CHEMISTRY HOUSE

13052023 Advanced Assignment-02 Rankers batch

ORGANIC CHEMISTRY
(for JEE-Mains & Advanced 2024)
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OH

01. dil.
 NaOH
 (A) heat
 (B)
O

(B) HCN
 (C) (CH
2OH)2
 (D) H
2 —Ni
 (E)
+
(E) CHCl
  (F)
3 /KOH
H
2 —Ni
 (G) H
3O
 (H)
+
(H) MeI
 Salt (I) H
3O
 (J) i)
PTS ii) CH3CH2I
 salt (K)
+
(K) H
3O
 (L) i)
PTS ii) PhCH2I
 Salt (M)
+ _ _ +
(D) i)  (N)  
CH3MgI ii) H3O
 (P) i)
i) dil. OH ii) heat
 (Q)
CH2(COOEt)2/EtONa ii) EtO Na / CH3I

+
(Q) H  (R)
3O / heat i)
CH3MgI (excess) ii) hydrolysis
 (S) CH 3OH/ dry HCl
  (T)

Structure of (T) is :

Me Me Me Me
O OMe
O Me
OMe (b) O O
(a) OMe *(c) OMe (d) Me
Me Me Me
Me Me Me Me
Me

+ _
N Me3I _ _
02. OH
, heat
 (A) i)  (B)
ozonolysis ii) OH , then heat

Ph
_ +
(B) + 2, 2—dimethyl cyclohexanone OH
 (C) i)
Br2 (1eq)/H ii) LDA

Product is :

O
(a) (b)
O

O O

O
(c) (d)
O

O O

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03. An organic compound (A) {C70H140On} on reaction with excess Ac2O gives a product
(B) {C84HmOp} of MW = 1594. (A) can decolourise Br2—H2O but can’t reduce Fehling
solution. (A) on reaction with Bayer’s reagent gives (C) {C70HqOr}. One mole of (C) on
reaction with excess MeMgBr produces ‘V’ litre of gas (X) at N.T.P. (C) on reaction
with excess Ac2O gives a product (D) of MW =MO .
Calculate the value of {Vn — (m + p + q + r + MO)} . Ans : 1975
04. If the reaction sequence given below is carried out with 15 moles of acetylene, the
amount of the product D formed (in g) is ________

The yields of A, B, C and D are given in parentheses.

[Given: Atomic mass of H = 1, C = 12, O = 16, Cl = 35] Ans : 135.80 to 136.20

05.M Considering the reaction sequence given below, the correct statement(s) is/are :

(A) P can be reduced to a primary alcohol using NaBH4.

*(B) Treating P with conc. NH4OH solution followed by acidification gives Q.
*(C) Treating Q with a solution of NaNO2 in aq. HCl liberates N2.
*(D) P is more acidic than CH3CH2COOH.
06. The number of isomeric tetraenes (NOT containing sp-hybridized carbon atoms) that
can be formed from the following reaction sequence is ___ . Ans : 2

07. The number of - CH2 (methylene) groups in the product formed from the following
reaction sequence is : Ans : 0

08. The total number of chiral molecules formed from one molecule of P on complete
ozonolysis (O3, Zn/H2O) is _____. Ans : 2

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