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1: When isobutane is monochlorinated in the presence of ultraviolet light, the product obtained in
higher yield is
(a) n-butyl chloride (b) iso butyl chloride
(c) sec-butyl chloride (d) tert-butyl chloride
Solution:
=

=
% of isobutyl chloride =
% of tertbutyl chloride=
The answer is (b)
2: The product of reaction CH
3
CH
2
CH
2
MgBr + HCCCH
3

is
(a) CH
3
CH
2
CH
3
(b) CH
3
CH
2
CH
2
C C CH
3

(c) CH
3
CH
2
CH
2
OH (d) CH
3
CH
2
CHO
Solution: Grignard reagent reacts with any compound having active hydrogen producing an alkane.
nC
3
H
7
MgBr + HC CCH
3
nC
3
H
8
+ CH
3
C CMgBr
The answer is (a)

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3:
The major product (A) in above given reaction is:
(a) (b)
(c) (d)
Solution: The reaction proceeds as follows:

Markovnikov's rule is not applicable because of carbocation rearrangement.
The answer is (c)

4: 1-butyne can be distinguished from 2-butyne by using
(a) bromine water (Br
2
in CCl
4
)
(b) coldalk. KMnO
4
(Baeyer's Reagent)
(c) ammoniacal solution of silver (Tollen's Reagent)
(d) diethyl ether
Solution: Terminal alkynes form a precipitate with Tollen's reagent.
RC CH + Ag
+
RC C
_
: Ag
+
+ H
2

ppt. of Silver acetylide
1-butyne, a terminal alkyne gives this reaction but
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2-butyne, a non-terminal alkyne does not give this reaction.
The answer is (c)
5: The ozonolysis of a triple bond produces
(a) a mixture of aldehydes and ketones
(b) a mixture of ketones and carboxylic acids
(c) a mixture of carboxylic acids
(d) none of the above
Solution:
The answer is (c)

6: One of isomers (A) of 2-butene gives a racemic mixture on addition of Br
2
whereas another isomer
(B) gives a meso compound on addition of Br
2
. (A) and (B) are respectively:
(a) cis and trans-2-butene (b) trans and cis-2-butene
(c) both are cis (d) none of the above
Solution: Cis isomer on anti-addition gives a racemic mixture and a meso compound on syn-addition but
a trans isomer gives a meso compound on anti-addition and a racemic mixture on syn addition. Br
2
also
adds in anti manner.
The answer is (a)
7: An alkene with the lowest heat of hydrogenation is
(a) CH
3
CH = CH CH
3
(b)
(c) (d)
Solution: The more substituted an alkene the more stable it is and lower its heat of hydrogenation.
The answer is (b)
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8: Which of the following halides does not form precipitate with alcoholic silver nitrate?
(a) ethyl chloride (b) 3-chloropropene
(c) chlorobenzene (d) isobutyl chloride
Solution: Only aryl and vinyl halides are incapable of forming silver halide precipitates with alc.
AgNO
3
.
The answer is (c)
9:
The major product is
(a) (b)
(c) (d)
Solution: The conjugation of double bond with an aromatic ring yields a highly stable system.
Unusually stable
Hence, (a) being highly stable is the major product.
The answer is (a)
10: Which of the following aryl halides undergoes hydrolysis most readily with aq. NaOH.
(a) (b)
(c) (d)
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Solution: The greater the number of electron withdrawing groups at ortho/para positions to halogen,
the greater the reactivity of aryl halides towards nucleophilic substitution.

11: gives as the major product on hydrolysis. The yield of
the product will be maximum when
(a) water is solvent and X = I (b) dimethyl sulfoxide is solvent and X = I
(c) water is solvent and X = Br (d) water is solvent and X = Cl.
Solution: The mechanism of reaction must be S
N
2, because if it was S
N
1 the carbo-cation
rearrangement would yield (CH
3
)
3
COH as the major product. S
N
2reaction is assisted by an aprotic
solvent-like dimethyl sulfoxide and a good leaving group like iodide.
The answer is (b)
12: Hydrolysis by S
N
2 mechanism will be shown by
(a) C
6
H
5
CH
2
Br (b) CH
3
Br
(c) CH
2
= CH CH
2
Br (d) (CH
3
)
3
C Br

Solution: (a), (c), and (d) can form highly stable carbo-cations and thus show S
N
1 mechanism. CH
3
Br
is a (1) halide and has a greater tendency towards S
N
2 reaction.
The answer is (b)
13:
(D) is
(a) 1,2,3-tribromo-3-
methyl butane (b) 1,2,3-
tribromo-2-methyl
butane
(c) 1,1,3-tribromopentane
(d) 1,3,3-tribromo-3-methyl butane


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Solution:
The answer is (a)

14: What is the order of reactivity of the following compounds towards aq. NaOH?

(a) IV > II > III > I (b) III > II > I > IV
(c) I > II > III > IV (d) IV > I > III > II
Solution: (IV) is an alkyl halide and undergoes substitution fastest through S
N
2 mechanism.
(I), (II), and (III) are aryl halides and undergo substitution through bimolecular displacement
reaction where reactivity is increased by electron-withdrawing groups ortho/para to halogen and
decreased by electron-releasing groups.
The answer is (a)
15: A hydrocarbon (A) (molecular formula C
6
H
12
) decolorises Br
2
in CCl
4
and is oxidised by hot
acidified KMnO
4
to a resolvable carboxylic acid, C
4
H
9
COOH.
Determine (A).
Solution: Since the carboxylic acid, C
4
H
9
COOH is resolvable (optically active) it must have a chiral
centre and only structure of the acid that is optically acive is
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And, the alkene which on oxidation with hot acidified KMnO
4
gives the acid is

Hence, (A) is 3-methyl pentene
16: (a) Outline synthesis of propyne from isopropyl bromide.
(b) One mole of a hydrocarbon (A) reacts with one mole of bromine giving a dibromo compound
C
5
H
10
Br
2
. (A) on treatment with cold alkaline KMnO
4
forms compound of molecular formula
C
5
H
12
O
2
. On ozonolysis, (A) gives equimolar quantities of propanone and ethanal. Deduce the
structural formula of (A).
Solution: (a)

(b) Hydrocarbon (A) must be an alkene because
(i) it shows addition reaction
(ii) undergoesozonolysis reaction giving propanone and ethanal
Hence, (A) should be


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17: An alkane (A), C
5
H
12
on chlorination at 300C gives a mixture of four different monochlorinated
derivatives (B), (C), (D), and (E). Two of these derivatives give the same stable alkene (F) on
dehydrohalogenation. On oxidation with hot alkaline KMnO
4
followed by acidification, (F) gives two
products (G) and (H). Give structures of (A) to (H).
Solution: The only alkane of molecular formula C
5
H
12
that gives four monochlorinated isomers is

Out of these, (C) and (D) give the same alkene on dehydrohalogenation.

On oxidation with hot alkaline, KMnO
4
(F) gives

18: Calculate the percentages of various isomers formed during mono-chlorination of 2,3-dimethyl
pentane at room temperature. The relative reactivity orders of 3, 2, 1 H atoms are 5 : 3.8 : 1.
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Solution :


Relative proportions:
A : B : C : D : E : F
= 6 1 : 1 5 : 1 5 : 3 1 : 2 3.8 : 3 1
= 6 : 5 : 5 : 3 : 7.6 : 3
% of :
A = = 20.27%
C, B = = 16.89% each
F, D = = 10.13% each
E = = 25.67%
19: An alkyl halide C
6
H
13
Cl (A) on treatment with tertiary butoxide gives two isomeric alkene B (as
major product) and C (as minor product). B and C have molecular formula C
6
H
12
and both on
hydrogenation give 2,3-dimethyl butane. What are A, B and C?
Solution: Two alkene which on hydrogenation give 2,3-dimethyl butane are

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For (A) to give these alkenes on dehydrohalogenation, its structure should be

Because of bulky base being used here less substituted alkene is the major product.
Hence, (B) is [2, 3-dimethyl but-1-ene]
And, (C) is [2,3-dimethyl but-2-ene]
20: Two isomeric organic compounds (A) and (B) of molecular formula C
4
H
8
Br
2
on hydrolysis gave
two compounds (C) and (D) of formula C
4
H
8
O. (C) and (D) gave two isomeric acids (E) and (F) of
formula C
4
H
8
O
2
on oxidation. Both the acids on decarboxylation with
soda-lime gave propane. Identify (A) to (F).
Solution: There are only two carboxylic acids having formula C
4
H
8
O
2
. They are
and (F)
on decarboxylation both give propane.



21: An organic compound (A) having molecular formula C
7
H
15
Cl yields a white precipitate when
treated with AgNO
3
. On treatment with alcoholic potash, (A) yields a mixture of two isomeric
products (B) and (C) having formula C
7
H
14
. The ozonolysis of this mixture yielded four compounds.
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, , HCHO and .
Identify (A), (B), and (C).
Solution: (B) and (C) must be alkenes containing seven carbon atoms each. (Since alkyl halide from
which they are formed contains seven C atoms).
Hence, and O = CH
2
must be ozonolysis products of one of alkenes (B) and
and must be obtained from (C).
[\ the number of C atoms adds upto 7]
Hence, (B) and (C) are
+ HCHO

(B) and (C) can be obtained by dehydrohalogenation as :

22: An unsaturated hydrocarbon (A) (C
6
H
10
) readily gives (B) on treatment with NaNH
2
in liquid
NH
3
. When (B) reacts with 1-chloropropane the compound (C) is obtained. On partial hydrogenation
with Lindlar's catalyst (C) gives (D) (formula = C
9
H
18
). On ozonolysis, (D) gives 2,2-dimethylpropanal
and 1-butanal. Identify (A), (B), (C) and (D).
Solution: (A) should be an alkyne as indicated by molecular formula C
6
H
10
and since it reacts with
NaNH
2
in liquid NH
3
(A) should be a terminal alkyne.
Hence, (A) should be of type RC CH

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The products of ozonolysis are given as
and
Hence, R is tert-butyl group. R =
Hence, (A) : (CH
3
)
3
CC CH 3, 3-dimethyl but-1-yne
(B) : (CH
3
)
3
CC C
_
Na
+

(C) : (CH
3
)
3
CC CCH
2
CH
2
CH
3
2,2-dimethyl hept-3-yne
(D) : Cis-2,2-dimethyl hept-3-ene


23: A dihalogen derivative (A) of a hydrocarbon having two carbon atoms reacts with alcoholic potash
and forms another hydrocarbon which gives a red precipitate with ammonical cuprous chloride.
Compound `A' gives an aldehyde when treated with aqueous KOH. Determine (A).
Solution: (A) can be or CH
3
CH Cl
2

Both can react with alcoholic potash forming ethyne.
But only CH
3
CH Cl
2
can form aldehyde with aqueous KOH.
Hence, (A) = CH
3
CHCl
2


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24 24 24 24. .. . Explain which of the following ieactions woulu pioviue a bettei synthesis of Explain which of the following ieactions woulu pioviue a bettei synthesis of Explain which of the following ieactions woulu pioviue a bettei synthesis of Explain which of the following ieactions woulu pioviue a bettei synthesis of
2 2 2 2 - -- - pentene. pentene. pentene. pentene.
(i) (i) (i) (i)

C H
3
Br
CH
3
CH
3
O
CH
3
OH

(ii) (ii) (ii) (ii)
C H
3
CH
3
Br
CH
3
O
CH
3
OH


Solution: Solution: Solution: Solution: (i) (i) (i) (i)

C H
3
Br
CH
3
C H
3
CH
3
Only product

(ii) (ii) (ii) (ii)
C H
3
CH
3
Br
C H
3
CH
2
C H
3
CH
3
Mixture

Bence (a) is bettei Bence (a) is bettei Bence (a) is bettei Bence (a) is bettei

2S 2S 2S 2S. C . C . C . CS SS SB BB B1u 1u 1u 1u iepiesents thiee isomeiic alkenes A iepiesents thiee isomeiic alkenes A iepiesents thiee isomeiic alkenes A iepiesents thiee isomeiic alkenes A1 11 1, A , A , A , A2 22 2 anu A anu A anu A anu AS SS S. Each on hyuiogentation gives 2 . Each on hyuiogentation gives 2 . Each on hyuiogentation gives 2 . Each on hyuiogentation gives 2 - -- - methyl methyl methyl methyl
butane. A butane. A butane. A butane. A1 11 1 anu A anu A anu A anu A2 22 2 on oxymeicuiation on oxymeicuiation on oxymeicuiation on oxymeicuiation - -- - uemeicuiation gives the same S uemeicuiation gives the same S uemeicuiation gives the same S uemeicuiation gives the same S
u uu u
alcohol. A alcohol. A alcohol. A alcohol. A2 22 2 anu anu anu anu
A AA AS SS S on hyuioboiation oxiuation gives uiffeient 1 on hyuioboiation oxiuation gives uiffeient 1 on hyuioboiation oxiuation gives uiffeient 1 on hyuioboiation oxiuation gives uiffeient 1
u uu u
alcohol. Assign stiuctuies to A alcohol. Assign stiuctuies to A alcohol. Assign stiuctuies to A alcohol. Assign stiuctuies to A1 11 1, A , A , A , A2 22 2 anu anu anu anu
A AA AS SS S anu explain the ieactions. anu explain the ieactions. anu explain the ieactions. anu explain the ieactions.
Solution: Solution: Solution: Solution:

A
1
, A
2
or A
3

H
2
C H
3
CHCH
2
CH
3
CH
3

This shows that each of A This shows that each of A This shows that each of A This shows that each of A1 11 1, A , A , A , A2 22 2 anu A anu A anu A anu AS SS S have same C have same C have same C have same C - -- - chain only position of chain only position of chain only position of chain only position of
C = C is to be ueciueu C = C is to be ueciueu C = C is to be ueciueu C = C is to be ueciueu

oxymercuration 0
1 2
demerocuration
A , A 3 Alcohol
hence A hence A hence A hence A1 11 1 anu A anu A anu A anu A2 22 2 have have have have


C
CH
3
CH
3

oi oi oi oi
H
2
C C CH
3
CH
3
giouping giouping giouping giouping

hydroboration oxidation 0
1 3
A and A 1 Alcohol
This inuicates piesence of (CB This inuicates piesence of (CB This inuicates piesence of (CB This inuicates piesence of (CB2 22 2 =) giouping at the teiminal. Bence =) giouping at the teiminal. Bence =) giouping at the teiminal. Bence =) giouping at the teiminal. Bence


CH
3
C CHCH
3
CH
3
A
1
is

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CH
3
CH
2
C CH
2
CH
3
A
2
is


A
3
is
CH
3
HC
CH
3
CH CH
2


A
1
or A
2

oxymercuration
demercuration
C H
3
C CH
2
CH
3
OH
CH
3
3
0
alcohol (X)


A
2

hydroboration
oxidation

1
0
alcohol (Y)
CH
3
CH
2
CHCH
2
OH
CH
3


A
3

hydroboration
oxidation

1
0
alcohol (Z)
CH
3CHCH
2
CH
2
OH
CH
3

Y anu Z aie uiffeient 1 Y anu Z aie uiffeient 1 Y anu Z aie uiffeient 1 Y anu Z aie uiffeient 1
u uu u
alcohols alcohols alcohols alcohols
26 26 26 26. .. . An olefin was tieateu with ozone anu the iesulting piouuct on ieuuction (ieuuctive An olefin was tieateu with ozone anu the iesulting piouuct on ieuuction (ieuuctive An olefin was tieateu with ozone anu the iesulting piouuct on ieuuction (ieuuctive An olefin was tieateu with ozone anu the iesulting piouuct on ieuuction (ieuuctive
ozonolysis) gave 2 ozonolysis) gave 2 ozonolysis) gave 2 ozonolysis) gave 2 - -- - pentanone anu acetaluehyue. What is the stiuctuie of olefin. Wiite pentanone anu acetaluehyue. What is the stiuctuie of olefin. Wiite pentanone anu acetaluehyue. What is the stiuctuie of olefin. Wiite pentanone anu acetaluehyue. What is the stiuctuie of olefin. Wiite
the ieaction. the ieaction. the ieaction. the ieaction.
Solution: Solution: Solution: Solution:
Alkene is C C
CH
2
CH
2
CH
3
CH
3
C H
3
H
(z) - 3 - methyl hex - 2 - ene
H
3
C CH
2
CH
2
C CH
CH
3
C H
3
3
O

O
CH
O
C
O
CH
3
C H
3
H
3
CH
2
CH
2
C
H
2
O / Zn
H
3
CH
2
CH
2
C
C O
C H
3
O CH
CH
3



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27 27 27 27. .. . 2 22 2- -- -Butyne unueigoes following ieactions in steps as inuicateu. Iuentify A to B. Butyne unueigoes following ieactions in steps as inuicateu. Iuentify A to B. Butyne unueigoes following ieactions in steps as inuicateu. Iuentify A to B. Butyne unueigoes following ieactions in steps as inuicateu. Iuentify A to B.

CH
3
C CCH
3
H
2
Ni
2
B
A
D
2
/Pt
B
C
Na/EtOH D
2
/Pt
D
E
Br
2
F
G
H
2
Ni
H
H
2
Ni
2
B
Br
2

Solution: Solution: Solution: Solution: A is obtaineu by syn auuition A is obtaineu by syn auuition A is obtaineu by syn auuition A is obtaineu by syn auuition

C C
C H
3
H H
CH
3
A :
Cis

B is also obtaineu by syn auuition B is also obtaineu by syn auuition B is also obtaineu by syn auuition B is also obtaineu by syn auuition

B :
C H
3
C C CH
3
H H
D D
meso

C is obtaineu by anti auuition C is obtaineu by anti auuition C is obtaineu by anti auuition C is obtaineu by anti auuition

C C
H
C H
3
H
CH
3
C :
Cis

B is mixtuie of u B is mixtuie of u B is mixtuie of u B is mixtuie of u - -- - anu anu anu anu - -- - (iacemic mixtuie) (iacemic mixtuie) (iacemic mixtuie) (iacemic mixtuie)

D :
C H
3
C C CH
3
D H
D H



u u u u - -- - anu anu anu anu - -- - (iacemic) (iacemic) (iacemic) (iacemic)

E is obtaineu by syn auuition E is obtaineu by syn auuition E is obtaineu by syn auuition E is obtaineu by syn auuition
E : as A E : as A E : as A E : as A
Auuition of Bi Auuition of Bi Auuition of Bi Auuition of Bi2 22 2 is anti is anti is anti is anti

F :
C H
3
C C CH
3
Br H
Br H
racemic

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G : C C
C H
3
Br CH
3
Br
trans
H : as F







28 28 28 28. .. .

nBuC CMe
Li, NH
3
A
KMnO
4
B
HCO
3
H
H
2
Lindlar's catalyst
C

Place each of the following alkanes in oiuei of coiiesponuing incieasing boiling point (bp Place each of the following alkanes in oiuei of coiiesponuing incieasing boiling point (bp Place each of the following alkanes in oiuei of coiiesponuing incieasing boiling point (bp Place each of the following alkanes in oiuei of coiiesponuing incieasing boiling point (bp C) anu give C) anu give C) anu give C) anu give
youi ieason foi the oiuei: pentane, hexane anu 2, S youi ieason foi the oiuei: pentane, hexane anu 2, S youi ieason foi the oiuei: pentane, hexane anu 2, S youi ieason foi the oiuei: pentane, hexane anu 2, S - -- - uimethyl butane. uimethyl butane. uimethyl butane. uimethyl butane.
Sol. Sol. Sol. Sol. C CC CS SS SB BB B12 12 12 12 with a lowei moleculai weight, has a lowei boiling point than both C with a lowei moleculai weight, has a lowei boiling point than both C with a lowei moleculai weight, has a lowei boiling point than both C with a lowei moleculai weight, has a lowei boiling point than both C6 66 6B BB B14 14 14 14isomeis. The isomeis. The isomeis. The isomeis. The
biancheu 2, S biancheu 2, S biancheu 2, S biancheu 2, S - -- - uimethyl butane has a lowei boiling point than the stiaight chain isomei uimethyl butane has a lowei boiling point than the stiaight chain isomei uimethyl butane has a lowei boiling point than the stiaight chain isomei uimethyl butane has a lowei boiling point than the stiaight chain isomei
because it is a moie compact molecule with less suiface aiea anu thus has weakei because it is a moie compact molecule with less suiface aiea anu thus has weakei because it is a moie compact molecule with less suiface aiea anu thus has weakei because it is a moie compact molecule with less suiface aiea anu thus has weakei
inteimoleculai van uei Waal's attiactive foices. The actual boiling points aie S6 inteimoleculai van uei Waal's attiactive foices. The actual boiling points aie S6 inteimoleculai van uei Waal's attiactive foices. The actual boiling points aie S6 inteimoleculai van uei Waal's attiactive foices. The actual boiling points aie S6

C foi pentane, C foi pentane, C foi pentane, C foi pentane,
S8 S8 S8 S8 C foi 2, S C foi 2, S C foi 2, S C foi 2, S - -- - uimethyl butane anu 69 uimethyl butane anu 69 uimethyl butane anu 69 uimethyl butane anu 69 C foi hexane. C foi hexane. C foi hexane. C foi hexane.
29 29 29 29. List foui chemical tests to uistinguish an alkene fiom an alkane. . List foui chemical tests to uistinguish an alkene fiom an alkane. . List foui chemical tests to uistinguish an alkene fiom an alkane. . List foui chemical tests to uistinguish an alkene fiom an alkane.

Sol. Sol. Sol. Sol. A positive test is inuicate A positive test is inuicate A positive test is inuicate A positive test is inuicateu by one oi moie uetectable events such as a coloui change, u by one oi moie uetectable events such as a coloui change, u by one oi moie uetectable events such as a coloui change, u by one oi moie uetectable events such as a coloui change,
appeaiance of an insoluble soliu oi liquiu, evolution of a gas, uptake of a gas, oi evolution of appeaiance of an insoluble soliu oi liquiu, evolution of a gas, uptake of a gas, oi evolution of appeaiance of an insoluble soliu oi liquiu, evolution of a gas, uptake of a gas, oi evolution of appeaiance of an insoluble soliu oi liquiu, evolution of a gas, uptake of a gas, oi evolution of
heat. heat. heat. heat.

C C
Br
2
(red)
CCl
4
C C
Br Br
(colourless)
(loss of colour)


C C
KMnO
4
C C
OH OH
(colourless)
( MnO
2
)
(purple)
brown-black precipitate)
(loss of colour and formation of ppts)



C C
H
2
SO
4
(conc.)
C C
H
(Solubility in sulphuric acid)
HSO
4 Heat

Answei Sheet Answei Sheet Answei Sheet Answei Sheet Page Page Page Page 17 17 17 17
EB0BIuN EB0BIuN EB0BIuN EB0BIuN 46C Chowiinghee Roau, Kolkata 71 www.euuuigm.in Su8116u8

C C
H
2
C C
H H
(uptake of a gas)
Pt

Alkanes give none of these tests. Alkanes give none of these tests. Alkanes give none of these tests. Alkanes give none of these tests.
Su Su Su Su. uive the equations foi the ieactions of piopyne with . uive the equations foi the ieactions of piopyne with . uive the equations foi the ieactions of piopyne with . uive the equations foi the ieactions of piopyne with
(i) Na (in hexane) (i) Na (in hexane) (i) Na (in hexane) (i) Na (in hexane)
(ii) Na (ii) Na (ii) Na (ii) Na
+ ++ +
NB NB NB NB2 22 2

(in liquiu NB (in liquiu NB (in liquiu NB (in liquiu NBS SS S) ) ) )
(iii) Ag(NB (iii) Ag(NB (iii) Ag(NB (iii) Ag(NBS SS S) )) )2 22 2
+ ++ +
0B 0B 0B 0B


(iv) Cu(NB (iv) Cu(NB (iv) Cu(NB (iv) Cu(NBS SS S) )) )2 22 2
+ ++ +
0B 0B 0B 0B


Also state the chemical piopeity of piopyne uue to which these ieactions take place. Also state the chemical piopeity of piopyne uue to which these ieactions take place. Also state the chemical piopeity of piopyne uue to which these ieactions take place. Also state the chemical piopeity of piopyne uue to which these ieactions take place.
(i) (i) (i) (i)
( )
3 3 2
an alkynide anion sodium propynide
2CH C CH 2Na 2 CH C C : Na H
+
+ +


(ii) (ii) (ii) (ii)
3
liq. NH
3 2 3 3
CH C CH NaNH CH C C: Na NH
+
+ +
(iii) (iii) (iii) (iii) ( ) ( )
3 3 3 3 2
2
CH C CH Ag NH OH CH C CAg s 2NH H O
+

+ + +
(iv) (iv) (iv) (iv) ( ) ( )
3 3 3 3 2
2
CH C CH Cu NH OH CH C CCu s 2NH H O
+

+ + +
The aciuity of the teiminal B of a teiminal alkyne is iesponsible foi these ieactions. The aciuity of the teiminal B of a teiminal alkyne is iesponsible foi these ieactions. The aciuity of the teiminal B of a teiminal alkyne is iesponsible foi these ieactions. The aciuity of the teiminal B of a teiminal alkyne is iesponsible foi these ieactions.
S1 S1 S1 S1. .. . uive the mechanism of the following conveision: uive the mechanism of the following conveision: uive the mechanism of the following conveision: uive the mechanism of the following conveision:

CH
2
OH

Sol. Sol. Sol. Sol. CH
2
OH
H
+

CH
2
OH
2
-H
2
O
CH
3
ring
expansion

H
+

S2 S2 S2 S2. .. . Complete the following ieactions: Complete the following ieactions: Complete the following ieactions: Complete the following ieactions:
(i) (i) (i) (i)
OH

ERROR: rangecheck
OFFENDING COMMAND: .buildcmap
STACK:
-dictionary-
/WinCharSetFFFF-V2TT9BF4ACCAt
/CMap
-dictionary-
/WinCharSetFFFF-V2TT9BF4ACCAt