IIT-JEE CHEMISTRY BY N.J.

SIR ORGANIC CHEMISTRY

DAILY PROBLEM PRACTICE SHEET

1. (a) 1 < 2 (b) 1 < 2 (c) 1 < 2 (d) 1 < 2 (e) 1 > 2

+
2. H /∆
(A) CH3–CH2–CH2–CH–CH3 → CH3–CH2–CH=CH–CH3 (Major)
OH +
CH3–CH2–CH2–CH=CH2 (Minor)
OH
CH3 H+ / ∆
(B) → +

(Major) (Minor)

(C) H+ / ∆
→ +

OH (Major) (Minor)

CH3 CH3 CH3 CH3

⊕
(D) CH3–C–CH2 → CH3–C–CH2 → CH3–C–CH2–CH3 → CH3–C=CH–CH3 → CH2=C–CH2–CH3
⊕
CH3 CH3 CH3
(Major) (Minor)

CH3
2H SO / ∆
4
3. (a) CH3–C–CH3 → CH3–C=CH2
OH CH3

H3C CH3 H3C CH3 CH3 CH2

(b) CH3–CH2–C–CH–CH3 → CH3–CH2–C=C–CH3 + CH3–CH2–CH–C
CH3

⊕
CH2 ⊕
(c)  → 
→ +

(Major) (Minor)

1
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F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahindra Showroom), BSNL Office Lane,
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 ⊕ ⊕
CH–CH2–CH3 ⊕
CH2–CH3 CH2–CH3 CH2–CH3 CH2–CH3
(d) +

(Major) (Minor)

(e)

CH3 CH3 CH2

(f) CH3–CH2–CH–C–CH3 → CH3–CH2–CH–C–CH3 → CH3–CH2–C=C + CH3–CH2–CH–C
CH3 CH3
CH3 CH3 CH3 CH3

(Major) (Minor)
⊕
+
(g) ⊕
(major) (minor)

(h) +

H H
(j) ⊕
H
CH3 CH3

(k) ⊕
⊕

⊕
+
(l)
(major) (minor)

(m) +

(major)
⊕
⊕ +
(n)
(major) (minor)
⊕
(o) ⊕

CD2 CD2

(p) +

(minor) (major)

2
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ETOOS Academy Pvt. Ltd.
F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahindra Showroom), BSNL Office Lane,
Jhalawar Road, Kota, Rajasthan (324005)
 CH3 CH2
D D D D
(q) D + D D

(major) (major)
Cl
(r)

(s) ⊕ +

CH3 CH2
⊕C–CH3 C–CH3
+
4. (a) OH 
H

→ ⊕ 
→ 
→

6
H+ 
→
(b) 
→
⊕
⊕ 5 3 1
2
OH

6 2
⊕
5 3
4

CH2
H + CH3–CH CH2
(c) CH3–CH–CH2–CH2–CH2 → CH3–CH–CH2–CH2–CH2 + H2 → → CH3–CH
⊕
•• O CH2
O OH ⊕ O
18 H •O
• H H

H
5. (a) (b) Cl
Cl
Cl
HCl
(c) (d) CH3–C=CH2 → CH3–C–CH3

Cl CH3 CH3

(e) HI
→

3
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ETOOS Academy Pvt. Ltd.
F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahindra Showroom), BSNL Office Lane,
Jhalawar Road, Kota, Rajasthan (324005)