VIBRANT ACADEMY ORGANIC CHEMISTRY

IRP Class Test-2

(India) Private Limited Target IIT ADVANCE-2020
IRP ADVANCE TIME : 60 MIN.
Integer type questions :
1. Number of compound which will react with NaHCO3
OH
OH COOH OH OH
NO2
, , , ,
NO2
NO2

OH
2. OH 
x mol

HI
OH

value of x ?

3. How many compounds have faster substitution rate than CH3–Cl ?

Me O
CH3–I , Cl , , ,
Cl O Cl Ph C CH2 Cl

OH NH2 CH3 Cl NO NO2 O

C CH C CH3
4. , , , , , ,
H

x = number of compounds which have rate faster than benzene in EAS

y = number of compound which are o/p directing

xy
then ?
4

5. X = Number of compound which show C-N coupling with PhN2+

NH2 N N

y = number of amines which will form stable diazonium salt

Ph NH
CH3– CH2– NH2 Ph – NH2
CH 3
xy
Find = ?
2
6. In how many reaction ester will form
O
O O
RCO3H ROH
ROH
(1) (2) R C Cl (3) R C NH
2

O COOH
+ +
H
+
H H
(4) R C OH + CH3OH (5) (6)
HO COOH  

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7. The end product of how many reaction are carboxylic acid.
O
C CH3 (i) 1/3 eqi of I2, NaOH
hot alkaline
(1) 
KMnO4
 (2) +
(ii) H

O O +
1 eq. of Br2 H
(3) (4) CH3 C O CH3 H2O
CH3–C–OH

O
HCN H2O CO2 Conc. KOH
(5) Ph C H A B (6) CH 3MgBr + (7) HCHO
HCl H / 
8
2 1
7
3 CH CH2
HBO
8. (i) 4
x = position of OH group in the product
6
5

6
7 5 H3O+
(ii) 2 y = position of –OH group in the product
8 4 3
1
9

CH3
4 OMDM
(iii) CH 3 C CH CH2 z = –OH group in the product
3
2 1
H2O
CH3
Then x + y + z = ?

COONa OH

Re d hot
9. (1) Soda lime (2) Zn (3) CH  CH
Cu tube

OH
+
H3PO2
H +
(4) PhN+2Cl– (5) Ph – SO3H (6) H
 
Find the value of 'x'
(x = number of reaction by which bezene can be produced)

Et Et
OEt RCO3H OEt
10. (1) CH3 Cl low temp.
(2) + (3) CH3 Cl 
H
H H
Et
(1) BH3 , THF
EtOH
(4) CH3 Cl (5) CH3 – CH = CH – CH3
 (2)H2O2 , OH
H
Br2,CCl4
(6) CH3 – CH CH – CH3
x = number of reactions which are stereospecific
y = number of reactions which are stereoselective

xy
then =?
4
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 HBr Br2
11. CCl4
'x' number of products CCl4
'y' number of products

Bayer's RCO3H
reagent
'z' number of products 'p' number of products

x yzp
Then the value of ?
2

12. (1) Heat of hydrogenation for to is negative

(2) equal no. of moles AlCl3 is required in both friedel craft Alkylation and Acylation per mole of benzene
(3) SN2 is a stereoselective reaction
(4) More number of -bonds more will be the heat of hydrogenation
(5) Total number of H replaced by D in the below reaction is 6
O
-
D2O / O D
CH 3 C CH CH CH2 CH3
Then the sum of the correct statements is (For example if 1 and 2 are correct then the sum is 1 + 2 = 3) ?

13. (I) : Number of structurally different dichloro cyclobutane that can be made are equal to (X).
(II) : Number of structurally different dichloro cyclobutane that shows geometrical isomerism are equal to (Y).
Value of (X) + (Y) is equal to

O N
..
OH
NH2OH/H
14. (I) O N
(oxime formation)
OH
O (X) N
.. OH
..
..
O N
NH2OH/H OH
(II) O N
(oxime formation)
..

O OH N
(Y) OH
..
NH2OH/H
(III) O N
(oxime formation)
..

O HO N
(Z) OH
X, Y, Z are the three oximes that can show geometrical isomerism. Sum of all geometrical isomers of
(X + Y + Z) forms are

15. Cholestrol has eight chiral centres

H
H

H H

HO
The specific stereoisomer shown above has 'X' number of theoritical possible diastereomers and answer is
given in the form of X/10.

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 OH OH
16. There are 'X' number of meso stereoisomers and 'Y' number of enantiomeric pairs exist for

Find the value of x + y = ? Cl

17. The number of stereoisomers possible for the below compound (do not change cis/trans configurations of the
olefins) are
O CO2H

OH
OH

18. How many stereoisomers are possible for sucralose.

19. Number of disproportnation and dimerization product formed when C2H5Br and CH3 – CH2 – CH2– Br are
treated with Na in the presence of dry ether is:

20. How many condensation products are possible when ethanal and phenyl ethanal (mixture) is treated with dil.
NaOH.

21. If x = number of reactions from which aldehyde can be obtained.

O H2


(1) R C Cl Pd-BaSO4 (2) RCN + SnCl2 + HCl  (3) RCN 
DIBALH


CH3
O


(i) CrO Cl ,CS

2 2 2 CO,HCl
DIBALH
(4) R C OEt   (5)   (6)  
(ii) H3 O Anh. AlCl
3

Then x = ?

O O



Ag(NH3 )2  Fehling's Re agent

22. (i) R C H 
H2 O
 (ii) CH3 C H 


O OH O



ammonical
(iii) R  C  CH  R'   (iv) Ph C H 
Fehling's Re agent
AgNO3 
O


C H
O
Benedict's reagent


Tollen 's Reagent

(v) CH3 C CH3  (vi) (CHOH)n
CH2OH
(Aldose)

CH2OH
C O
Benedict's reagent
(vii) (CHOH)n

CH2OH
(Ketose)

If x = number of reaction from which positive test is obtained. Then x = ?

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