Organic Review 4 Marking

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Organic Review – 04

1. Br
l
i) CH3 CHCH3 + CH3 CH2 CH2 Br
ii) CH3 CH2 CH2 Br
iii) CH3 CH2 Cl
iv) CH3 CH2 CH2 Cl
v) CH3 CH2 CH2 OH
vi) CH3 CH = CH2
vii) CH3 CH2 CH2 CN
viii) CH3 CH2 NH2
ix) CH3 CH2 CH2 – O – CH3 (m%Odk) CH3 CH = CH2 (iq¿)
x) CH3 CH2 C ≡ C – CH2 CH3 (m%Odk) CH2 = CH2 (iq¿)

δ+
2. H H H H
δ+l l l l
i) H – C = C – Br δ − H – C = C – H + Br − + H2 O
δ+ l l
H H
−ሷOH

δ+
ii) CH3 CH2 CH2 – Br δ − CH3 CH2 CH2 OH + Br −

−ሷ OH

CH3 CH3
l δ− l +
iii) CH3 – C – Br CH3 – C −ሷ
l l OH
CH3 CH3

CH3
l
CH3 – C – OH
l
CH3

3.
PBr3 / PBr5
i) CH3 CH2 CH2 OH CH3 CH2 CH2 Br

O HCN
ll H + /H2 O
CH3 CH2 CH2 – C – OH CH3 CH2 CH2 CN

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O
ii) NaOH(aq) PCC ll
CH3 CH2 Br CH3 CH2 OH CH3 – C – H

O O
ll ① id¡ H2 SO4 ll NaOH
CH3 CH2 CH – C – H CH3 – CH = CH – C – H
l ② H2 O ∆
OH
① LiAlH4
② H + /H2 O
PBr3
CH3 CH2 CHCH2 OH CH3 CH2 CHCH2 Br
l l
OH Br KCN
CH3 CH2 CH – CH3 – CN
l
CN

O
iii) CH3 CH2 CH2 OH PCC ll
CH3 CH2 – C – H
Zn(Hg) NaOH
HCl O ∆
ll
CH3 CH = CH – CH – CH3 CH3 CH = CH – CH– C – H
l l
CH3 CH3

OH − /KMnO4 OH Br CH3
l PBr3 l l
CH3 CHCH – CH– CH3 CH3 CH – CH – CH3
l l l l
OH CH3 Br CH3

COOH CH3 CN
l l H + /H2 𝑂 l KCN
CH3 CHCH – CH– CH3 CH3 CH – CH– CH3 – CH3
l l l
COOH CN CH3

iv) CH3 CH2 – OH CH3 CH – CH2 CH2 – CH– CH3


l l
CN CN

CN CN
l l
v) CH3 CH2 – OH CH3 CH – CH– CH2

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4.
i) CH3 CH2 OD
OLi
l
ii) CH3 – C – H CH3 CH2 OH
l
H
OLi OH
l l
iii) CH3 – C – CH3 CH3 – CH – CH3
l
H
O O
ll ll
iv) CH3 – C – H CH3 – C – OH

O
ll
v) CH3 – C – CH3

Organic Review – 05

5. OSO3 H OH
l l
i) CH3 CH2 CH – CH3 CH3 CH2 CH – CH3
ii) CH3 CH2 OH
iii) CH3 CH2 OH
iv) CH3 CH2 CH2 OH
OH
l
v) CH3 CH – CH3
vi) CH3 CH2 OH
+
O− MgBr OH
l l
vii) CH3 CH2 – CH – CH3 CH3 CH2 CH – CH3
viii) CH3 CH2 Br
ix) CH3 CH2 Br / H3 PO3
x) CH3 CH2 Cl / POCl3 + HCl
xi) CH3 CH2 C − Na+ / CH3 CH2 – O – CH3
O O
ll ll
xii) CH3 – C – H CH3 – C – OH

O
ll
xiii) CH3 – C – CH3
xiv) CH3 CH2 OH / N2

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