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MUNISH KAKARs INSTITUTE OF CHEMISTRY
S.C.O. No. 203, SECOND FLOOR, SECTOR 14, PANCHKULA. Phone : 9417655033, 9888019721
ADVANCE BATCH ORGANIC
Q1. The following transformation involves a carbocation rearrangement. The carbocation isgenerated by protonation of the hydroxyl group, followed by the loss of water. Which bond
has to migrate in the carbocation to yield the product indicated (after the deprotonation) ?
OH
H
(a) (d)
(c)
(b) +
H2SO4
(a) a (b) b (c) c (d) d
Q2. Identify the major product.
OH
H2SO4 Product
(a) (b) (c) (d)
Q3. Predict the product when given compound reacts with LiAlH4:
C
H
O
O
C
OCH3
O
(A)
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MUNISH KAKARs INSTITUTE OF CHEMISTRY
S.C.O. No. 203, SECOND FLOOR, SECTOR 14, PANCHKULA. Phone : 9417655033, 9888019721
(a) O
C
OHO
O CH3
(b) OH
C
OHO
O CH3
(c) OH
HO
OH
(d)
C
OH
O
OHH
Q4. Predict the product when given compound (A, in the above question) reacts with NaBH4.
(a) O
C
OHO
O CH3
(b) OH
C
OHO
O CH3
(c) OH
HO
OH
(d)
C
OH
O
OHH
Q5.
C
O
O H
+CH3 O18
H Catalyst
HCl
C
O
O CH3
+H2O
Methyl benzoate
The labeledO18will be in :
(a) H2O (b) Methyl benzoate
(c) Both (a) and (b) (d) Benzoic acid
Q6. Which is oxidized most easily ?(a) iso - propyl alcohol (b) Ether (c) Phenol (d) 1 - Methylcyclohexan-1-ol
Q7. Which of the following react with HBr at faster rate ?
(a) OH (b) CH3
OH
(c)
OHH3C
(d)
OH
H3C
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MUNISH KAKARs INSTITUTE OF CHEMISTRY
S.C.O. No. 203, SECOND FLOOR, SECTOR 14, PANCHKULA. Phone : 9417655033, 9888019721
Q8.
OH
OH
Ph
Ph4
3
5
2
1
6 H2SO4 (P);
99% Yield
Unknown (P) of the reaction is :
(a)
C
OH
Ph
Ph4
3
5
2
1 6
(b)
C
Ph
Ph4
3
5
2
1
6
(c)
4
3
5
2
16
O
Ph
Ph
(d)
4
3
5
2
16
O
Ph
Ph
Q9. Identify the major product,
OH
O ProductH
(a) O
O
(b)O
HO
(c)O
O
(d)
O
O
Q10.
18OH
OH
4
H Br
CClMajor product obtained in the reaction is:
(a)
O
(b)
O18
(c)
Br
OH
(d)
OH
Br
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MUNISH KAKARs INSTITUTE OF CHEMISTRY
S.C.O. No. 203, SECOND FLOOR, SECTOR 14, PANCHKULA. Phone : 9417655033, 9888019721
Q11.
(b) (c) (d)
Q12. Product of the above reaction is:(a) Racemic (b) Diastereomer (c) Meso (d) Optically pure
Q13.
CH2OH
OH + Ph C
O
O H HCl
Major product of above esterification reaction is:
(b)
Q14.An organic compound B is formed by the reaction of ethylmagnesium iodide (CH 3CH2MgI)with a substance A, followed by treatment with dilute aqueous acid. Compound B doesnot react with PCC in dichloromethane. Identify A?
(a) H3C C
O
H (b) CH3CH2CCH3
O
(c) H2C=O (d) H2C
O
CH2
Q15. In which of the following group, each member gives positive iodoform test?(a) methanol, ethanol, propanone (b) ethanol, isoproponal, methanal
(c) ethanol, ethanal, isopropyl alcohol (d) propanal, propanol-2, propanone
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MUNISH KAKARs INSTITUTE OF CHEMISTRY
S.C.O. No. 203, SECOND FLOOR, SECTOR 14, PANCHKULA. Phone : 9417655033, 9888019721
Q16. Which is the best reagent to convert isopropyl alcohol to isopropyl bromide?
H3C CH
CH3
OH ?
H3C CH
CH3
Br
(a) HBr (b) SOBr2 (c) Br2 (d) CH3MgBr
Q17. NH2
OH
2100
( );o
AC O
C
A Product (A) of above reaction is:
Q18.
OH
CH3C OH
CH3 Product of the reaction is:
(a)
OH
(b)
CHO
OH
(c)
COH2
OH
(d)
O
OH
Q19.
O
H3C OH
O
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MUNISH KAKARs INSTITUTE OF CHEMISTRY
S.C.O. No. 203, SECOND FLOOR, SECTOR 14, PANCHKULA. Phone : 9417655033, 9888019721
(1) CH3MgBr/H+ (2) KMnO4(cold dill.) (3) CrO3 (4) H+/
For the above conversion the correct order of reagents used is:
(a) 1234 (b) 1432 (c) 1423 (d) 2341
Q20. Which of the following reagents would carry out the following transformation? (D = 2H)
CCH3
O
?
CCH3
OH
D
(a) NaBD4in CH3OH (b) LiAlH4, then D2O
(c) NaBD4in CH3OD (d) LiAlD4, then D2O
Q21.Identify the position where the above acetylation reaction take place.
(a) a (b) b (c) c (d) d
Q22. What is the major product of the following reaction ?
3 CrO
PyridinecoldH3C CH
OH
CH2 CH2 OHProduct
(a)
H3C C
H
OH
CH2 C
O
H
(b) H3C C
O
CH2 C
O
H
(c) H3C C
O
CH2 C
O
OH (d) H3C CH
OH
CH2 C
O
OH
Q23. 23 g of sodium will react with methyl alcohol to give:(a) one mole of oxygen (b) 22.4 dm3of hydrogen gas at NTP
(c) 1 mole of H2 (d) 11.2 L of hydrogen gas at NTP
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