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Page # 57 HYDROCARBON

REACTION CHART FOR ALKANES


GMP

H2 , Ni X 2 , h or UV light or 400 C
(1) R – C  CH    (1)              RX
200  300 C
or
R – CH = CH2 Sabatier senderens Re ed reaction
(2) SO2 + Cl2     RSO2Cl
reaction h
Zn  Cu  HCl
(2) R–X      
Re d P  Hi, LiAlH 4
AlCl3 / HCl
(3)      branched alkanes
HOH or ROH Isomerisation
(3) R–Mg–X       

or NH3 or RNH2
R–H Pyrolysis
Na, dry ether or (4)     
 Alkenes + CH4 or C2H6
(4) RX       500  700 C
Wurtz reaction R–R
or
(5) Re d P / HI
R – C – Cl or ROH  CnH2n+2
   
O
or
R – C – R or RCHO

Zn  Hg / Conc. HCl
(6) R–C–R         
Clemension' s reduction
O

2 2
H N  NH ,HO , 
(7) R – C – R 

Wolf / Kishner reduction
O
or

(RCH2CH2)3B H O
 2


(8) RCOONa NaOH  CaO


     

(9) Kolbe' s electrolytic synthesis


RCOONa   

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Page # 58 HYDROCARBON

REACTION CHART FOR ALKENES


GMP GR
conc. H SO4 H2 , Ni
(1) R–CH2–CH2–OH   2  
 (1)       R–CH –CH
 H2O 200  300 C 2 3

alc. KOH X2
(2) R–CH2–CH2–X    (2)  
 R–CHX–CH2X
 HX

HX
(3)   R–CHX–CH3

Zn dust R–CH=CH2
(3) R–CH2–CH      
or
for higher alkene
CnH2n HBr , Peroxide
(4) 
 X2   R–CH2–CH2Br

HOCl
(5) 
(4) R – CH – CH2 Zn dust  R–CH(OH)–CH2Cl

   
X X
dil. H2SO4
(6)     R–CH (OH)–CH
2 3
 H2O
Ni, H2
(5) R–C  CH     

200  300C
BH3
(7)   (RCH2CH2)3B
RCH — COOK Kolbe' s electrolytic synthesis
(6)          
RCH — COOK O2
(8)  
 CO + H O
2 2

(7) (C2H5)4N+OH 

OS O 4
(9)   R – CH – CH2
(8) R–C–O–CH 2–CH 2–R Pyrolysis
   OH OH
O
Bayer reagent
(10)        R – CH – CH2
1% alkaline KMnO 4
OH OH

R H
O 3 H2O C+C
(11)    
Ozonolysis
H H
O O

394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
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HYDROCARBON Page # 59

394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
IVRS No. 0744-2439051, 0744-2439052, 0744-2439053, www.motioniitjee.com, email-info@motioniitjee.com
Page # 60 HYDROCARBON

Exercise - I (Only one option is correct)


H
Br
CH3 CH3
Br2,hv
1. Major Product
Na (A)
3.
H H D.E
H

CH 3 CH 3 Br
| |
(A) CH3—CH—CH2Br (B) CH3—CBr—CH3
Br
| (A) (B)
(C) CH 3CH 2CH 2Br (D) CH3—CH—CH3
Sol.

(C) (D)

Sol.

Br

Na (A) Major product (A) is :


2. Br
D.E
Na (A)
4.
D.E
(A) (B) Cl

(A) (B)
(C) (D)
Sol.

(C) (D)

Sol.

394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
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HYDROCARBON Page # 61

Br O
Na (A) se (B)
5. N 2 H4 KOH
D.E
7. (A) (B)
Br
Product (B) will be :
Product (B) will be :

(A) (B)
(A) (B)

Br
OH
CH3
(C) (D)
(C) (D)

Sol.
Sol.

CH3 Zn(Hg)
6. (A)
HCl
Cl2
8. (A). Product (A) will be :
(Major) Product (A) will be : hv
CH3
Cl

(A) (B)
(A) (B)

OH

(C) (D) (C) (D)

Sol.
Sol.

394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
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Page # 62 HYDROCARBON

Cl2 Sol.
9. n-Pentane (A)
hv
(A) 2 (B) 3
(C) 4 (D) 5
Sol.

Cl
Na
13. Dry ether ?
Cl2 Cl
10. CH3—CH—CH2—CH2—CH3
| hv
CH3
(A)
Mono-chloro product (inculding steroisomers)
are :
(A) 6 (B) 7
(C) 8 (D) 9
Sol.
(B)

(C)

11. CH3 CH3 ?


Na
Cl
Dry ether
Cl Cl
CH3
CH3 CH3
(D)
(A) CH3 (B)
Cl
CH3 Sol.
CH 3
(C) (D)

CH3
Sol.

14. Methyl cyclohexene react with Br2 in pres-


ence of u.v. light major product will be

Br
Na (A) (B)
12. CH3 — Cl + CH3 — CH2 — Cl
Dry ether Br
products.
Which of the following is not the free radical
combination product in wurtz process. Br
(C) (D)
(A) CH3 — CH3
(B) CH3 — CH2 — CH3
(C) CH3 — CH2 — CH2 — CH3 (D) CH4
Br

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HYDROCARBON Page # 63

Sol.
Na
16. * Cl ?
Dry ether

Possible prodcuts are :(C = C14)

(A) * *

Br2 Na
15. (A) (B) (B) is (B)
h.v. DMF

* *

(C) *

(A) *
(D) All of these
Sol.

(B)
Na
17. (i) Br
D.E

(ii) Na
F
D.E

(iii) Na
Cl
D.E

(iv) Na
I
(C) D.E
Correct order of rate of reaction will be
(A) iv > iii > i > ii (B) iii > iv > i > ii
(C) iv > i > iii > ii (D) None of these
Sol.
(D) None of these
Sol.

394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
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Page # 64 HYDROCARBON

+ – electrolysis
20. X 2, 3-dimethyl butane
Which of the following anion will be migrates
18.
towards anode to prepare 2, 3-dimethyl
butane in the given reaction.
O

(A)
CH3COOK O
+
Et COOK O
(B)
Which of the gases evolved on the surface of O
anode. O
(A) C2H6, H2 (C)
(B) C3H8, H2 O
(C) C2H6 + C4H6 + CO2 O
(D) C2H6 + C4H10 + CO2 
Sol. (D) O
Sol.

O –
NH2NH2+OH /
21. Most stable
O O
confomer of product will be (across C2 — C3
OH bond) :
19.  (A) gauche (B) Anti
(C) Eclipsed (D) Partially eclipsed
Sol.
O

OH

Suitable reagent for following cenversion will O


be : Zn-Hg+HCl
(A) Zn – Hg + HCl (B) Mg(Hg) 22. most stable
(C) H—Br (D) All of these confomer of product will be :
Sol.
H H H
H H

(A) (B)
Et
H H H H H
Et
H H H

H H
(C) (D)
Me
H H H H H
Me

394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
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HYDROCARBON Page # 65

Sol. Sol.

* O
Zn—Hg + HCl (excess)
26. O
14
(*C=C )
product will be :
* O
CH3 (A) (B)
H H *
H H H H H H
* O
(C) * (D)
23.
CH3 CH3 H H CH3 CH3 Sol.
H H CH3

(I) (II) (III)


Correct order of mono bromination of given
compound is :
(A) I > III > II (B) I > II > III (C) II > I > III
(D) III > II > I
Sol.
27. Rate of decarboxylation of following carboxy-
lic acid with sodalime will be in order
NaOH+CaO
CH3COOH
r1
NaOH+CaO
CH3CH2COOH
r2
O CH 3
| NaOH+CaO
— + CH3 — CH — COOH
ONa Electrolysis r3
24. — + major product
ONa (A) r1 > r2 > r3 (B) r3 > r2 > r1
(C) r2 > r3 > r1 (D) r1 > r3 > r2
Sol.
O
will be
(A) 1-butyne (B) n-butane
(C) 2-butene (D) 2-butyne
Sol.

28. Sodium Benzoate Product will


NaOH+CaO
be

(A) (B)

25. In kolbe’s electrolytic synthesis the pOH of


solution will be
(A) decreases (B) Increases
(C) (D)
(C) Constant (D) None of these

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Page # 66 HYDROCARBON

Sol. Sol.

29. Number of required O2 mole for complete 33. e + CH3 — Cl  CH3• + Cl


combustion of one mole of propane- Above reaction is a step of wurtz reaction
(A) 7 (B) 5 electron will attack on which vacant orbital
(C) 16 (D) 10 of methyl chloride.
Sol. (A) p-orbital
(B) anti-bonding orbital
(C) s-orbital
(D) d-orbital of chlorine
Sol.

30. How much volume of air will be needed for


complete combustion of 10 lit. of ethane-
(A) 135 lit (B) 35 lit.
(C) 175 lit (D) 205 lit.
Sol.
34. Pick the correct statement for
monochlorination of R-secbutyl chlorine.
Me
Cl2
Cl H
300°C
31. BrCH2 — CH2 — CH2Br reacts with Na in the Et
presence of ether at 100°C to produce - (A) There are four possible products ; three
(A) BrCH2 — CH = CH2 are optically active one is optically inactive
(B) CH2 = C = CH2 (B) There are five possible products ; three
are optically inactive & two are optically
(C) CH 2—CH2
active
CH2 (C) There are five possible products ; two
are optically inactive & three are optically
(D) All of these
active
Sol.
(D) There are four possible products ; two
are optically active & two are optically
inactive
Sol.

O

32. H — C — O  H• + CO2
Driving force of above reaction is
(A) H = — ve, S = +ve
(B) H = – ve, S = –ve
(C) H = +ve, S = –ve
(D) H = +ve, S = +ve

394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
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HYDROCARBON Page # 67

35. Reaction :— 1 CH3—CH2—CH2—CH2—CH3 O


Cl2
Optically active monochloro product 37. A
hv Ph — C — CH3 Ph — CH2 — CH3
(s) are (R)
A could be :
CH3 (A) NH2NH2, glycol/OH–
H Cl Cl2 (B) (Zn—Hg)/conc. HCl
Reaction :— 2 (C) RedP/Hl
hv
Et
S-2-chlorobutane (D) CH2 — CH2 ; Raney Ni — H2 (mozingo)
| |
Optically active di-chloro product(s) are (S) SH SH
Sol.

Cl2
Reaction :— 3 Optically
hv
active di-chloro product(s) are (P)
Reaction :— 4 2-methoxy propane
Cl2
Optically active mono chloro
hv
product(s) are (Q)
sum of P + Q + R + S is
(A) 8 (B) 9 38. Which of the following is not produced as an
(C) 10 (D) 11 intermediate during the reation :
Sol.
Br

Na
+
Dry ether

Br

Multiple Choice Questions :



(A) CH2
NaOH
36. (X)
+
CaO
(X) will be (B) •

(A) COONa (B)


COONa (C)
COONa
(C) (D) COONa

Sol.
(D)

Sol.

394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
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Page # 68 HYDROCARBON

True or False :

41. Clemenson reduction is not useful for reduc-


tion of acid-sensitive compound
Sol.

39. Possible product during the reation will be :


Na
2EtBr 42. Wolf-kishner reduction is used for reduction
Dry ether
of Base-sensitive compound.
(A) (B) Sol.
(C) CH3 — CH3 (D)
Sol.

40. Which of the following acid salt does not give


alkene as an major product when it is
electroysed.
(A) Maleic acid (B) Oxalic acid
(C) Succinic acid (D) Adipic acid
Sol.

394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
IVRS No. 0744-2439051, 0744-2439052, 0744-2439053, www.motioniitjee.com, email-info@motioniitjee.com

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