Target: Jee (Advanced) 2017: Course: VIJETA & VIJAY (ADP & ADR) Date: 30.04.2017

ORGANIC CHEMISTRY
TARGET : JEE (ADVANCED) 2017
Course : VIJETA & VIJAY (ADP & ADR) Date : 30.04.2017 NO. 6
TEST INFORMATION
DATE : 03.05.2017 PART TEST(PT)-04
Syllabus : Aromatic Compound, Carbonyl Compounds, Carboxylic Acid & Their Derivatives and Grignard
Reagent.
DPP Syllabus : Aromatic Compound, Carbonyl Compounds, Carboxylic Acid & Their Derivatives and Grignard Reagent.
DPP No. # 6
Total Marks : 175 Max. Time : 120 min.
Single correct Objective ('–1' negative marking) Q.1 to Q.10 (3 marks, 2 min.) [30, 20]
One or more correct objective ( no negative marking) Q.11 to Q.21 (4 marks, 2 min.) [44, 22]
Assertion and Reason ('–1' negative marking) Q.22 to Q.23 (3 marks, 3 min.) [06, 06]
Comprehension ('–1' negative marking) Q.24 to Q.32 (3 marks, 2 min.) [27, 18]
Integer type ('–1' negative marking) Q.33 to Q.41 (4 marks, 3 min.) [36, 27]
Match the Following (no negative marking) Q.42 to Q.45 (8 marks, 6 min.) [32, 24]
O
|| NaOH
P4O10 MeMgBr
1. C – NH2   P    Q 
I2 (Iodoform reagent)
 R, compound R is %

 H3O
O
||
(A) C – CH3 (B) COOH
O
||
(C) C (D)

2. [X]  Number of fractions
Find X & total number of fractions :
OH OH
| |
(A) Ph  CH  COOH ; (1) (B) Ph  CH  CH3 ; (2)
OH OH
| |
(C) Ph  CH  COCl ; (1) (D) CH3  CH  COOH ; (1)
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Page No. -1
HNO3 HNO3 (NH4)2S NaNO2,HCl H2O, Sn ,HCl
3. M N O P Q R
H2SO4 H2SO4 0°C
R is :
OH
(A) (B) (C) (D)

NO2
4. A mixture of two aromatic compounds (A) and (B) was separated by dissolving in chloroform followed by
extraction with aqueous KOH solution. The organic layer containing compound (A) when heated with
alcoholic solution of KOH produced a compound C (C7H5N), associated with an unpleasant odour. The
alkaline aqueous layer on the other hand, when heated with chloroform and then acidified gave a mixture of
two isomeric compounds (D) and (E) of molecular formula C7H6O2 . Identify (A).
(A) PhNC (B) PhOH (C) Ph–NH2 (D) Salisaldehyde
5. The intermediate of the following reaction is :
(A) (B) (C) (D)
6. Consider the following sequence of reaction and identify the end product(R) :
COOH
SOCl2 AlCl3 Zn-Hg
P Q R
CH2Ph HCl
O
O
O
(A) (B) (C) (D)
Ph
Ph
Page No. -2
7. In the following sequence of reactions :
Ph
M
Ph O
–
N PhCH2OH + Ph–COO
O3
Q M + N.
Zn/H2O
The compound Q is :
Ph
(A) Ph–CH2–CH=CH–Ph (B) =CH–CH 3 (C) (D) Ph–CH=CH–Ph
Ph
8. Predict the major product of given reaction.
N H / KOH / H O (A )

2 4 2

Wolf Kishner reduction Major ; Product A is :
(A) (B)
(C) (D)

H
9.  ( A ) , Product (A) is :


(A) (B) (C) (D) | |
OH OH
OH OH
10. , This conversion can be achieved by :
OH O
(A) Me2CO/H+, H3O, KMnO4/HO– (B) Me2CO/H+, KMnO4,H3O
(C) KMnO4/NaO4, Me2CO/H+, H3O+ (D) KMnO4/NaIO4, H3O+, Me2CO/H+
Page No. -3
Na ( excess ) NaOEt ( excess )
11.* (P)          (Q) Major
Acetone 
Select the correct statements :

(A) (P) is a single stereoisomer (product). (B) (Q) is a single stereoisomer (product).
(C) (P) is an SN2 product. (D) (Q) is an E2 product (major).
 18
H /H O
12.*  2  (Product)
The correct observations about the above mentioned reaction are :
(A) (Major product) (B) (Major product)
(C) Reactant has 1S, 2S configuration. (D) Major product has 1S, 2R configuration.
13.* 
 product + a gas
The correct statement(s) about above reaction

(A) The product is a racemic mixture
(B) Racemisation occurs due to enolisation
(C) The reaction passes through a cyclic transition state
(D) The intermediate of the reaction is a carbanion.
(i) CHCl NaOH, 

3
14.*        (P > Q) % yield
(ii) H 
Select the correct options :

(A) Boiling point , (P > Q) (B) Melting point , (Q > P)
(C) Water solubility , (P < Q) (D) Acid Strength , (Q < P)
15.* Which of the following is/are true statement(s) :

(A) Diazocoupling in aniline is carried out in sightly acidic medium.
(B) Carbonyl compounds undergo electrophilic as well as nucleophilic addition reaction.
(C) Secondary amines give insoluble precipitate with aqueous alkaline PhSO2Cl.
(D) Benzaldehyde reacts faster with grignard reagent than benzene-1,2-dicarbaldehyde.
Page No. -4
16.* Compound A (C5H7OCl) reacts rapidly with ethanol and catalytic amount of acid to form a plesant smelling
substance, B (C7H12O2) . A also reacts with H2O to form C with neutralisation equivalent of 100. A, B and C
all react with Br2 water. Acid C, which can also be obtained by acidic hydrolysis of B which is oxidised to new
acid D (C4H6O3) and CO2. D on heating with soda lime gives acetone. Identify A to D .
(A) A = CH3– C – CH2 – C – Cl (B) B = CH3– C – CH2 – C – OEt

CH2 O CH2 O
(C) C = CH3– C – CH2 – C – COOH (D) D =

CH2 O
17.* Identify A, B, C, D, E and F in the following :
Cl Cl
CH2NO2 CH2OH
(A) A = (B) D =
Cl Cl
Cl
(C) F = (D) G =
Cl Cl
18.* Identify A, B, C, and D in the following :
(A) D is Cis (B) D is trans (C) B is Cis (D) B is trans
19.* Primary (1º) amine group is formed in :
(A) NaHS (B) Br / KOH

 2
(C) CH NH / Cu O / 
3 2 2 (D) Zn / HCl
  
Page No. -5
CONH2
20.*
Which statement(s) is/are correct :

(A) Reduced product of P and Q will be metamers to each other.
(B) By dry distillation of hydrolysed products of P with Ca(OH)2, gives benzophenone.
(C) Hydrolysed product of Q, reacts with NaNO2 + HCl followed by reaction with phenol, gives orange red
dye.
(D) Electrophile involved in the formation of Q is dichlorocarbene.
21.* The product/s of the following reaction is/are :
Product/s
(A) (B)
(C) (D)
22. Statement-1 : CCl3CHO forms an isolable crystalline hydrate.

Statement-2 : Electron withdrawing chlorine atoms stabilise hydrate by intramolecular H-bonding.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1.
(C) Statement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.
23. Statement-1 : CH3MgBr can not be prepared in cold aqueous solution.

Statement-2 : Water molecules stablise grignard molecules by H–bonding.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1.
(C) Statement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.
Comprehension # 1
Methyl red is commonly used as indicator for acid base titrations. It is prepared by treating NaNO2/HCl with
anthranilic acid and the resulting solution is mixed with N,N dimethylaniline and shaked well the solution for
some minutes to get “Methyl Red”.
Given : (anthranilic acid)
Page No. -6
24. Which is most likely to be “Methyl Red” ?
(A) (B)
(C) (D)
25. The two organic materials anthranilic acid and N,N dimethylaniline used in preparation of methyl Red can be
best distinguished by :
(A) HCl solution (B) Br2 water (C) CHCl3/KOH (D) FeCl3
Comprehension # 2
The relative comparision of equilibrium constants of addition of RMgBr on four carbonyl compounds has been
shown by the graph below.
26. Which compound corresponds to H if the four given compounds are :

(A) P – NO2C6H4CHO (B) C6H5CHO (C) P – MeOC6H4CHO (D) CH3COCH2CH3
27. Which compound corresponds to G if the four given compounds are :
(A) CH3CHO (B) C6H5COCH3 (C) C6H5CHO (D) C6H5COC6H5
Comprehension # 3
CH – CH – CH Cl 2O
3
  2 2 X 
 
 +
AlCl3 H3 O
28. Which of the following compound is 'P' ?
(A) (B) (C) (D)
29. S is a well known pain killer which of the following is 'R' ?
(A) (B) (C) (D)
Page No. -7
Comprehension # 4
Observe the following sequence of reaction
O3 CHCl 3/NaOH
X Y Z W U
Zn/H2O (2) H2O (–H 2O)
30. The product Y is
O
O
(A) (B)
OH
OH
(C) (D)
31. The product U is

O O
(A) (B)
O
O
O
O
O
(C) (D)
O
32. Compound (Y) on reaction with CO2/NaOH followed by CH3–C–Cl and pyridine produces :
COOH OCOCH3
OCOCH3 COOH
(A) (B)
COOCH3 COOH
COOH COOCH3
(C) (D)
33. Number of positions electrophilic substitution which takes place when salicylic acid is reacted with bromine
water ?
34. The number of stereoisomers of the product obtained in the following reaction is :
Ph  CH  CH  O +
|
Me
( )
Page No. -8
35. In the following sequence of reaction number of Nucleophilic substitution is :
(1) O / 
36.   2   ?
(2 ) dil. H2SO 4 / 
Total number of organic products formed (major, minor all).
O 
37. 3
 NH2OH / H
   
excess
The total number of isomeric products (including stereomers) formed at the end of the reaction is :
38. How many aromatic diazonium chlorides of xylene can be reduced to meta-xylene by H3PO2?
H PO2 , 
3    (m-Xylene)
39. Find the total number of groups with which the Grignard Reagent (CH3MgBr) can react.
40. How many types of Grignard reagent can be used to prepare the following alcohol, by using different Ketones.
Et
|
Me – C – CH(Me 2 )
|
OH
41. Observe the following reaction,
NH OH. HCl
2 H2SO4 KOH, boil
H Acidificat ion 
'X'  (           H N – CH – CH – CH – COOH
1) ( 2) (3 ) ( 4) 2 2 2 2
molecular mass of 'X' is :
Page No. -9
42. Column-I Column-II
(A) OH (p) Aromatic ring substitution

 

(B) CH CHO / OH

3    (q) Nucleophilic addition
 
(C) HNO H SO (r) Condensation reaction

32 
4
KCN / H
(D)   
 (s) Formation of more than one organic products
43. Match the column

Column I Column II

(i ) OH
(A) MeCO(CH2)4COMe   
 (p)
( ii) H / 

OEt
(B) (CH2)4  (q)
(C) PhCHO + 3
 
CH COO –
 (r) (Ph)2 C — COO –
|
OH

OH
(D) PhCOCOPh  (s)
Page No. - 10
44. Column-I Column-II
(Reactions) (Features)
HNO
3
(A)   (p) KH/KD = 1
H2SO 4
(B) Cl / Fe (q) KH/KD > 1

2
(C) Conc.H SO (r) Deactivated reactant

 2
4
(D) C H OH / H (s) Ortho and para substituted products are major

25  
(t) Meta substituted product is major.
45. Column – I Column – II

(Compounds) (Type of possible reactions)
(A) (p) Nucleophilic addtion
(B) (q) Aliphatic nucleophilic substitution
(C) (r) Elimination
(D) (s) Electrophilic addition reaction
(t) Electrophilic substitution reaction
Page No. - 11
ANSWER KEY
DPP NO. # 5
1. (C) 2. (B) 3. (A) 4. (B) 5. (A)
6. (AC) 7. (ACD) 8. (AD) 9. (BC) 10. (BD)
11. (BCD) 12. (ABC) 13. (ACD) 14. (BCD) 15. (CD)
16. (ABD) 17. (BCD) 18. (BCD) 19. (BCD) 20. (ABC)
21. (C) 22. (D) 23. (C) 24. (C) 25. (A)
26. (B) 27. (C) 28. (ACD) 29. (AC) 30. (C)
31. (D) 32. (A) 33. 4 34. 3 35. 7
36. 4 37. 4 38. 4 39. 6 40. 6
41. 12 42. 15 43. 5
44. (A)  (s) ; (B)  (r) ; (C)  (p) ; (D)  (q)
45. (A)  q ; (B)  q,s (C)  p,r ; (D)  q)
46. (A) p, q, r ; (B) p, s ; (C) q, r ; (D) s
47. (A)  q, r, s ; (B) p, q, r, s ; (C)  p, q, r, s ; (D)  q, r
Page No. - 12

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ORGANIC CHEMISTRY

TARGET : JEE (ADVANCED) 2017

Find X & total number of fractions :

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

5. The intermediate of the following reaction is :

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

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

Select the correct statements :

The correct observations about the above mentioned reaction are :

(A) (Major product) (B) (Major product)

The correct statement(s) about above reaction

(i) CHCl NaOH, 

Select the correct options :

15.* Which of the following is/are true statement(s) :

(A) A = CH3– C – CH2 – C – Cl (B) B = CH3– C – CH2 – C – OEt

(C) C = CH3– C – CH2 – C – COOH (D) D =

17.* Identify A, B, C, D, E and F in the following :

18.* Identify A, B, C, and D in the following :

(A) D is Cis (B) D is trans (C) B is Cis (D) B is trans

19.* Primary (1º) amine group is formed in :

(A) NaHS (B) Br / KOH

Which statement(s) is/are correct :

21.* The product/s of the following reaction is/are :

22. Statement-1 : CCl3CHO forms an isolable crystalline hydrate.

23. Statement-1 : CH3MgBr can not be prepared in cold aqueous solution.

Given : (anthranilic acid)

26. Which compound corresponds to H if the four given compounds are :

28. Which of the following compound is 'P' ?

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

29. S is a well known pain killer which of the following is 'R' ?

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

31. The product U is

Total number of organic products formed (major, minor all).

41. Observe the following reaction,

molecular mass of 'X' is :

(A) OH (p) Aromatic ring substitution

(B) CH CHO / OH

(C) HNO H SO (r) Condensation reaction

43. Match the column

(B) Cl / Fe (q) KH/KD > 1

(C) Conc.H SO (r) Deactivated reactant

(D) C H OH / H (s) Ortho and para substituted products are major

(t) Meta substituted product is major.

45. Column – I Column – II

(A) (p) Nucleophilic addtion

(B) (q) Aliphatic nucleophilic substitution

(C) (r) Elimination

(D) (s) Electrophilic addition reaction

(t) Electrophilic substitution reaction

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