers and give their names.
Q5. Which of the following alkenes will show geometrical isomerism?
(i) Propene (ii) But-2-ene (iii) But-1-ene (iv) 2, 3-Dimethylbut-2-ene
Q6. How can ethene be prepared from (i) ethanol and (ii) ethyl iodide?
Q7. Explain the following with one example: (a) Dehydrohalogenation (b) Dehydration.
OBJECTIVE ASSIGNMENT
Q1. Bond angle in alkenes is equal to
(a) 120o (b) 109o28’ (c) 180o (d) 60o
Q2. Isopropyl alcohol is obtained by reacting which of the following alkenes with conc. H2SO4 and H2O
(a) Ethylene (b) Propylene (c) 2-methyl propene (d) Isoprene
Conc. H SO
Q3. The main product of the following reaction is C6H5CH2CH(OH)CH(CH3)2   
2
4 
CH CH(CH3 )2
(a) H5C6CH2CH2 \ C  CH (b) H5C6 \ C  C / H (c) C6H5CH2 \ C  C / 3 (d) C6H5 \ C  C /
\H
H3C / H/ \ CH
2
H / \ CH(CH )
3
H/
3 2
Na
Pd / C
Q4. A   CH 3 C  CCH 3 in
liquid
 NH
 B . A and B respectively are:
Catalyst 3

(a) A is cis while B is trans – 2- butene (b) A is trans while B is cis-2-butene

(c) A and B both are trans -2-butene (d) A and B both are cis-2-butene
Q5. Which one of the following heptanols can be dehydrated to hept-3-ene only?
(a) Heptan-3-ol (b) Heptan-4-ol (c) Heptan-2-ol (d) Heptan-1-ol
Q6. Arrange the following alkanols 1, 2 and 3 in order of their reactivity towards acid catalysed dehydration.
OH
OH |
(1) (2) | (3) (CH 3 ) 2 CH  C H CH 3
CH 3  C H  CH 2  C H 2 CH 3  C  CH 2  CH 3
| | |
CH3 OH CH3

(a) 1 > 2 > 3 (b) 2 > 1 > 3 (c) 2 > 3 > 1 (d) 3 > 2 > 1
Q7. What is the major product expected from the following reaction?
1 mol D
CH 3  C  C  CH 3   
2

Low pressure
poisoned catlyst
D D D D
(a) CH3 D (b) CH3 CH3 (c) | | (d) | |
CH 3  C  C  CH 3 CD 3  C  C  CD 3
C C C C | | | |
D CH3 D D D D D D
Q8. In 1, 2-elimination of HX
H X
C C +:B C=C

The electron pair of the newly formed -bond is provided by

(a) the lone pair of electrons present on the base B (b) the pair of electrons formation C  X bond
(c) the pair of electrons forming C  H bond (d) either of the three
Q9. The nodal plane in the -bond of ethane is located in
(a) the molecular plane (b) a plane parallel to the molecular plane
(c) a plane perpendicular to the molecular plane which bisects the carbon – carbon -bond at right angle
(d) a plane perpendicular to the molecular plane which contains the carbon – carbon -bond.
Q10. What is the order of dehydrohalogenation of the following compounds in presence of strong base?
Br
Br CH2Br CH3

Br
(1) (2) (3) (4)
(a) 1 > 2 > 3 > 4 (b) 2 > 4 > 3 > 1 (c) 4 > 2 > 1 > 3 (d) 1 > 2 > 4 > 3
Q11. Which is most easily dehydrohalogenated?

(I) Cl (II) Cl (III) Cl

(a) I (b) II (c) III (d) all with same case
 Anjana Chemistry Classes SCO-41, Top floor Sec 20 C, Chandigarh ,9464010111; [email protected]
Q12. The relative stability of the compounds given below is in the order.
CH3 CH3 CH 3
| | |
(I) CH 3  C  C  CH 3 (II) CH 3  C  CH  CH 3 (III) CH3 – CH = CH2 (IV) CH2 = CH2
(a) I > II > III > IV (b) IV > III > II > I (c) I > III > II > IV (d) II > I > IV > III
Q13. The product can be:
Br

CH3
Heat /alc.
CH3 KOH Product

CH3
CH3 CH3 CH3 CH3
(a) CH3 (b) CH3 (c) (d)
CH3
Q14. Consider the following reaction.
CH3
| CH3 CH3 CH2 CH3
base \ / /
CH 3  C  CH 2 CH 3  CC  CH 2  C
| / \ \
CH3 H CH3
Br (I ) ( II )

Which of the following base will give the best yield of the alkene II as the major product?
(a) CH3O (b) C2H5O (c) (CH3)3CO (d) (C2H5)3CO
Q15. Dipole moment of which compound will be maximum?
H3C H H3C H H H H H
(a) (b) (c) (d)
H Cl H H H Cl H H
Q16.
Conc. H3PO4
CH2  OH Major product:


(a) CH2 (b) (c)

CH3 (d)
Q17. Br \ Br
CH  CH /  
Zn , dust

Br / \ Br 

Br Br \
(a) \ /H (b) / Br (c) H – C  C  H (d) /
Br
CC CC CH 3  CH
/ \ / \ \
H Br H H Br
Q18. Dehydrohalogenation in presence of OH is correctly represented by

Br Br Br OH Br

(a) (b) (c) (d) OH

H H H H
OH OH
Q19. Which product is formed when the following alcohol is heated with sulphuric acid?
CH2OH

H+

CH3

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

Q20. The product is correctly shown as

Ph Ph
CH3CH2O
Br Br
H Ph
Ph Ph Ph H Ph Br Ph Ph
(a) C=C (b) C=C (c) C=C (d) C=C
Br Ph Br Ph Ph H H H
H H
Q21. In the carbocation 1 2 |  |4 5 the species H/CH3 that is most likely to migrate positively charged carbon
H 3 C C  C  C C H 3
| | |
OH H CH 3
is
(a) CH3 at C – 4 (b) H at C  4 (c) CH3 at C – 2 (d) H at C – 2

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 DPP NO – 4 HYDROCARBONS
PROPERTIES OF ALKENES

OBJECTIVE ASSIGNMENT

CH3CH = CH OH
Q1. The reaction of with HBr gives
(a) CH3CHBrCH2 OH (b) CH3CH2CHBr OH

(c) CH3CHBrCH2 Br (d) CH3CH2CHBr Br

Q2. Reaction of one molecule of HBr with one molecule of 1, 3-butadiene at 40oC gives predominantly
(a) 3-bromobutene under kinetically controlled conditions
(b) 1-bromo-2-butene under thermodynamically controlled conditions
(c) 3-bromobutene under thermodynamically controlled conditions
(d) 1-bromo-2-butene under kinetically controlled conditions
Q3. The compound formed when 2-butene is treated with hot alkaline KMnO4 is:
(a) Acetaldehyde (b) Acetic acid (c) CH2OH . CH2OH (d) CH3 . CH2 . CO . CH3
Q4. An organic liquid (A), containing C, H and O with the boiling point 78oC and possessing a rather pleasant
odour, or heating with concentrated H2SO4 gives a gaseous product (B) with the empirical formula CH2.
(B) decolourises bromine water as well as alkaline KMnO4 solution and takes up one mole of H2 (per mole
of B) in the presence of finely divided nickel at high temperature. (A) and (B) are:
(a) C2H5OH, C2H2 (b) CH3OH, C2H5 (c) C2H5OH, C2H4 (d) (CH3)2CHOH, C3H6
Q5. 2-methyl propene is isomeric with But-1-ene. They can be distinguish by:
(a) Baeyer’s reagent (b) Ammonical AgNO3 (c) Br2 solution (d) O3, Zn/H2O
Q6. Which alkene on oxidation with acidic KMnO4 gives only acetic acid?
(a) CH3 = CH – CH3 (b) CH3 – CH = CH – CH3
(c) Ethylene (d) Pentene – 2

HBr
H3C  O CH = CH – CH3 Major product:
Q7.
Br Br
| |
(a) H3C  O CH2  CH – CH3 (b) H3C  O CH  CH2 – CH3

(c) Both (a) and (b) in same amount (d) None of the above
Q8. The mechanism of the reaction of propene with HOCl (Cl2 + H2O) will proceed through which of the
following intermediates?
OH Cl
  |  | 
(a) CH 3  C H  CH 2  OH (b) CH 3  C H  CH 2  Cl (c) CH 3  C H C H 2 (d) CH 3  C H C H 2

Q9. The decreasing order of reactivity of following alkenes for hydrogen bromide is
(CH3 )2 C  CH2
IV

(a) I > III > II > IV (b) IV > II > I > III (c) III > I > II > IV (d) II > IV > I > III
Q10. The rate – determining step in the following reaction is CH2=CH2 + HOCl  CH2OHCH2Cl
(a) addition of OH (b) addition of OH+ (c) addition of Cl+ (d) addition of Cl
Q11. If heat of hydrogenation of 1, 3-pentadiene and 1, 4-pentadiene and X and Y kcal respectively, heat of
hydrogenation of 2, 3-pentadiene will be
 Anjana Chemistry Classes SCO-41, Top floor Sec 20 C, Chandigarh ,9464010111;
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(a) between X and Y (b) less than X as well as Y (c) greater than X as well as Y (d) It can’t be predicted

Alk. KMnO4

Q12. The product of this reaction is

CH2OH CH2OH CH2OH

(a) (b) (c) (d) OH

OH OH
OH
Q13. Compound A(C6H10) absorbs one mole of hydrogen during catalytic hydrogenation , its ozonolysis give
hexan – 2, 5-dione. Compound A is
(a) 1, 3-dimethyl cyclohexene (b) 1, 2- dimethyl cyclobutene
(c) 1, 2-dimethyl cyclopentene (d) 1, 2-dimethyl cyclopropane
Q14. The preparation steps involved in the free radical addition of HX across a double bond are:
| | | | | |
\ /
Step 1: CC X 
 X  C C' Step 2: X  C C'H  X 
 X  C C H  X'
/ \ | | | | | |

HCl does not follow free radical addition because

(a) both steps are exothermic (b) both steps are endothermic
(c) step-1 is exothermic and step -2 is endothermic (d) step – 2 is exothermic and step – 1 is endothermic

Q15. Identify A and B in the reaction sequence. CH 3  C H  CH  CH 2  HBr 

 ( A ) + Alc. KOH → [B]
|
CH3
Br
|
(a) A = (CH ) C CH  CH , B  CH  C  CH  CH (b) A  (CH3 )2 CH  C H CH3 , B  (CH3 )2 CH  CH  CH2
3 2 2 3 3 3
| |
Br CH3
Br
|
(c) A  (CH ) C CH CH , B  H C  C CH  CH (d) A  (CH3 )2 CH  C H CH3 , B  (CH3 )2 CH  CH  CH2
3 2 2 3 2 2 3
| |
Br CH3
Q16. 2-phenylpropene on acidic hydration gives
(a) 2-phenyl-2-propanol (b) 2-phenyl-1-propanal (c) 3-phenyl-1-propanol (d) 1-phenyl-2-propanal
CH3 CH3
| |
Q17. NaIO 4
CH 3  C  CH  C  CH 3    Products , The product are:
| KMnO 4
CH3
O O O O
|| || || ||
(a) CH 3  C  OH' (CH 3 ) 3 C  COOH (b) CH 3  C  OH' (CH 3 ) 3 C  COOH (c) CH 3  C  CH 3 , (CH 3 ) 3 C  COOH (d) CH 3  C  CH 3 , (CH 3 ) 3 C  CHO
Q18. The reaction of ethylene with Br2 in water in the presence of NaCl gives:
(a) 1, 2-dibromoethane (b) 2-bromoethanol (c) 1-bromo-2-chloroethane (d) all of these
Q19. A hydrocarbon C8H14 consumes only one mole of H2 on catalytic hydrogenation.
The hydrocarbon when heated with hot and concentrated alkaline KMnO 4 gives cyclohexanone and acetic
acid (after acidification). The hydrocarbon is:
(a) 1-ethylcyclohexene (b) 1, 2-dimethylcyclohexene (c) ethylidenecyclohexane (d) cyclohexylethene
Q20. A and B are
H2 O3/H2O
A B
1 eqiv.

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 Anjana Chemistry Classes SCO-41, Top floor Sec 20 C, Chandigarh ,9464010111;
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(a) , (b) , not formed
HOOC COOH

(c) , (d) None is correct

OHC CHO
Q21. Arrange the following reactions in decreasing order of electrophilic addition reaction:
CH3 \ CH3 \ CH3 \
HCl HCl HCl
C  CH 2  C  CH 2  C  CH 2 
/  /  /
CH3 (P ) CH3 O CH3 N H
(Q) (R )

(a) P > Q > R (b) Q > R > P (c) R > Q > P (d) P = Q = R
Q22. Rates of hydrohalogenation of the following alkenes are:
CH = CH CH3  CH = CH

(P) (Q)
CH3
|
CH 3  C  CH  CH 2 CH 3  CH  CH  CH 3
|
CH3 (S )
(R )
(a) P > Q > R > S (b) Q > P > R > S (c) Q > P > S > R (d) P > Q > S > R
Q23. When one mole of an alkene on ozonolysis produces 2 moles of propanone, the alkene is
(a) 3-methyl-1-butene (b) 2, 3-dimethyl-1-butene (c) 2, 3-dimethyl-2-pentene (d) 2, 3-dimethyl-2-butene
Q24. Which alkene on oznolysis gives CH3CH2CHO and CH 3 C CH 3
||
O
CH3
(a) CH 3CH 2 CH  C /\ (b) CH3CH2CH = CHCH2CH3 (c) CH3CH2CH = CHCH3 (d) CH 3  C  CHCH 3
CH3 |
CH3

X
Q25. In the given reaction CH3CH2CH = CHCH3  CH 3 CH 2 COOH  CH 3 COOH The X is

(a) C2H5ONa (b) Conc. HCl + Anhy ZnCl2 (c) Anhy. AlCl3 (d) KMnO4/OH
Q26. Isopropyl alcohol is obtained by reacting which of the following alkenes with conc. H 2SO4 and H2O
(a) Ethylene (b) Propylene (c) 2-methyl propene (d) Isoprene
Q27. The most reactive alkene HBr among the following is
(a) (CH3)2C = C(CH3)2 (b) CH2 = CH2 (c) (CH3)2C = CH2 (d) CH3CH = CHCH3
Q28. Addition of HBr to 2-methyl-prop-1-ene in the presence of hydrogen peroxide mainly forms
(a) 1-Bromobutane (b) 2-Bromopropane (c) 2-Bromo-2-methylpropane (d) 1-Bromo-2-methylpropane
Q29. Oxidation of 1-butene with hot KMnO4 solution produces
(a) CH3CH2COOH + HCOOH (b) CH3CH2COOH + CO2 (c) CH3COOH + CO2 (d) (CH3)2C = O + CO2
Q30. Ethene gas is bubbled through the water saturated with chlorine. The major product formed will be
(a) Ethanoyl chloride (b) Ethylene chlorohydrin (c) Ethylene chloride (d) Ethylene glycol
Q31. Which of the following reagent cannot be used for the oxidation of propene?
(a) KMnO4/KOH (b) C6H5CO2OH (c) Fehling solution (d) Ozone
Q32. In which of the following reactions Markownikov’s rule is not observed
Organic peroxide Organic peroxide
(a) CH3CH = CH2 + HCl     
 (b) CH3CH = CH2 + HBr     

Organic peroxide Organic peroxide
(c) CH3CH = CH2 + HI     
 (d) CH3CH = CH2 + H2SO4     


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 Anjana Chemistry Classes SCO-41, Top floor Sec 20 C, Chandigarh ,9464010111;
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Q33. Which of the following will be the main product for the chlorination of propylene at 750 K?
(a) CH2ClCH = CH2 (b) CH3CH2Cl . CH2Cl (c) CH2ClCH = CHCl (d) CH  CH  CH
2 2
| | |
Cl Cl Cl
X
Q34. (CH3)2C = CHCH3  Acetone + AcOH. In the above reaction X is
Heat
(a) KMnO4/H2SO4 (b) O3 (c) C6H5COOH (d) O2
Q35. An alkene upon ozonolysis yield CHO – CH2 – CH2 – CH2 – CHO only. The alkene is

(a) CH2 = CH – CH2 – CH2 – CH2 – CH2 – CH3

Q36. Reductive ozonolysis of o-xylene gives
(a) Glyoxal (b) Methyl glyoxal (c) Dimethyl glyoxal (d) All the above
Q37. A compound A with molecular formula C6H10 on oxidation with hot KMnO4 gives hexandioic acid. A is
(a) 2-Hexyne (b) 1, 5-Hexadiene (c) 1, 3-Hexadiene (d) Cyclohexene
Q38. Consider the addition of HBr to 1, 3-butadiene:
I. Markownikoff addition occurs, producing the allylic carbocation.

II. 3-bromo-1-butene from (X) is the kinetic product.

III. cis-1-bromo-2-butene from (Y) is the thermodynamics product. Select the correct statements
(a) Only I and II (b) Only II and III (c) Only I and III (d) I, II and III
Q39. Correct order of reactivity towards electrophilic addition reactions is:
(a) CH2 = CH2 > CH2 – CH = CH2 > (CH3)2C = CH2 (b) CH2 = CH2 < CH3  CH = CH2 < (CH3)2C = CH2
(c) CH2 = CH2 < (CH3)2C = CH2 < CH3  CH = CH2 (d) CH3 – CH = CH2 < CH2 = CH2 < (CH3)2C = CH2
Q40. Propene is more reactive than ethene towards HBr because
(a) propene can more readily undergo a free radical chain reaction
(b) propene gives rise to more stable carbocation (c) the double bond in case of propene is unstable
(d) the methyl group attached to double bond withdraws electrons and facilitates the attack
Q41.
HBr
A

B
CH3CH2CH3

(a) Compound A is (b) Compound A is H3C  CH2 – CH2 – Br

Br
(c) Reagent B is H2/Ni at 120oC (d) Reagent B is LiAlH4

INTEGER ANSWER TYPE

Q42. Total number of organic products obtained from ozonolysis of cyclopentene is
Q43. For the given reaction how many products will obtain (all isomers)?
Br2/hv

Q44. Number of optically active products (not isomers) possible from the monochlorination of
CH3
is

4
 DPP NO – 6
HYDROCARBONS

OBJECTIVE ASSIGNMENT (ALKYNES)

Q1. The reaction of cyclo-octyne with HgSO4 in the presence of aqueous H2SO4 gives
O
OH OH
(a) (b) (c) (d)
OH OH

Q2. When but-1-yne is treated with excess of HBr, the expected product is
(a) 1, 2-Dibromobutane (b) 2, 2-Dibromobutane (c) 1, 1-Dibromobutane (d) All the above
Q3. But-1-yne can be converted into 1-bromo-1-butene by reacting it with which of the following reagent?
(a) HBr (b) HBr and (C6H5COO)2 (c) Br2 and H2O2 (d) Br2 and CCl4
Q4. The hydrocarbons which gives benzene on passing through a red hot iron tube is
(a) CH4 (b) C2H2 (c) C2H4 (d) C2H6

Q5.  CHCNa++NH3 shows that hydrogen atom of terminal acetylene are

The reaction CHCH + NaNH2 
(a) acidic (b) Basic (c) Neutral (d) Amphoteric
2
Ba
Q6. Ethyne + X  Prop-2-ene-nitrile. Here X can be
(a) Bromine (b) Barium cyanide (c) Hydrogen bromide (d) Hydrogen cyanide
Q7. Which of the following alkynes will not be able to show acidic character?
(a) 1-Butyne (b) 2-Butyne (c) Propyne (d) Ethyne
Q8. The reagent(s) required to convert 1-butyne to 2-butanone is (are)
(a) dilute H2SO4 (b) ZnCl2 + HCl (c) Hg2+ + H2SO4 (dilute) (d) Alk. KMnO4
Q9. Which is the weakest acid among the following?
(a) HCl (b) Acetylene (c) Phenol (d) Picric acid
Q10. Propyne on passing through red hot copper tube forms
(a) Benzene (b) Toluene (c) Mesitylene (d) None
Q11. When CH3[CH2]3C  CH is oxidized with hot alkaline KMnO4 the product is
(a)CH3CH2COOH (b)CH3CH2CH2COOH (c)CH3CH2CH2COOH&CO2 (d)CH3CH2CH2CH2COOH&CO2
Q12. When but-2-yne is ozonized the product is
(a) Glyoxal (b) Methyl glyoxal (c) Dimethyl glyoxal (d) Acetone

Q13. What is X in the following reaction?

Q14. Which of the following ketones cannot be formed by hydration of a suitable alkyne?
(a) Propanone (b) Butan-2-one (c) Pentan-2-one (d) Benzophenone
Q15. Ethylidene chloride is formed by treating acetylene with:
(a) HCl (b) Cl2 in the presence of CCl4 (c) HOCl (d) Cl2 in presence of organic peroxide
Q16. Acetylene gives
(a) White ppt, with ammonical AgNO3 and red ppt. with ammonical Cu(NO3)2

1
 Anjana Chemistry Classes SCO-41, Top floor Sec 20 C, Chandigarh ,9464010111;
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(b) White ppt. with ammonical AgNO and red ppt. with ammonical Cu Cl
3 2 2

(c) White ppt. with both (d) Red ppt. with both
Q17. Which is most suitable reagent among the following to distinguish compound(3) from rest of the
compounds?
(1) CH3C  C – CH3 (2) CH3CH2 – CH2 – CH3 (3) CH3CH2C CH (4) CH3CH2 -CH3
(a) Bromine in carbon tetrachloride (b) Bromine in acetic acid solution
(c) Alk. KMnO4 (d) Ammonical silver nitrate
Q18. Bond length of Ethane (I), Ethene (II), Acetylene (III) and Benzene (IV) follows the order
(a) I > II > III > IV (b) I > II > IV > III (c) I > VI > II > III (d) III > IV > II > I
Q19. Which one of the following compounds will react with methylmagnesium iodide?
(a) CH3CH2CH2CH2CH3 (b) CH3CH=CH–CH=CH2 (c) CH3–CC–CH2CH3 (d) CH3CH2CH2CCH
Q20. Two organic compounds A & B both containing only carbon & hydrogen, on quantitative analysis gave
same percentage composition by weight: C = (12/13)  100%, H = (1/3)  100%. A decolourizes Br2 water
but B does not. A & B respectively are
(a) C2H2 and C6H6 (b) C6H6 and C2H2 (c) C2H4 and C2H6 (d) C2H2 and C2H6
Q21. When 2-pentyne is treated with dil. H2SO4 and HgSO4, the product formed is
(a) 1-pentanol (b) 2-pentanol (c) 2-pentanone (d) 3-pentanone
Q22. When CH3CH2CHCl2 is treated with NaNH2 the product formed is
NH2 Cl
(a) CH3CH – CH2 (b) CH3 – C  CH (c) CH 3 CH 2 CH / (d) CH 3 CH 2 CH /
\ \
NH2 NH2
Q23. The no. of structural & configuration isomers of a bromo compound, C 5H9Br formed by addition of HBr to
2-pentyne respectively are:
(a) 1 and 2 (b) 2 and 4 (c) 4 and 2 (d) 2 and 1
Q24. Among the following compounds, the strongest acid is
(a) HC  CH (b) C6H6 (c) C2H6 (d) CH3OH
Q25. The hydrocarbon which can react with sodium in liquid ammonia is
(a) CH3CH2CCCH2CH3 (b) CH3CH2CH2CCCH2CH2CH3 (c) CH3CH2CCH (d) CH3CH=CHCH3
Q26. The correct order of increasing basicity of the given conjugate bases (R = CH3) is
(a) RCOO < HC  C < NH2 < R (b) RCOO < HC  C < R < NH2
(c) R < HC  C < RCOO < NH2 (d) RCOO < NH2 < HC  C < R
HI
Q27. Predict the product C in the following reaction of butyne-1 CH3CH2–C  CH +HCl 
 B  C

I I I
| | |
(a) CH 3 CH 2  C  CH 3
(b) CH  C H  CH CH I (c) CH  CH  CH  C H (d) CH 3  CH 2  C H  CH 2 Cl
3 2 2 3 2 2
| | |
Cl Cl Cl

Q28. What is the product formed when acetylene reacts with excess of hypochlorous acid?
(a) CH3COCl (b) ClCH2CHO (c) Cl2CHCHO (d) ClCH2COOH
Q29. A compound X (C5H8) reacts with ammoniacal AgNO3 to give a white precipitate, and on oxidation with
hot alkaline KMnO4 gives the acid, (CH3)2CHCOOH. Therefore, X is
(a) CH2 = CHCH = CHCH3 (b) CH3(CH2)2C  CH (c) (CH3)2CH – C  CH (d) (CH3)2c = C = CH2
Q30. Identify the reagent from the following list which can easily distinguish between 1-butyne and 2-butyne

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 Anjana Chemistry Classes SCO-41, Top floor Sec 20 C, Chandigarh ,9464010111;
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(a) bromine, CCl4 (b) H2, Lindlar catalyst (c) dilute H2SO4, HgSO4 (d) ammoniacal Cu2Cl2 solution .
Q31. The order of relative acidic strength of water, ammonia and acetylene is
(a)Water>ammonia>acetylene (b)Ammonia>water>acetylene
(c)Water>acetylene>ammonia (d)Acetylene>water>ammonia
MATCH THE FOLLOWING:
Q32. Match column – I with column – II.
COLUMN – I COLUMN – II
(A) CH3COCH3 
 CH3CH2CH3 (P) Sodalime

(B) CH3CH2Br 
 CH2 = CH2 (Q) Zn dust

(C) C6H5COOH 
 C6H6 (R) KOH (alc.)

(D) C6H5OH 
 C6H5 (S) HI/red P

Q33. CH3C  CNa + D2O  A + B. The product A in the reaction is

(a) CH3  C  C  C  C  CH3 + NaOD (b) CH3C  CD + NaOD
(c) CH3CH=CD + NaOD (d) CH3  C  C  CH3 + NaOD
 
COO K Electrolysis
Product:
 
Q34. COO K

(a) (b) (c) (d) None of these

H3C
Q35. \ / Br 
 H3CCC–CH3 Which of the following reagents can be used for above conversion?
CC
/ \
Br CH3

(a) Zn/ (b) Mg/ (c) NaI/acetone (d) Alc. KOH

Q36. The correct basicity orders are:
       
(a) CH 3  C H 2  H 2 C  C H (b) CH 3  C H 2  H 2 C  C H (c) CH 3  C H 2  HC  C (d) H 2 C  C H  H  C  C

Q37. But-2-yne on chlorination gives

(a) 1-chlorobutane (b) 1, 2-dichlorobutane (c) 1, 1, 2, 2-tetrachlorobutane (d) 2, 2, 3, 3-tetrachlorobutane
A B
Q38. In the given reactions CH3C  CH  CH3CBr2CHBr2 CH3C  CH  CH3CBr2CH3
Hg 2 / H  Hg 2 / H 
CH3C  CH   C HC  CH   D A, B, C and D are respectively
333K 333K

(a) HBr, Br2, CH3COCH3, CH3CHO (b) Br2, HBr, CH3COCH3, CH3CHO
(c) HBr, HBr, CH3COCH3, CH3CHO (d) Br2, HBr, CH3CH2CHO, CH3CHO

Q39. Identify Z in the following reaction sequence CH3CH2CH2OH conc

 . H2SO4
  X Br
2
Y alc
. KOH

 Z
o
160180 C

(a) CH3 – CH(NH2) – CH2NH2 (b) CH3 – CH(OH) – CH2OH (c) CH3 – C(OH) = CH2(d) CH3 – C  CH