Some useful equations for organic problems

Unit 11
Ethanol

NaOH HCl
CH3CH2Cl → →
Anhydrous ZnCl2
H2 O PCl3 /Py
CH2 = CH2 → →
H2 SO4
PCl5
→
i) CH3 Mgi SOCl2
HCHO → CH3CH2OH →
ii) H2 O/H+
HBr
→ CH3CH2Br
i) LiAlH4 H2 SO4
CH3CHO→ → CH2 = CH2 (Ethene)(Dehydration)
ii) H2 O 443K
i) LiAlH4 Na2 Cr2 O7 /H+ (O)
CH3COOCH2CH3→ → CH3CHO → CH3COOH(Oxidation)
ii) H2 O (O)
PCC
→ CH3CHO
Or Cu/573K
CH3 COOH
→ CH3COOCH2CH3 (Ethyl acetate)
H+
(Esterification)
Molecular formula: C2H6O
Hint: i) Doesn’t form turbidity with Lucas reagent at room temperature
ii) Gives red colour in Victor-Meyer’s test.
iii) Liberates H2 gas with metallic Na
Isopropyl alcohol
H2 O Na2 Cr2 O7 /H+ (O)
CH3CH=CH2 → → CH3COCH3 → CH3COOH
H2 SO4 (O)

→
HCl Hint: Molecular formula: C3H8O
Anhydrous ZnCl2 i) Forms turbidity slowly with Lucas reagent
i) CH3 Mgi PCC ii) Gives blue colour in Victor-Meyer’s test.
CH3CHO → → CH3COCH3
ii) H2 O/H+ Or Cu/573K

Unit 12
HCN H3 O+
Acetaldehyde → →

PCC 2CH3 OH
CH3CH3OH → → CH3-CH(OCH3)2
HCl

i) O3 NH2 OH
Molecular formula: C2H4O
CH3-CH=CH-CH3 →
ii) Zn/H2 O
→ CH3CH=NOH Hint: Reduces Tollens reagent or
Hg𝑆O4 NH3 Fehling’s solution or oxidized by
CH≡CH +H2O → → CH3CH=NH
H3 𝑆O4 Tollens reagent or Fehling’s
∆ CH3CHO (O) solution
(CH3COO)2Ca+(HCOO)2Ca → → CH3COOH
Gives positive haloform test
Pd/BaSO4 2[H]
CH3COCl +H2 → → CH3CH2OH
LiAlH4
(Rosenmund’s reduction)
i) SnCl2 /HCl (H) Zn−Hg/HCl
CH3CN → → CH3CH3(Clemmensen reduction & Wolf-Kshner reduction
ii) H3 O+ or NH2 NH2 /C2 H5 ONa
(Stephen’s reaction)
[Link] Δ
→ → CH3CH=CHCHO (Aldol condensation)
Acetone

PCC NH2 NH2

→ →
Or Cu/573K

i) O3 NH3
→ →
ii) Zn/H2 O Δ

Hg𝑆O4 (O)
CH3-C≡CH→ → CH3-COOH +HCOOH
H3 𝑆O4 Conc.HNO2
CH3COCH3 2[H]
→
NaBH4
∆
(CH3COO)2Ca →
Zn−Hg/HCl
→ CH3CH2CH3(Clemmensen reduction & Wolf-Kshner
or NH2 NH2 /C2 H5 ONa
CH3COCl + (CH3)2Cd → reduction)
Mg−Hg
→ (pinacol reduction)
H3 𝑂

Cl3 NaOH
→ CCl3COCH3 → CHCl3 +CH3COONa (Haloform reaction)
NaOH
Molecular formula: C3H6O
Hint: Does not reduces Tollens reagent or Fehling’s solution or does not oxidized by
Tollens reagent or Fehling’s solution
Gives positive haloform test
Benzaldehyde
Pd NH3
C6H5CHO + H2 → →
BaSO3

i) CrO2 Cl2 /CS2 CH3 CHO

→ → C6H5CH=CHCHO (Claisen – Schmidt Condensation)
ii) H3 O+ [Link]

(Etard reaction)
CO/HCl CH3 COCH3
→ → C6H5CH=CHCOCH3(Claisen – Schmidt Condensation)
AlCl3 /CuCl [Link]

NaOH
(Gattermann-Koch reaction) → C6H5CH2OH + C6H5COONa( Cannizaro reaction)

HCHO
→ C6H5CH2OH + HCOONa (Crossed Cannizaro reaction)
[Link]

[Link]
→ (Benzoin condensation)

(CH3 CO)2 O
→ C6H5CH=CHCOOH (Perkins’ reaction)
CH3 COONa

CH2 (COOH)2
→ C6H5CH=CHCOOH( Knoevenagal reaction)
Py
C6 H5 NH2
→ C6H5CH= NC6H5 (Schiff’s base)
H+ /∆

Molecular formula C7H6O

Hint: Oxidized by Tollens reagent not by Fehling’s solution (Aromatic aldehydes don’t reduce Fehling’s
solution.
Acetic acid
K2 Cr2 O7 /H+ (O) Na or NaOH NaOH
CH3CH2OH → CH3CHO→ → CH3COONa → CH4 (Decarboxylation)
(O) CaO
𝐸𝑙𝑒𝑐𝑡𝑟𝑜𝑙𝑦𝑠𝑖𝑠
→ CH3CH3 (Kolbe’s
H2 O PCl5 or SOCl2
CH3CN → → CH3COCl electrolysis)
H+

i) CO2 CH3 CH2 OH

CH3MgBr → → CH3COOCH2CH3 (Esterification)
ii) H2 O H+ CH3COOH H+

H2 O 4[H]
CH3COOCH2CH3→ → CH3CH2OH
H+ LiAlH4

H2 O HI/red P
CH3COCl → → CH3CH3
H+ 473K

H2 O i) NH3
(CH3CO)2O → → CH3CONH2
H+ ii) ∆

P2 O5
→ (CH3CO)2O (Dehydration
∆
Cl2 /red P
→ CLCH2COOH (HVZ reaction)

Molecular formula C2H4O2

Hint: Gives brisk effervescence with NaHCO3
 Unit 13
Nitro ethane
Sn/HCl
→ CH3CH2NH2 (Reduction in acidic medium)
6[𝐻]
KNO2 Zn/NH4 Cl
CH3CH2Br → → CH3CH2NHOH(Reduction in neutral medium)
Ethanol/∆ 4[𝐻]

HCl/H2 O
CH3CH3→
HNO3
675K
CH3CH2NO2 →
Boil
CH3CH2OH (Hydrolysis)

CH3 COOOH i) KOH

CH -CH=N-OH → → CH3CHO (Nef carbonyl synthesis)
(O) ii) H2 O/H+

Nitro benzene
Sn/HCl
→ C6H5NH2
6[𝐻]
Electrolytic reduction
→ C6H5NH2
weakly acidic
Ni or Pt/𝐻2
→ C6H5NH2
Zn/NH4 Cl
→ C6H5NHOH(Reduction in neutral medium)
4[H]
Conc.HNO3 /H2 SO4 Fe/H2 O
C6H6 → → C6H5NO(Reduction in neutral medium)
330K 2[H]
SnCl2 /KOH
→ C6H5N=NC6H5(Reduction in alkaline medium)

Zn/NaOH
→ C6H5NH-NHC6H5(Reduction in alkaline medium)

Conc.HNO3 /H2 SO4

Hint: Also called as oil of mirbane →
373K

Conc.HNO3 /H2 SO4

→
473K
Ethanamine

H2 /Ni or Pt CH3 COCl

CH3CH2NO2 → → C2H5NHCOCH3
Sn/HCl or Fe/HCl Py

Na(Hg)/C2 H5 OH i) HNO3 (NaNO3 +HCl)

CH3CN →
4[H]
CH3CH2NH2 →
𝑖𝑖) H3 O
CH3CH2OH

Excess NH3 CHCl3 +KOH

CH3CH2Br → → CH3CH2NC (carbylamine reaction)
CS5
→ CH3CH2N=C=S (Mustard oil reaction)
[Link]
Molecular formula: C2H7N
Hint: Give positive carbylamine reaction/isocyanide test and Mustard oil reaction

Aniline
H2 / Pt,680K HCl
C6H5NO2 → → C6H5NH3Cl
Sn/HCl

NH3 / Cu2 O C6 H5 COCl

C6H5Cl →
200℃
C6H5NH2 →
Py
C6H5NHCOC6H5
(Schotten-Baumann reaction)
NH3 / anhydrous ZnCl2 NaNO2 + HCl (HNO2 )
C6H5Cl → → C6H5N2Cl(Diazotization)
300℃ 273−278K

CS5
→ C6H5N=C=S (Mustard oil reaction)
[Link]

Molecular formula: C6H7N

Hint: Give positive carbylamine react/isocyanide test and Mustard oil reaction
Benzene diazonium chloride
H3 PO2 + H2 O/CuCl
→ C6H6 (Reduction)
Or CH3 CH2 OH

Cu3 𝐶l2 /HCl

→ C6H5Cl
Or Cu/HCl

Cu3 Br2 /HBr

→ C6H5Br Sandmeyer reaction &
Or Cu/HBr

C6H5NH2→
NaNO2 + HCl (HNO2 )
C6H5NH2 CuCN/KCN
→ C6H5CN Gatterman reaction
273−278K

HBF4
→ C6H5F (Baltz – schiemann reaction)
∆

H2 O
→ C6H5OH
∆
i) HBF4
→ C6H5NO2
ii) NaNO2 /Cu

C6 H6
→ C6H5- C6H5 (Gomberg reaction)
NaOH
KCN H2 O/H+
→ CH3CH2CN→ CH3CH3COOH SnCl3 /HCl
` → C6H5NHNH2(Reduction)
Or Na2 SO3
CH3CH2Br→
AgCN H2 O/H+ C5 H5 OH
→ CH3CH2NC→ CH3CH3NH2 →
C2 H5 OH pH 9−10
(Coupling reaction)
C5 H5 NH2
→
pH 4−5