NEXT GRAND TEST ON 27.01 - Dr. Sangeeta Khanna
Transcript of NEXT GRAND TEST ON 27.01 - Dr. Sangeeta Khanna
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1. IUPAC Naming 2. Nomenclature
3. General Organic Chemistry 4. Hydrocarbon
(Alkane, Alkene, Alkyne & Benzene) 5. Isomerism
Structural Isomerism
Conformational Isomer of Cyclohexane and
Alkane
Geometrical Isomerism (Alkene)
NEXT GRAND TEST ON 27.01.2019
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Test Dated: 23.12.2018 Topic: Organic Chemistry
READ THE INSTRUCTIONS CAREFULLY
1. The test is of 2 hour duration. 2. The maximum marks are 265. 3. This test consists of 63 questions. 4. Keep Your mobiles switched off during Test in the Halls.
Level – 1
Section – A (Single Correct Choice Type) Negative Marking
This Section contains 50 multiple choice questions. Each question has four choices A), B), C) and D) out of which ONLY ONE is correct. (Mark only One choice) 50 × 4 = 200 Marks
1. Which of the following compounds will not exhibit enolization?
a. b. c. d.
C
Sol. No - H 2. Which of the following is correct order for bond energy for C – H bonds in these compounds? a. Y > Z > X b. X > Z > Y c. X > Y > Z d. Z > X > Y C Sol. As the stability of radical increases bond energy decreases 3. Which of the following order is correct for hyperconjugation of these radicals?
a. P > Q > R b. R > Q > P c. Q > P > R d. P >R > Q D
Sol. 8 - H in P. 4. The barrier for rotation about indicated bonds will be maximum in which of these compounds?
CH2 – C – H
O
CH3 – C – CH3
O
CH3
O
CH3 H3C
H3C Ph – C – CH3
O
CH3
CH3 CH3
(P) (Q) (R)
CH2 H
X
CH2 H
Y CH2 H
Z
(X) (Y) (Z)
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a. X b. Y c. Z d. Same in all
B
Sol.
5. Consider the following reactions:
Productmajor As
SOH/HOH
NaBH )ii( Hg(OAc) )i(
2
|
|3 ]X[
product major as ]Y[
CHCH
CH
CH
CCH 42
4
2
3
3
[X] and [Y] respectively be :
a. 2, 3-Dimethyl-2-butanol and 3,3-Dimethyl-2-butanol
b. 2, 3-Dimethyl-2-butanol and 2,3-Dimethyl-2-butanol
c. 3, 3-Dimethyl-2-butanol and 3,3-Dimethyl-2-butanol
d. 3, 3-Dimethyl-2-butanol and 2,3-Dimethyl-2-butanol
A
Sol.3
|
|
|3
HOH3
||3
shif t2,13
|
|32
|
|3 CHH
CH
C
OH
CH
CCHCHH
CH
C
CH
CCHCHHC
CH
CH
CCHHCHCH
CH
CH
CCH
3333
3
3
3
3
Y is formed by Markovnikoff’s addition without rearrangement
3
||
|3
NaBH )ii(
Hg(OAc) i)(2
|
|3 CHH
OH
C
CH
CH
CCHCHCH
CH
CH
CCH
3
3
4
2
3
3
6. Consider the following reaction sequence
In this B and D respectively are a. b.
Cl2/FeCl3
HNO3/H2SO4
A HNO3/H2SO4
B
C Cl2/FeCl3
D Below 330K
[Both are aromatic]
Θ
Θ
[One ring is antiaromatic]
Θ
[One ring is antiaromatic]
Cl
NO2
and NO2
Cl Cl
NO2
and
Cl
NO2
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c. d. A Sol.
Remember : – Cl is o, p-directing while –NO2 is meta directing group. 7. Find out most stable substituted cyclohexane among the following:
a. b. c. d.
C
Sol. Bulky groups should be substituted on equatorial position. 8. Which are isomers?
a. Ethyl alcohol and dimethyl ether b. Acetone and acetaldehyde c. Propanoic acid and propanone d. Methyl alcohol and dimethyl ether A
9. Which of the following is the correct order of stability of different conformations of butane?
a. Staggered > Gauche > Partially eclipsed > Fully eclipsed b. Gauche > Staggered > Partially eclipsed > Fully eclipsed c. Staggered > Fully eclipsed > Partially eclipsed > Gauche d. None A
10. One among the following pairs of compounds is not a pair of isomers.
a. (CH3)2CHOC2H5; CH3(CH2)2OC2H5 b. CH3CH2CO2H; CH3COOCH3 c. (CH3)2CHCH2CH3; CH3CH2CH(CH3)2 d. CH3CH2NO2; CH2(NH2)COOH C
Sol. Both are same 11. Removal of a proton (H+, deprotonation) from cyclopropene is more difficult than from propene
because
a. the cyclopropenyl cation is produced b. the cyclopropenyl anion is anti-aromatic c. The allyl cation is not resonance –stabilized d. the allyl anion is not resonance-stabilized B
Cl
NO2
and
NO2
Cl NO2
Cl2/FeCl3 HNO3 Below 330K
Cl NO2
HNO3/H2SO4 Cl2/FeCl3
Cl NO2
NO2
Cl
o & p-directing (meta-directing)
o –isomer +
Cl
SO3H
and
Cl
NO2
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Sol.
12. Identify the least stable carbocation.
a. b. c. d.
D
Sol. Electron withdrawing groups decreases stability of carbocation.
13. Phenol exists in 100% enol form. The reason is
a. Phenol is more stable than its keto form as phenol is aromatic
b. Phenol has high b.p.
c. Phenol is stabilized by H-bonding.
d. Keto form is non planar
A
14. The ortho/para directing group for benzene, among the following is:
a. –COOH b. –CN c. –COCH3 d. –NHCOCH3
D
Sol. NHCOCH3 is o, p – directing while all others are m – directing.
15. The Z-isomer from the following is
(i)
5237
3
HCCCH||
HCCH
(ii)
7325
3
HCCCH||
HCCH
(iii) FCH
||BrCCl
(iv)
HCF||
BrCCl
a. only (i) b. only (iii) c. Both (i) & (iii) d. both (i) & (iv)
C
16. The type of isomerism exhibited by the compounds with formula C4H10O is/are
a. chain and position b. functional and position
c. metamerism d. chain, position, functional and metamerism
D
Sol. Alcohol & ether are functional isomer
17. The functional groups present in Cortisone are:
a. Ether, alkene, alcohol b. Alcohol, ketone, alkene, ether
c. Alcohol, ketone, ester d. Ether, amine, ketone
B
CH2 CH2
OCH3
CH2
NO2
CH3
HOH2C
O
O
OCH3
Cortisone
CH2
CH3
H H
H+ +
Θ
(Antiaromatic)
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18. The IUPAC name of the compound is : a. Toluene carbonyl chloride b. 3-Methyl benzene carbonyl chloride c. 5-Methyl benzoyl chloride d. 5-Methyl benzene carbonyl chloride B
19.
a. position isomers b. chain isomers c. functional isomers d. metamers D
20. Which of the following is not the correct order as indicated:
a. )(Stability HCCHCHHCCHHCCHCH 233322
b.
c.
d. (CH3)2CH = CH2 > CH3 – CH = CH2 > CH2 = CH2 (Stability) C
Sol. (a) = allylic free Radical is more stable than alkyl free Radical
(b) =
(c) Benzoic acid is stronger acid than alkyl carboxylic acid 21. What is the end product in the following reaction:
CBACaC3
3
AlCl
ClCH
tube glass
hot dReHOH2
a. Cyclohexane b. Benzene c. Toluene d. 2-Butene C
Sol.
22. In a mixture of Isooctane and n-heptane, the percentage of n-heptane is 60, the octane number of the
fuel is:
a. 60 b. 40 c. 20 d. 4
COCl
CH3
C O
O
and C O H
O
Θ
is aromatic and
Θ
is antiaromatic and least stable
Θ
>
Θ
>
Θ
(Stability)
>
>
(Stability)
CaC2
3
3
AlCl
ClCHHOHBenzeneCHHC
CH3
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B
Sol.Octane number is volume of Isoctane in a mixture of Isooctane & heptane, which have same knocking
as that of sample petrol
23. Which of the following acid will form Ethane on decarboxylation and butane on electrolysis of aqueous
solution of its sodium salt
a. CH3COOH b. CH3CH2COOH
c. COOHH
CH
CCH
3|
3 d. COOHH
CHCH
CCHCH
32
|23
B
Sol. CH3CH2 COOH CH3CH3
3223iselectroly s s'Kolbe
23NaOH
CHCHCHCHNaOCOCHCH
24. Which of the following on ozonolysis will form two molecule of ethanal. a. 1-Butene b. 2-Butene c. 2-Butyne d. Butane B
Sol. 33oznolysis
33 CHOCHCHOCHCHCHCHCH
25. Which is the major product (P) in the following reaction:
a. b. c. d.
B
Sol.
26. Hydroxylation of 2-butene with Baeyer’s Reagent will form a. Butan-2-ol b. Butanone c. Butane-2, 3-diol d. Butane-2,3-dione C
Sol. 3||
3agentRe
s'Baey er33 CHH
OH
CH
OH
CCHCHCHCHCH
27. Which of the following is correct order of stability of alkene?
a.
b. c.
P 1. CH3Cl, Anhyd. AlCl3
2. Oxidation 3. Cl2/FeCl3
1. CH3Cl + AlCl3
Friedal craft Reaction
CH3
Oxidation
COOH
(meta directing)
Cl2/FeCl3
COOH
Cl
CH3 – CH = CH2 < < <
CH3 – CH = CH2 < < <
< < < CH3 – CH = CH2
CH3
Cl
COOH
Cl
COOH
Cl
+
COOH
Cl
CH2Cl
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d. B
Sol. As the number of - H increases stability of alkene increases; Trans alkene is more stable than cis-alkene
28. :
Correct order of stability
a. P > Q > R > S b. P > S > Q > R c. P > R > Q > S d. S > R > Q > P C Sol. 29. In which of the following benzene ring is most electron rich.
a. b. c. d. A
Sol. 30. Bromobenzene is treated with magnesium in dry ether to form compound ‘X’ which is then treated with
ethanol to form compound ‘Y’. The compound y is
a. Benzene b. Phenol c. Ethylbenzene d. ethyl phenyl ether A
Sol. 31. Which of the following alkene has highest value of heat of hydrogenation?
a. b. c. d. D
< CH3 – CH = CH2 < <
CH2
CH3
>
CH2
CH3
(H.C & +I effect maximum)
(H.C & less +I)
>
CH2
CH3
>
CH2
(Only +I)
CH3
CH2CH3 CH
CH3 H3C
H3C – C – CH3
CH3
H C H
H
3 - H
due to maximum hyperconjugation
Br
Mg
MgBr
C2H5OH
H
+ Mg
Br
OC2H5
CH2 CH2 CH2 CH2
CH3
(Q) (R) (S)
CH3
CH3
(P)
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Sol. Compound (d) is least stable as it contain minimum no. of - H.
alkene of stability
1H ionhy drogenat
32. 2-Bromopentane COH)CH/(COK)CH( 3333 P
The major product (P) formed in the above reaction is
a. pent-1-ene b. cis pent-2-ene
c. trans pent-2-ene d. 33|
223 )CH(OCH
CH
CCHCHCH
3
A Sol. With Bulky base major product is
Hoffmann’s product is less stable alkene
3222Bulky Base
322|
3 CHCHCHCHCHCHCHCHH
Br
CCH
33. Which of the following alkene will be most stable?
a. (CH3)2CH = CH2 b. CH3CH = CHCH3 c. (CH3)2C = C(CH3)2 d. CH3CH = CH2 C
Sol. Alkene with maximum hyperconjugation is most stable. 34. Ethylbenzene with bromine in presence of FeBr3, predominantly gives
a. b. c. d. A Sol. Ethyl group is o & p-directing; In presence of FeBr3, reaction is electrophilic substitution. 35. Which alkane (molecular mass 72) would yield three different monochloro derivatives? (excluding
stereoisomer)
a. n-Pentane b. Isopentane c. neopentane d. Isohexane A
Sol. CnH2n + 2 = 72 n = 5; CH3CH2CH2CH2CH3 give three mono chloropentane 1-Chloropentane + 2-chloropentane + 3 –chloropentane & isopentane give four isomer
3|
|
33|
|
332
|
|332
|
2|
CHH
Cl
CH
CH
CCH ;CHH
Cl
CH
CH
CCH;CHCH
CH
Cl
CCH;CHCHH
CH
CH
Cl
C
3333
36. In which of the following reactions Markownikov’s rule is not observed
a. peroxide Organic
23 HClCHCHCH b. peroxide Organic
23 HBrCHCHCH
c. peroxide Organic
223 OHCHCHCH d. CH3CH = CH2 + H2SO4
B Sol. It is anti-markovnikoff’s addition is presence of peroxide. No peroxide effect with HCl, H2SO4 & H2O
CH2CH2Br Br
Br
CH2CH3 +
CH2CH3
Br
CH2CH3
Br
+
CHCH3
Br
Br
+ CH2CH2Br CH2CH3
Br
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37. In the following sequence of the reactions:
CH3CH2CH2I BA2
2
NaNH )ii(
Br )i((Alc.) KOH
The end product B is a. Alkene b. Alkanol c. Alkyne d. Alkyl amine C
Sol. )B(
3)ii(
NaNH2
||3
)i(23 CHCCHH
Br
CH
Br
CCHCHCHCHA 2
38. be can X ;XAIHCK 770
)g(Cl(alc.) KOH73
2
a. 1-chloropropene b. 3-chloropropene c. Propyl alcohol d Propene B
Sol. 22
|
onChlorinati K Ally lic 770
Cl 23
KOH .alc73 CHCHH
Cl
CCHCHCHIHC 2
39. Propene BABoil/OH)ii(
Mg/ether )I(HBr
2
In the above sequence of reactions B is
a. Propane b. Butane c. Propene d. Ethane A
Sol. 323HOH
3|
3Mg
3
|
3HBr
23 CHCHCHCHH
MgBr
CCHCHH
Br
CCHCHCHCH
40. Which one of the following will undergo meta-substitution on monochlorination?
a. Ethoxybenzene b. Chlorobenzene c. Methyl benzoate d. Phenol C
Sol. It is meta directing
41. When 3||
3 CHH
Cl
CH
Cl
CCH is treated with NaNH2 the major product formed is:
a. CH3 CH = CH2 b. CH3 – C ≡ C – CH3 c. CH2 = C = CH – CH3 d. CH2 = CH – CH = CH2
D Sol. double dehydro halogenations of dihalide will form alkyne 42. What is X in the following reaction?
a. b. c. d. A Sol.
C – O – CH3
O
CH2CHO CHO COCH3
C ≡ CH Hg
2+/HOH
H2SO4 X
O O
C ≡ CH HOH
C = CH2
OH
C – CH3
O
Hg+2
, H+
Tautomerise to Keto form
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43. Which of the following will not produce ethane?
a. Reduction of CH3COOH with HI and Red Phosphorus b. Reduction of CH3COCH3 with HI and Red Phosphorus
c. Soda lime decarboxylation of sodium propionate d. Hydrogenation of ethene in the presence of Ni B
Sol. It will produce propane
22323K 423
P red3
||
3 I2OHCHCHCHHI4CH
O
CCH
44. When CH3[CH2]3 C ≡ CH is oxidized with hot acidic KMnO4 the product is:
a. CH3CH2COOH b. CH3CH2CH2COOH c. CH3CH2CH2COOH & CO2 d. CH3CH2CH2CH2COOH & CO2 D
Sol. Alkyne give lower acid. HCOOH oxidised to give CO2.
OHCOHCOOHCOOHCHCHCHCHCHCCHCHCHCH 222223Oxidation
2223
45. A metallic carbide of gp(II) on treatment with water gives a colourless gas which burns readily in air and gives a precipitate with ammonical silver nitrate. The gas is:
a. Methane b. Ethene c. Ethyne d. Propane C
Sol. Hydrocarbon is terminal alkyne. Only terminal alkyne give white ppt. with AgNO3 & metallic carbide is CaC2.
46. Friedal craft reaction of benzene with isobutyl chloride produces:
a. isobutylbenzene b. tert–Butylbenzene c. n–butylbenzene d. sec–Butylbenzene
B
Sol. 3
|
32
|
3 CH
CH
CCHCHH
CH
CCH
33
47. YXHC3
2
42
3
FeCl
Cl
SOH
HNO66
In the above sequence Y can be a. ortho and p-Chloronitrobenzene
b. 3-Nitrochlorobenzene c. only 4-Nitrochlorobenzene d. equal mixture of all the above products B
Sol.
48. :oductPr)major(
Mole) (1 H2
H3C – C – CH3
CH3
x = NO2
; y =
NO2
Cl
; NO2 group is meta directing due to –M & –I effect
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a. b. c. d. None of these B Sol. 49. Which of the most preferred site of electrophilic attack in the following compound.
a. 2 & 3 b. 6 & 4 c. 1 & 3 d. 1, 3 & 5 B
Sol.
HN with lone pair will exert e– donating effect & makes the ring activating at o & p-position 50. An alkyl bromide (A) forms Grignard’s reagent which on treatment with water yields n-hexane . (A) with
sodium in presence of dry ether forms 4,5-diethyloctane. (A) is:
a. CH3[CH2]5Br b. CH3[CH2]3CH(Br)CH3 c. CH3 – [CH2]2 – CH(Br)CH2CH3 d. CH3[CH2]2CH(Br) CH = CH2
C Sol.
H
H
1, 4-addition product is major
NH O
1
3
2
4
5
6
CH3 – CH2 – CH2 – CH – CH2CH3
Br
Mg CH3CH2CH2 – CH – CH2 – CH3
MgBr
HOH Hexane
Na + dry ether
CH3 – CH2 – CH2 – CH – CH – CH2 – CH2 – CH3
CH2
CH3
CH2
CH3
4,5-Diethyloctane
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LEVEL – 2
SECTION – D (More than One Answer) No Negative Marking
This Section contains 5 questions. Each question has four choices A), B), C) and D) out of which ONE OR MORE may be correct. (5 × 5 = 25 Marks)
1. Which of the following represent correct matching?
a. OH
O
CCH| |
3 and 3
| |
OCH
O
CH Metamers
b. CH3 – CH2 – C CH and CH3 – C C – CH3 Position isomers
c. CH3CH2CH2NH2 and 3
2
|3 CHH
NH
CCH Tautomers
d. CH3CH2OH and (CH3)2O Functional isomers. B,D
Sol. Metamers have same functional group. 2. Which of the following cycloalkanes will show cis-trans isomerism?
a. b. c. d. C,D 3. Keto-enol tautomerism is observed in:
(a) C6H5 – CHO (b) C6H5COCH3 (c) C6H5COC6H5 (d) C6H5COCH2COCH3 B,D
4. Which of the following alkenes are more stable than ? a. b. c. d. A,B,C,D Sol. A = 10 CH; B = 5 – CH; C = 4CH; D = 4 – CH; given compound have – 3CH 5. Which of the following compound on oxidation with acidic KMnO4 will give Benzoic acid?
a. Ethylbenzene b. Benzaldehyde c. Phenol d. Methylbenzene A,B,D
Sol.
CH3
CH3
CH3
CH3
H3C
CH3 H3C
CH2CH3 COOH CH2OH
CH3
CHO
Toluene
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SECTION – E (Matrix Type) No Negative Marking
This Section contains 2 questions. Each question has four choices (A, B, C and D) given in Column I and five statements (p, q, r, and s) in Column II. (2 × 8 = 16 Marks)
1. Match the Column – I with Column – II. (More than one Match)
Column- I Column – II a. (p) Structural isomer b. (q) Functional isomers
c. (r) Tautomerism
d. CH3 – CH2COOH & H
O
CCHH
OH
C||
22|
(s) Metamerism
Sol. A p,q,r; B p,q,r; C s,p; D p,q 2. Match Column (I) with Column (II). (More than One Match)
Column – I Column – II
(a) (p) Nucleophilic substitution
(b) (q) Electrophilic substitution
(c) (r) Cation intermediate
(d) (s) Free radical substitution Sol. A – (q), (r); B – (q), (r) ; C – (p); D – (s)
(a) In electrophilic substitution, Intermediate is cation.l
Et
Me
Et
N and
Me
Pr
N Me
CHO and
OH
NH HN
O
N O O
H
and
OH
N
HO OH
N
N
+ Ph – CH2 – Cl AlCl3
CH2 – Ph
H3C – C – CH3
CH3
CH3
Br2, hv CH3 – C – CH2 – Br
CH3
CH3
+ HNO3 H2SO4 NO2
Br
KCN CH3 – CH – CH3
CN
+ KBr
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SECTION – F (Integer Type) No Negative Marking This Section contains 6 Questions. The answer to each question is a Single Digit Integer ranging
from 0 to 10. 6 × 4 = 24 Marks
1. The number of geometrical isomers in case of CH3 – CH = CH – CH = CH – C2H5 is Sol. 2n = 4 2. Examine the structural formulas of following compounds and find how many compounds will produce
CO2 on with hot acidic KMnO4
(a) , (b) , (c) , (d)
(e) , (f) H3C – C CH, (g) Ph – CH = CH2 Sol. 5 (b); (c); (e); (f); (g) (terminal alkene & alkyne) 3. From the following compounds/ ions:
(a) 3HC
(b) 4HN
(c) BF3 (d) NH3 (e) AlCl3 (f) F– (g) 2CCl (h) CH2 = CH2
Identify value of X. Where X is the total number of electrophiles. Sol.4 (a, c, g, e) 4. How many trichloroethanes would be produced when 1,1-Dichloroethane reacts with chlorine? Sol. 2;
5. How many of the following are meta directing and deactivating than Benzene Sol. 4; (ii), (iii), (iv), (viii) 6. The total number of structural isomers possible for structure C3H6 are Sol. 2
C – C = C &
CH3 – C – Cl
Cl
Cl
& CH2 – CH Cl
Cl
Cl2 h
CH3 – CH Cl
Cl
Cl
(i)
Cl
; (ii)
NO2
; (iii)
CN
; (iv)
COOH
;
(v)
O – C – CH3
;
O
NH2
; (vi)
C(CH3)3
; (vii)
CF3
(viii)