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30 have one or more than one correct alternative(s) and carry 3 marks each. There is NEGATIVE marking and 1 mark will be deducted for each wrong answer. 1. A compound with molecular formula C6 H14O 4 does not give litmus test and does not give colour with 2, 4DNP. It reacts with excess MeCOCl to give a compound whose vapour density is 117. Compound A contains how many hydroxy groups? (A) 1 (B) 2 (C) 3 (D) 4 2. When isopentane is subjected to monochlorination. What will be the number of monochlorinated product contain chiral carbon? (A) 2 (B) 3 (C) 4 (D) 5 3. The heat of hydrogenation of 1-hexene is 126 kJ mol. When a second double bond is introduced in the molecule, the heat of hydrogenation of the resulting compound is found to be 230kJmol1 . The resulting compound (diene) is (A) 1: 5 hexadiane (B) 1: 4 hexadiene (C) 1: 3 hexadiene (D) cannot predict from the given information Cl2 Br2 CH 3CH 2CH 3 A B 4. hv hv A and B are: Br
Cl
Time: 50 Min.
Br Cl
(A) CH3CH 2CH 2Cl and CH3CH CH 2 Cl (B) CH3CHCH3 and CH3 CHCH 2 Cl Cl Cl Cl (C) CH3CHCH 3 and CH 3CH CH 2 Br 5. (D) CH3CHCH3 and CH3 C CH 3
Br Which one of the following compounds gives acetone ( CH3 ) 2 C = O as one of the products of its ozonolysis? (C)
Br2 Pr oduct CCl 4
(A) (B) 6.
(D)
CH 3 Product obtained in the above reaction is (A) Diastereomers (C) Meso compound 7. Monomer used to prepare Orlon is: (A) CH 2 = CHCN (B) CH 2 = CH Cl NH 2 8.
conc.H 2SO 4 Br2 H 2 O ( X ) ( Y ) excess Product (Y) of above reaction is
(B) Enantiomer (D) Single pure enantiomer (C) CH 2 = CHF (D) CH 2 = CCl2
NH 2 Br SO3 H
5
NH 2 Br Br
Br
SO3H
(A)
(B)
NH 2
Br Br
NH 2 Br (D) Br SO3H Br
(C)
Br
OC2 H5
O
9.
+ is OC2 H5
[ Z]
OC2 H 5 O (B)
(D) none
10.
N N
K (IV)
(B) I and II
(C) II and IV
11.
OH
CH = CH CH 3
CH = CH CH 2 OH CH 3
(C)
OH
(D)
12.
CH 2
CHO
14
14
CHO
Zn Hg A HCl
Final major product of this reaction is (A) CH 3 CH 2 CH3 (C) CH 3 CH 2 CHO 13.
14
14
Compound A (molecular formula C3H8O ) is treated with acidified potassium dichromate to form a product B (molecular formula C3H 6 O ). B forms a shining silver mirror on warming with ammoniacal silver nitrate, B when treated with an aqueous solution of NH 2 NHCONH 2 and sodium acetae give a product C. Identify the structure of C. (A) CH 3CH 2CH = NNHCONH 2 (B) CH 3C = NHHCONH 2 CH 3 (C) CH 3C = NCONHNH 2 CH 3 (D) CH3CH 2CH = NCONHNH 2
14.
Compound D of the above reaction is Bu (A) (B) COOH 15. (A) Iodoform 16.
O
Bu COPh
Bu (D) C Ph
O
(C)
(B) Fehling
(C) NaHSO 3
(D) 2, 4 DNP
which of the following acids: (A) Ethanoic acid and methanoic acid (C) Propanoic acid and ethanoic acid
7
17.
Which one of the following compounds is the best candidate for being prepared by an efficient mixed aldol addition reaction?
OH
O O
(A)
CCH 2 CH(B) CH 3
O
CCHCH 3 CH 2 OH
O O
(C)
CH 2CCHCH3 HO C CH 3
(D)
CCH 2CCH3
18. (A) P giving +ve iodoform test & ve test with Fehling solution. (B) P giving ve iodoform test & +ve test with NaHCO 3 solution. (C) P give +ve Lucas test & ve test with NaHCO 3 solution. (D) P give +ve test with NaHCO 3 & cerric ammonium nitrate solution. 19. Correct order of reactivity of following acid derivatives is MeCON 3 MeCOCl MeCOOCOMe
I II III
20.
(S) :
C=N OH
PCl5 O 2 N
C NH
O
OMe
group during cation rearrangements. NO 2 In question below a statement S and an explanation E is given. Choose the correct answers from the codes A, B, C, D given for each question. (A) S is correct but E is wrong. (B) S is wrong but E is correct. (C) Both S and E are correct and E is correct explanation of S. (D) Both S and E are correct but E is not correct explanation of S. Find the reagent used to bring about following conversions. H H O OH O
8
21.
OH
H (C) HS Et H Me D (D) H Et
SH Me D H
23. The reaction of 4-bromobenzylchloride with sodium cyanide in ethanol leads to (A) 4-bromobenzylcyanide (B) 4-cyanobenzlychloride (C) 4-cyanobenzyl cyanide (D) 4-bromo-2-cyanobenzyl chloride 24. In a compound M ( CO ) 3 NC C=C C2 H 5 NC the number of sigma and pi bonds respectively are (A) 19, 11 (B) 19, 5 (C) 13, 11 25. How many stereoisomers are possible for the adjacent compound
NO2 CHBrMe
(D) 7, 3
CH = CH Me I
26.
(A) 2 (B) 4 (C) 6 The values of the following are given below NO2 NO 2 This is because of
(D) 8
3.9 ( D )
3.39 ( D )
27. (A)
(B) Me shows hyperconjugation effect whereas NO 2 shows R effect in structure II which oppose with each other (C) + I effect of four Me groups nullify I effect of NO 2 group. (D) % of acinitro form of IInd structure is less w.r.t. % of acinitro form Ist structure Alanine (2-amino propanoic acid) exists asat pH 10 CH 3 CH COO (B) NH 2 (C) CH 3 CH COOH NH 2
CH3 CH COOH
NH 2
(D) CH 3 CH COO
NH 3
28.
( I)
( II )
( III )
(D) II > III > I
Correct order of stability of these carbocations is: (A) I > II > III (B) I > III > II (C) II > I > III 29. Column I (reactants) Cl (A) PhCH 3 H 2O OH
( 4)2 (B) CH 3 CH = CH 2 + CO + H2
CO CO Hg (C) CH CH + H 2O PdCl 2 ,CuCl 2 (D) H 2C = CH 2 + O2 H 2O
2+
Column II (product) (p) CH 3CHO (q) PhCHO (r) CH 3CH 2CH 2CHO
30. Column I (organic compounds oxidised by HIO 4 ) HIO4 (A) CH 3CH 2CH CH CH 2 CH3
OH OH
HIO4 (B) PhCH 2CH CH CH 3
Column II (product of HIO 4 oxidation) (p) 2H 2C = O + HCOOH (q) 2CH 3CH 2CH = O (r) 2H 2C = O
OH OH
HIO 4 (C) CH 2 CH 2
OH
OH
OH
OH
10
ANSWER KEY 1. 7. 13. 19. 20. B 2. C 3. C 4. B 5. D A 8. C 9. D 10. B 11. B A 14. D 15. A 16. C 17. B A (This order is only for nucleophilic attack) B 21. D 22. D 23. A 24. A 27. A 28. D 29. A-Q B-R C-P D-P 30. A-Q B-S C-R D-P 6. A 12. BD 18. A 25. D
26. A
11