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Question

Cl2/hv Na Br2/hv Mg
CH4 1 2 3 4
DE ether

Br2/KOH NH3 SOCl2 1. CO2

8 Δ
7 6 5 2. NH4Cl

Cu/300oC dil. NaOH/Δ 1. PhMgBr Al (t-BuO)3,

9 10 11 12
2. NH4Cl CH3COCH3

H⊕/Δ H⊕ 1. PhMgBr + CuBr

15 14 13 2. NH4Cl
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Answer

1 CH3-Cl 2 CH3-CH3 3 CH3-CH2Br

4 CH3-CH2-MgBr 5 CH3-CH2-COOH 6 CH3CH2COCl

7 CH3-CH2-CONH2 8 CH3-CH2-NH2 9 CH3-CH=O

OH O
| ||
10 CH3-CH=CH-CH=O 11 CH3
-CH=CH-CH-Ph 12 CH3
-CH=CH-C-Ph

O CH3 CH3
||
13 CH3-CH-CH2-C-Ph 14 15
|
Ph HO Ph Ph
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Question
An organic compound (A) (C18H20O) on reductive ozonolysis gives (B) (C10H12O)
and (C) (C8H8O2). (B) gives iodoform test also produces oxime (D) (C10H13ON) on
treatment with NH2OH. (D) reacts with PCl5 to give (E) which on hydrolysis gives
(F) C8H11N along with a monobasic acid (G) having molecular mass 60. (F) on
treating with NaNO2 + HCl gives (H) which on oxidation gives a dibasic acid (I). (I)
on heating gives anhydride (J), (J) on heating with liquid NH3 gives (K). (K) on
treating with KOH followed by treating with compound (L) and hydrolysis gives (I)
and alanine (lowest molecular mass optically active α-amino acid). (J) on reaction
with benzene + anhydrous AlCl3 followed by Zn-Hg/HCl followed by conc. H2SO4
followed by NH2NH/OH− followed by Pd-C and heat gives anthracene. Also, (J)
on hydrolysis followed by treating with PCl5 followed by Rosenmund reduction
gives (M). (M) on reaction with hydrazine gives a cyclised compound (N).
Compound (C) on mild oxidation gives (O) which gives effervescence with
NaHCO3. (O) on treatment with HI produces p-hydroxybenzoic acid and CH3−I.
Give structures from (A) to (O) with reactions involved.
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Answer CH3 O COOH

CH3−C−NH−CH2
CH2−C=CH ||
E
O J O O
A
H3C
CH3 O OCH3
OCH3 CH2−NH2 O
CH3 F
K NH
CH2−C=O CH3
B O
CH3 G CH3COOH Br−CH−COOH
L
CHO
CH2−OH CH3
C H CHO
CH3 M
OCH3 CH3 CHO
CH2−C=N−OH COOH CH N
D I N
CH3 COOH CH N
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Question

An organic compound (A) gives Lucas test within test 5 to 10 minutes. 0.051 g of
(A) when treated with MeMgI gives 11.2 ml of methane at STP. (A) on dehydration
gives (B) which on ozonolysis gives two isomeric compounds (C) and (D). (D)
gives positive Tollens test but not iodoform test while (C) gives positive iodoform
test but not Tollens test. (D) on oxidation gives (E). The silver salt of (E) contains
59.6% silver. (C) on heating with dilute NaOH gives (F) which on treating with
sodium hypoiodite solution gives yellow compound along with sodium salt of
acid (G). (G) on decarboxylation gives (H) which on treating with sodium
hypoiodite solution gives yellow compound along with sodium salt of acid (G).
(G) on decarboxylation gives (H) which on treating with t-Bu-Cl/AlCl3 followed by
H2/Ni gives (I). (I) on monochlorination gives four mono-chloro structural isomers.
(C) on treating with Mg-Hg followed by hydrolysis gives (J). (J) on periodic
oxidation gives back (C) , and (J) on treating with dil H2SO4 undergoes a
rearrangement to give (K). (K) forms oxime but doesn’t give Fehling’s test. Assign
structures from (A) to (K).
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Answer
CH3 CH3
| |
A CH3-CH2-CH - CH-CH3 F CH3-C=CH-C-CH3 J CH3- C - C - CH3
| | | || | |
OH CH3 CH3 O OH OH
O CH3
|| |
B CH3-CH2-CH = C-CH3 G CH3-C=CH-C-ONa K CH3- C - C - CH3
| | | ||
CH3 CH3 CH3 O

C CH3-C=O H CH3-C=CH2
| |
CH3 CH3
CH3
|
D CH3-CH2-CH=O I CH3-CH-CH2-C-CH3
| |
CH3 CH3

E CH3-CH2-COOH
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