Alkyl Halide: Preparation of Alkyl Halides (5-Methods)

ABC-1, 2, 3 & 4
(A) ALKYL HALIDE

Preparation of alkyl halides (5-Methods)
1. From alcohol
SOCl2
(i) from (SOCl2) in presence of pyridine CH3–CH2–OH 
CH3–CH2–Cl + SO2 + HCl
SOCl Chloroethane
R–OH 
2
 R–Cl + SO2 + HCl Ethanol Pyridine
By products
heat,pyridine are gases
It is known as Darzon method.
(ii) from PCl5 CH3–CH–OH+ PCl5 CH3–CH–Cl + HCl + POCl3
R–OH + PCl5 R–Cl + HCl + POCl3 CH3 CH3
Propan-2-ol 2-Chloropropane
(iii) from PX3 3CH3–CH2–OH +PCl3 3CH3–CH2–Cl + H3PO3
(PX PCl ,PBr ,PI )
3R–OH+PX3  3 3 3 3
 3R–X+H3PO3 Ethanol Chloroethane
(iv) Lucas test : from HX(X= Cl, Br,I) OH Cl

ZnCl2
ZnCl2 + HCl + H2O
R–OH + HX R–X + H2O
(rate : 3º ROH > 2º ROH > 1º ROH) Cyclohexanol 1-Chlorocyclohexane
h
2. Halogenation of alkane CH4 + Cl2 CH3Cl + HCl
Halogenation take place either at high Methane Chloromethane
temperature (573-773 K) or in the presence Cl
of diffuse sunlight or ultraviolet light. h
Rate of reaction of alkanes with halogens : + Cl2 + HCl
F2 > Cl2 > Br2 > I2
Cyclohexane 1-Chlorocyclohexane
3. Addition of hydrogen halides CH2 CH2 + HBr CH3CH2Br

Hydrogen halides add up to alkenes to form Ethene HCl
Bromoethane
alkyl halides. The order of reactivity of Cl

hydrogen halides is HI > HBr > HCl. CH3–C=CH2 + HCl CH3–C–CH3
CH3 CH3
2-Methylprop-1-ene 2-Chloro-2-methylpropane
4. Finkelstein reaction H H
Alkyl iodides often prepared by the reaction CH3 C CH3 + NaI Dry aceteone
CH3 C CH3 + NaCl
of alkyl chloride / bromide with Nal in dry
acetone. This reaction is known as Cl I
Finkelstein reaction. 2-Chloropropane 2-Iodopropane
Br I
dry acetone
+ NaI + NaCI
1-Bromocyclohexane 1-Iodocyclohexane
5. Swart reaction 
CH3 Cl + AgF CH3 F + AgCl
The synthesis of alkyl fluoride is best Chloromethane Fluoromethane
accomplised by heating an alkyl chloride/ Cl
bromide in the presence of a metallic fluoride
such as AgF, Hg2F2, CoF2 or SbF3. CH3 CH2 CH CH3 + AgF
The reaction is termed as Swart reaction. 2-Chlorobutane
CH3 CH2 CH CH3 + AgCl

2-Fluorobutane
F
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ABC1TO4 - 29
ABC-1, 2, 3 & 4
Chemical reactions of alkyl halide (4-Reactions)

1. Reaction of alkyl halide with H
(a) KCN CH3 CH CH3 + KCN CH3 C CH3 + KCl
KCN is predominantly ionic and
provides cyanide ions in solution. Cl CN
Although both carbon and nitrogen 2-Chloropropane 2-Methylpropanenitrile
atoms are in a position to donate Br CN
electron pairs, the attack takes place + KCN + KBr
mainly through carbon atom and not
1-Bromocyclohexane Cyclohexanecarbonitrile
through nitrogen atom since C–C bond
is more stable than C–N bond. [Only for 1º and 2º alkyl halides.]
[Phenylic, vinylic and bridge head halides fail to react by
this reaction.]
(b) AgCN CH3 Cl + AgCN CH3NC + AgCl
AgCN is mainly covalent in nature and Methylchloride Methylisocyanide
nitrogen is free to donate electron pair H
forming isocyanide as the main
product. CH3 CH CH3 + AgCN CH3 C CH3 + AgCl
Cl NC
2-Chloropropane
(c) KNO2 H
Alkyl halides (R–X) react with KNO2 to
CH3 CH CH3 + KNO2 CH3 C CH3 + KCl
give R–O–N=O (Alkylnitrite).
Cl O–N=O
Iso-propylchloride Iso-Propylnitrite
Br O N O
+ KNO2 + KBr
Cyclohexylbromide Cyclohexylnitrite
(d) AgNO2 CH3 Cl + AgNO2 CH3NO2 + AgCl

Alkyl halides (R–X) react with AgNO2 Chloromethane Nitromethane
to give R–NO2 (Nitroalkane) CH3 CH2 CH2 CH2 Cl+AgNO2
1-Clorobutane
CH3 CH2 CH2 CH2 NO2 + AgCl

1-Nitrobutane
(e) Aqueous KOH CH3 CH2 Cl + aq. KOH CH3 CH2 OH + KCl
Alkyl halides (R–X) when reacts Chloro ethane Ethanol
with aq. KOH gives alcohol H H
CH3 C CH3 + KOH(aq.) CH3 C CH3 + KCl
Cl OH
2-Chloropropane Propan-2-ol
dry ether
2. Wurtz reaction CH3 Br + 2Na + Br CH3 CH3 CH3 + 2NaBr
Alkyl halide on treatment with Bromomethane Ethane
sodium metal in dry ether solution CH3 CH3
give higher alkanes. The reaction is CH3 C Br + 2Na + Br C CH3
known as Wurtz reaction. It is used
for the preparation of higher H H
2-Bromopropane
alkanes containing even number of CH3 CH3
carbon atoms. dry ether
CH3 C C CH3 + 2NaBr
H H
2,2-Dimethyl butane
ABC1TO4 - 30
ABC-1, 2, 3 & 4
3. Wurtz-Fittig reaction Br CH3
dry ether
A mixture of an alkyl halide and aryl + 2Na + Br CH3 + 2NaBr
halide give an alkyl arene when Bromobenzene Methylbenzene
treated with sodium in dry ether. Br
Br
dry ether
+ 2Na + + 2NaBr
Bromobenzene Bromocyclohexane Cyclohexylbenzene
– +
4. Williamson ether synthesis CH3Cl + CH3O K CH3 – O – CH3 + KCl
Methyl Potassium Dimethyl
chloride methoxide ether
(B) ALCOHOL AND ETHERS

Preparation of alcohols (4-Methods)
1. From Grignard reagents [R–Mg–X] Ether H3O+
(a) CH3MgBr + HCHO CH3–CH2–OH
Grignard Reagent is an organometallic
compound. Grignard Reagent acts as base Ether H3O
+
and nucleophile. (b) PhMgBr + CH3–CHO CH3–CH–OH

(i) HCHO
R–CH2–OH (1° alcohol) Ph
(ii) H3O
CH3
(i) R–CHO Ether H3O
+
R–MgX R–CH–R (2° alcohol) (c) CH3–CH2MgBr + CH3–C–CH3 CH3–C–OH
(ii) H3O
OH O CH2CH3
O R
(i) R–C–R
(ii) H3O R–C–R (3° alcohol)
OH
2. Syn hydroxylation of alkenes (a) H2C = CH2 
4
 H2CCH2
(i) OsO
Reagents : (ii) NaHSO3

a. Baeyer's reagent: OH OH
1% alk. KMnO4
[cold dilute 1% alkaline KMnO4] or (b) CH3–CH=CH2 CH3–CH–CH2
b. (i) OsO4 (ii) NaHSO3
OH OH
Baeyer's reagent OH
(i) OsO 4
or (i)OsO4 (ii) NaHSO3 (c) 
(ii) NaHSO3
OH OH OH
Remark
It is syn addition. Both OH groups add on
the same side of pi-bond.
3. Anti hydroxylation of alkene OH
Reagent:
(i) Peroxyacid (RCOOOH) (a) +
H3O
(ii) H2O/H+ OH
OH
Peroxyacid PAA
(b) CH3–CH=CH–CH3 CH3–CH–CH–CH3
H3O+
OH OH
OH
H3O (i) Peroxy acid
C–C 

(c) (ii) H3O
OH OH
ABC1TO4 - 31
ABC-1, 2, 3 & 4
Remark
It is anti addition. Both OH groups add on
the opposite side of pi-bond.
Peroxyacid may be any one of these:
a. m-CPBA (Metachloro perbenzoic acid)
b. PAA (Peracetic acid)
c. PBA (Per benzoic acid)
d. TFPAA (Trifluoro peracetic acid).
4. Acid catalyzed hydration of alkene H
(a) CH3–CH=CH2 + H2O CH3–CH–CH3
Reagents: dil. H2SO4 or H2O/H+ or H3O+
| | OH
H2O/H
–C–C– H2O/H
| | (b) CH3–CH=CH–CH3 CH3–CH–CH–CH3
H OH H OH
Remarks: Markovnikov's addition
Preparation of ethers (2-Methods)

1. Williamson synthesis
It is an important laboratory method for (a) CH3–X + CH3–CH2–CH2O–Na CH3–O–CH2CH2CH3
the preparation of symmetrical and
unsymmetrical ethers. In this method, an (b) CH3CH2–X + PhO–Na Ph–O–CH2–CH3
alkyl halide is allowed to react with sodium
alkoxide. (c) Ph–CH2–X +Ph–CH2–O–Na PhCH2–O–CH2–Ph
– +
RX + RO–Na R–O–R + NaX
2. From alcohol
H2SO4
Alcohols undergo dehydration in the (a) CH3–CH2–OH 413 K
C2H5–O–C2H5
presence of protic acids (H2SO4, H3PO4)
H2SO4
at 413 K temperature (140ºC). (b) CH3–OH + CH3OH CH3–O–CH3
413 K
H SO
R–OH 
2 4
 R–O–R
413 K H2SO4
(c) CH3–OH + CH3–CH2–OH 413 K CH3–O–CH3
Remark :
Alcohols undergo dehydration by heating + CH3–CH2–O–CH2–CH3 + CH3–O–CH2–CH3
with conc. H2SO4 at 443K and give
alkene.
Chemical reactions of alcohols (5-Reactions)

1. Reaction with HX:
R–OH + HX R–X + H2O (a) CH3–CH2–OH HBr
CH3–CH2–Br
The reactions of primary and secondary
alcohols with HCl require a catalyst
(ZnCl2). With tertiary alcohols, the reaction HCl
conduct by simply shaking with (b) CH3–CH–OH ZnCl2
CH3–CH–Cl
concentrated HCl at room temperature. CH3 CH3
2. Reaction with phosphorus

PBr3
trihalides: (a) CH3–CH2–CH2–OH CH3–CH2–CH2–Br
3R–OH + PX3 3R–X + H3PO3
CH3
PX3 = PCl3, PBr3, PI3 | PCl3
(b) CH3 – CH2 – CH – CH2 – OH  
CH3
|
CH3 – CH2 – CH – CH2 – Cl
ABC1TO4 - 32
ABC-1, 2, 3 & 4
3. Reaction with PCl5
SN2 (a) PhCH2 OH PCl5 PhCH2Cl + POCl3
R–OH + PCl5 R–Cl + HCl + POCl3
PBr5
(b) CH3 CH OH CH3 CH Br
CH3 CH3
4. Reaction with thionyl chloride in SOCl2

presence of pyridine: (a) CH3–CH2–OH pyridine CH3–CH2–Cl
pyridine
R–OH + SOCl2 R–Cl + SO2 + HCl
SOBr2
(b) Ph–CH2–OH pyridine Ph–CH2–Br
5. Reaction with conc. H2SO4 /  (a) CH3 CH CH3

Conc. H2SO4

CH3 CH CH2
Conc. H2SO4
OH

CH3 CH3
CH3–CH=CH–CH3 (b) CH3 Conc. H2SO4
C CH3 CH3 C CH2
Remarks : 
i. Ease of dehydration of alcohol OH
    3o > 2o > 1o CH3 CH3
ii. More stable alkene (Saytzeff Alkene)
Conc. H2SO4
is formed as major product (c) CH3 CH2 C CH3 CH3 CH C CH3

OH
80ºC
CH3–CH2–OSO3H
[Alkyl hydrogen sulphate]
Conc. H2SO4 140ºC
CH3–CH2–OH CH3–CH2–O–CH2–CH3
(1º alcohol) [ether]
170ºC
CH2=CH2
[alkene]
* 2º and 3º alcohols generally give alkene at little less temperature than required for 1º alcohols.
Test of alcohols (3-Test)

S.No Test / Reagent Observation
1 Cerric ammonium nitrate test Red colour compound is formed
Reagent : [(NH4)2Ce(NO3)6]
2 Lucas reagent (a) 1° alcohol does not give appreciable reaction.
Reagent : [Conc. HCl + anhyd. ZnCl2] White turbidity is obtained on heating in 30 minutes.
Remarks : It gives white turbidity or (b) 2° alcohol gives white turbidity in 5 minutes.
cloudiness with alcohols (OH groups (c) 3° alcohol gives white turbidity immediately.
attached with sp3 hybridised carbon).
3 Victor Mayer test (a) 1° alcohol – Blood red colour.
Reagent : (i) P + I2 (b) 2° alcohol – Blue colour.
(ii) AgNO2 (c) 3° alcohol – No colour.
(iii) HNO2
(iv) Base
ABC1TO4 - 33
ABC-1, 2, 3 & 4
ONLY ONE OPTION CORRECT TYPE

PART-A (Alkyl halides)
CH2–OH
1. + PCl3 [X] + H3PO3
Product [X] is :
CH3 CH3–OH
CH2–Cl CH3
Cl
(A) (B) (C) (D)
Cl
Cl
CH3
2. CH3–C–OH + HBr [Y] + H2O
CH3
Product [Y] is :
CH3 CH3 CH3
(A) CH3–C–Br (B) CH3–C–H (C) CH3–CH2–CH2–Br (D) CH3–C–CH2–Br
CH3 CH2–Br CH3

3. [X] + PCl5 CH3–CH2–CH2–Cl + HCl + POCl3
Reactant [X] is -
CH3 CH3
(A) CH3–CH–OH (B) CH3–CH2–CH2–OH (C) CH3–CH2–CH3 (D) CH3–CH–CH3
CH2–OH
4. + PCl5 [X] + HCl + POCl3
Product [X] is :
CH2–Cl CH2–Br CH3 CH2–OH
Cl
(A) (B) (C) (D)
Cl
CH3
5. CH3–C–CH3 + Cl2 h [X] + HCl
CH3
Product [X] is -
CH3 CH3 CH3 C2H5
(A) CH3–C–CH3 (B) CH3–C–CH2 –Cl (C) CH3–CH–CH2–Cl (D) CH3–C–Cl
Cl CH3 C2H5
ABC1TO4 - 34
ABC-1, 2, 3 & 4
Cl / h
6. Iso-butane 2

No. of monochloro structural isomeric product
(A) 1 (B) 2 (C) 3 (4) 4
Cl /h
7. Iso octane 
2

(A) 7 (B) 2 (C) 3 (D) 4
Cl / h
8. Cyclopentane  2

(A) 1 (B) 2 (C) 3 (D) 4
9. CH3–CH=CH2 + HBr  [Y] ; Major product [Y] is :
CH3
(A) CH3 CH CH2 Br (B) CH3 CH2 CH2 Br

Br
H
(C) CH3 C CH3 (D) CH3 CH2 CH3

Br
Cl
10. [Z] + HCl
Reactant [Z] is :
CH3
(A) (B) (C) (D)
Dry acetone
11. CH3–CH2–Cl + NaI [X] + NaCl
Product [X] is -
(A) CH3–CH3 (B) CH3–CH2–I (C) CH3–I (D) CH3–CH2–CH2–CH3
CH2–I
12. [Z] + NaI Dry acetone
Reactant Z is :
CH2–Cl CH3 CH3 CH3
Cl
(A) (B) (C) (D)
Br
Cl
13. CH3–CH2–Cl + AgF X] + AgCl
Product [X] is -
(A) CH3–CH3 (B) CH3–CH2–F (C) CH3–CHF2 (D) CH3–F
CH2–Cl CH2–F
14. + [Y] 
Reagent [Y] can be :

(A) AgF (B) Hg2F2 (C) SbF3 (D) All
ABC1TO4 - 35
ABC-1, 2, 3 & 4
15. [Z] + CoF2 F
Reactant [Z] is :
(A) (B) (C) Cl (D)
16. CH3–CH2–CH2–Cl + KNO2 [X] + KCl

Product [X] is :
(A) CH3–CH2–CH2–O–N=O (B) CH3–CH2–CH2–NO2
(C) CH3–CH2–CH3 (D) CH3–CH=CH2
17. CH3–CH2–CH2–Cl + AgNO2 [X] + AgCl
Product [X] is :
(A) CH3–CH2–CH2–O–N=O (B) CH3–CH2–CH2–NO2
(C) CH3–CH2–CH3 (D) CH3–CH=CH2
CH3
+
18. CH3–C–O–K + CH3–Br [Y] + KBr
CH3
Product [Y] is :
CH2 CH3 CH3
(A) CH3–C–CH3 (B) CH3–C–CH2–CH3 (C) CH3–C–O–CH3 (D) CH3–CH3
CH3
CH2–Br
19. + KOH (aq.) [X] + KBr
Product [X] is :
CH3
CH2–OH CH3 CH2–Cl
(A) (B) (C) (D)
OH OH
CH3 CH3
20. In wurtz reaction, CH3–CH–CH–CH3 can be prepared from which of the following compound?
CH3
(A) CH3–C–Br (B) CH3–CH2–CH2–Br
H
CH3
(C) CH3–CH2–Br (D) CH3–C–CH2Br
CH3
21. [X] + Na Dry ether
Reactant [X] is -
Br Br
(A) (B) (C) (D)
ABC1TO4 - 36
ABC-1, 2, 3 & 4
Br
22. + C2H5Br + 2Na Dry ether [X] + 2NaBr
Major product [X] is -

C2H5
CH3
(A) (B) (C) CH3–CH2–CH2–CH3 (D) None of these
PART-B (Alcohols & Ethers)

23. Which carbonyl compound is used for following interconversion:
CH3
H3O
Carbonyl compound + CH3–CH2–MgBr + X  CH3–CH2–C–CH3
OH
(A) CH3–CHO (B) HCHO (C) CH3–C–CH3 (D) CH3–CH2–CHO
O
24. Which is correct product for given reaction?
H O
CH3–CH2–CHO + PhMgBr 
3
P
CH3
(A) CH3–CH2–CH–OH (B) CH3–C–OH
Ph Ph
CH3
(C) CH3–CH–CH2–OH (D) Ph–CH2–CH2–CH2–OH
Ph
25. Which of the following carbonyl compound will give 1° alcohol after reaction with Grignard reagent
followed by acidification:
(A) HCHO (B) CH3–CHO (C) CH3–CH2–CHO (D) CH3–C–CH2–CH3
O
26. For the following reaction:
OsO / NaHSO

4 3

 P.
Product is:
OH OH OH
(A) (B) (C) (D) OH
OH OH
27. For the following reaction:
CH3–CH=CH–CH3  CH3–CH–CH–CH3
OH OH
Reagent is :
(A) HCl (B) Dil. H2SO4 (C) Bayer's reagent (D) H2/Ni
ABC1TO4 - 37
ABC-1, 2, 3 & 4
28.
Reagent x will be :
(A) 1% alkaline KMnO4 (Baeyer’s reagent) (B) OsO4 /NaHSO3
(C) Peracid/H3O+ (D) A and B both
(i)peroxy acid
29. CH3–CH=CH–CH3 

P
(ii)H3O
Product is:
OH
(A) CH3–CH2–CH–CH2 (B) CH3–CH–CH–CH3
OH OH OH
OH
(C) CH3–CH2–CH2–CH (D) CH2–CH2–CH2–CH2
OH
OH OH
CH COOOH/ H O
30. 
3 3

 Product ; Product will be:
CH3 CH3 OH
OH CH3
(A) OH (B) (C) (D) None of these
H OH OH
OH H H
(1) Peroxyacid
31.  P ; Product is :
( 2) H3O
(A) (B) (C) (D) None of these
32. What is the final product of the following reaction?

CH –Cl
Ph–OH 
NaOH
 
3

(A) Ph–O–CH3 (B) Ph–CH3 (C) Ph–O–CH2–CH3 (D) Ph–Cl
33. In the following reaction:
C2H5ONa + C2H5Cl  product
Product is:
(A) C2H5–O–CH3 (B) C2H5–O–C2H5 (C) CH3–O–CH3 (D) C2H5–C2H5
34. Predict the suitable reagent for the following conversion:
CH3–CH2–OH  CH3–CH2–O–CH2–CH3
(A) dil. H2SO4 (B) conc. H2SO4 / 200°C
(C) conc. H2SO4 / 140°C (D) Al2O3
35. In the following reaction:
Conc.H SO
CH3–OH + CH3–CH2–OH 
2 4
product:
100–140C
Which is not a possible product?
(A) CH3–O–CH2–CH3 (B) CH3–O–CH3
(C) CH3–O–CH2–CH2–CH3 (D) CH3–CH2–O–CH2–CH3
ABC1TO4 - 38
ABC-1, 2, 3 & 4
36. Predict the reagent for the following reaction:
Ph–CH2–OH  Ph–CH2–O–CH2–Ph
(A) dil. H2SO4 (B) KMnO4 (C) LiAlH4 (D) conc. H2SO4 / 140°C
37. Which alcohol gives instant turbidity with Lucas reagent?
CH3
(A) CH3–CH2–OH (B) CH3–CH–CH3 (C) CH3–C–CH3 (D) CH3–CH2–CH2–OH
OH OH
38. Which alcohol give white turbidity in 5 minutes with Lucas reagent?
Ph
(A) CH3–CH2–OH (B) Ph–C–CH3
OH
CH3
(C) CH3–CH–CH2–CH3 (D) CH3–C–CH3
OH OH
39. Which test is used to distinguish 1°, 2°, and 3° alcohols?
(A) Victor Mayer test (B) Iodoform test
(C) NaHCO3 test (D) Bayer's test
40. Which test is not given by alcohols?
(A) Lucas Test (B) Neutral FeCl3 Test
(C) Victor major test (D) Cerric ammonium nitrate test
1. (A) 2. (A) 3. (B) 4. (A) 5. (B)
6. (B) 7. (D) 8. (A) 9. (C) 10. (C)
11. (B) 12. (A) 13. (B) 14. (D) 15. (C)
16. (A) 17. (B) 18. (C) 19. (A) 20. (A)
21. (C) 22. (B) 23. (C) 24. (A) 25. (A)
26. (B) 27. (C) 28. (D) 29. (B) 30. (B)
31. (B) 32. (A) 33. (B) 34. (C) 35. (C)
36. (D) 37. (C) 38. (C) 39. (A) 40. (B)
ABC1TO4 - 39

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ABC-1, 2, 3 & 4

(A) ALKYL HALIDE

(iv) Lucas test : from HX(X= Cl, Br,I) OH Cl

3. Addition of hydrogen halides CH2 CH2 + HBr CH3CH2Br

alkyl halides. The order of reactivity of Cl

CH3 CH2 CH CH3 + AgCl

Chemical reactions of alkyl halide (4-Reactions)

(d) AgNO2 CH3 Cl + AgNO2 CH3NO2 + AgCl

CH3 CH2 CH2 CH2 NO2 + AgCl

(B) ALCOHOL AND ETHERS

and nucleophile. (b) PhMgBr + CH3–CHO CH3–CH–OH

Reagents : (ii) NaHSO3

Preparation of ethers (2-Methods)

Chemical reactions of alcohols (5-Reactions)

2. Reaction with phosphorus

4. Reaction with thionyl chloride in SOCl2

5. Reaction with conc. H2SO4 /  (a) CH3 CH CH3

Test of alcohols (3-Test)

ONLY ONE OPTION CORRECT TYPE

1. + PCl3 [X] + H3PO3

CH3 CH2–Br CH3

4. + PCl5 [X] + HCl + POCl3

(A) CH3 CH CH2 Br (B) CH3 CH2 CH2 Br

(C) CH3 C CH3 (D) CH3 CH2 CH3

(A) (B) (C) (D)

12. [Z] + NaI Dry acetone

Reagent [Y] can be :

(A) (B) (C) Cl (D)

16. CH3–CH2–CH2–Cl + KNO2 [X] + KCl

21. [X] + Na Dry ether

(A) (B) (C) (D)

22. + C2H5Br + 2Na Dry ether [X] + 2NaBr

Major product [X] is -

PART-B (Alcohols & Ethers)

(A) (B) (C) (D) None of these

32. What is the final product of the following reaction?

1. (A) 2. (A) 3. (B) 4. (A) 5. (B)

6. (B) 7. (D) 8. (A) 9. (C) 10. (C)

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