2743219-PRACTICAL-ORGANIC-CHEMISTRY-FOR-IIT-JEE-ENTRANCE-TEST-by-S-K-sinha-See-Chemistry-Animations-at-sinhalab-com.pdf

MASTERING ORGANIC CHEMISTRY

1. Test of unsaturation (a) addition of H 2,

(b)

By-- S.K.SINHA

1

1 π ≡  ≡ 1 mole H 2

addition of Br2\  CCl 4 or Bromine Bromine water water

*Phenolic compounds gives light yellow ppt with Br  2w   ater. *Aromatic amines – gives ppt with Br  2/H2O (c)

Bayer’s Reagent  – discharge the colour colour of dil, cold, cold, alkaline KMnO KMnO4t  o pink or brown.

(d)

Terminal alkynes gives red/brown ppt with Cu 2Cl2/NH4OH – due to Copperalkylide.

(e) Terminal alkyne gives white ppt with tollens reagent (f) undergoes ozonolysis. 2. Test of OH–group (i) evolves H2g   as with Na metal.

(ii) (iii) (iv) (v)

(vi)

gives red soln. with ceric ammoniam nitrate. gives ester with acetic anhydrides, acid chloride, acids. gives halides with PCl5, PX3, anhy. ZnCl2/  conc. HCl or SOCl 2. lucas test (anhy. ZnCl2 / Conc. HCl) 3° →F   ormation of turbidity →i  mmediate 2° →  →F   ormation of turbidity within 5 minutes. 1° →N   o turbidity appears – Victor Mayer Test  – (i) P/I2/Δ (a) Red soln. – nitrolic acid salt → 1 0 (ii) AgNO2.

Alcohol

(iii) NaNO2/  conc. H 2SO4 (vii)

Silver alkylide.

(iv) OH –  with Cu/300°C

(b) blue soln. of Pseudonitrol → 2 0

(c) No colour – 3° alcohol (a) 1° Alcohol →aldehyde (b) 2° Alcohol →K   etone (c) 3° Alcohol →a  lkene

(3) Test of Phenolic group (a) soluble in NaOH – Insoluble in NaHCO3(  Picric acid is only alcohol soluble in NaHCO 3) (b) Phenol gives red colour with alc. FeCl3

(c) Phenols – undergoes acetylation & Methylation. (4) Test of ether linkage (a) Ethers – insoluble in H2O. (b)

with HI – gives alcohol and alkyl Iodide

(c) with excess HI – only alkyl Iodide (5) Test of Carbonyl groups (a) Phenyl hydrazine &HCl brown crystalline compound of phenyl hydrazone. (b) 2,4 – DNPH (Brady’s reagent) Red ppt (c) NH 2OH/H+  Oxime (d) Reduced to alkanes by (i)Wolff = Kishner reduction – NH 2 NH2/KOH (ii)Clemeneson (ii)Clemeneson reduction →  Zn(Hg)/HCl 6. Test of aldehydes only (a) Red ppt with Fehling soln. – Cu2O.` (c) (e) (f) 7. Test of (a) (b)

Red ppt with Benedict’s soln.

Cu 2O

Silver mirror (Ag) with Tollen’s Reagent. (d) Pink colour with Schiff’s reagent.   ldehydes with α – Hydrogen with with dil base – NaOH NaOH Aldol condensation – A without no α–   hydrogen with conc. NaOH/KOH. Cannizzaro Reaction  – aldehydes without Ketones Wine red colour with sod. nitroprusside aliphatic methyl ketones gives ppt with NaHSO3. (c) On Reduction – gives 2° alcohol.

8. Test of corboxylic corboxylic acid (a) With NaHCO3–   effervescence of CO 2 (c) Amides with NH3/Δ (e)

(b)

(b)

PCl 5, PCl3, SOCl2 acid chloride

(d)

Acetic acid gives blood red colour with FeCl 3

HCOOH– also gives oxidation with (i) Tollen’s Reagent (ii) Fehling solution

9. Test for dibasic acid (a) Oxalic acid .

CO +CO2 +H 2O

B-7. JAWAHAR NAGAR.Main Road ,Kota.

(b)

(iii) HgCl 2

(iv) Br  2

Malonic acid →CH3COOH + CO2 Ph-0744-2422383 .Mo-93149-05055

2  

(c) (e) 10. Test of Test of

MASTERING ORGANIC CHEMISTRY By-- S.K.SINHA Succinic acid → Succinic anhydrides. (d) Maleic acid →Maleic anhydrides Glutaricacid → Lactones (f) Adipicacid →Cyclo pentanone – hydroxy acids → on heating gives Lactides –hydroxy acids – on heating undergoes dehydration to give   .unsaturated acid. R–CH=CH2 –COOH + H2O

11. Test for Halo acids (a) α –haloacids α –hydroxy acid (b) β-haloacid β –hydroxy acid (c) ν and higher haloacids loctones 12. Test of Esters : Esters are neutral, water insoluble compound, with fruity smell Ester on reduction with LiAlH 4o   r Na/C 2H5OH gives two mole of alcohol. Ester on hydrolysis (saponification)gives acid and alcohol. 13. Test of Anhydrides : (a) Anhydrides reacts with water to form two moles of acid. (b) Anhydrides react with PCl5t  o form acid chloride.

(c)

with NH3 –form amide and acid.

(d)

On reduction with LiAlH4 –gives two moles of alcohol.

14. Test of aliphatic halogen compounds All halides (except vinyl). when heated with aq. NaOH. followed by acidification and with AgNO 3  gives white,l  ightYellow or dark yellow ppt. 15. Test for amines : 1. All amines are basic in nature. 2. All amines are soluble in acids. 3. Reacts with excess RCl to form quanternary ammonium halides. 4. With NaNO2/Cl or HNO 2

(a)

aliphatic – P–amines form alcohol and alkene and evolve N2g   as. (except – CH 3 –NH2)

(b)

Aromatic–p–amine gives di-azonium salt (0–50°C). Alkaline soln. of β –Napthol gives red to orange coloured dye with diazonium salt. Secondary amine:  Form yellow emulsion of N–Nitrosoamine. N– nitrosoamine with a crystal of phenol and few drowps of conc. H2SO4p   roduces intense blue colour. (Libermaan’s Nitroso Reaction)

(c)

16. Reaction given by only primary and secondary amine. (a) 1° & 2° amines are acetylated acid benzoylated. (b) evolve H2g   as with Na metal. (c) gives alkane with G.R. (d) gives N–halogenated amines with halogen/NaOH. 0   mines only. 17. Reaction given by 1 a Carbyl amine test all 1° amines when heated with CHCl3a  nd alc. KOH form isocyanides (Foul smelling (a) odour). (b)   1° amine when heated with CS 2a  nd HgCl 2f  orm isothiocyanates having Haloform mustard oil reaction– smel lof mustard oil. 18. Test for Cyanides (a) Cyanides on reduction with LiAlH4/  Na/CaH 5OH or H2/Ni form 1° amines. (b) Cyanides on hydrolysis gives carboxylic acid and ammonia. 19. Test for Isocyanides (a) Isocyanides on reduction with LiAlH4/Na/C2H5OH or H2/Ni form secondary methyl amine. (b) Isocyanides on hydrolysis gives p–amines and HCOOH. 20. Test for aliphatic nitro compound (a) Reduction with Sn/HCl (acidic medium) – 1° amine. (b) Reduction in neutral medium Zn/NH4Cl or Sn/CaCl 2 –  Hydroxylamine (c)

On reaction with NaNO2/conc. H2SO4

1°–nitro – nitrolic acid – red soln. in NaOH 2°–nitro– Pseudonitrol–blue soln. R–O–NO. (a) on Redn. gives alcohol (Sn/HCl) 21  Alkyl nitrite (b) on hydrolysis gives alcohol 22. Test for amides (a) Smell of ammonia on heating. (b) amides gives 1° amine with LiAlH4                   

(c)

Amides gives cyanides with P2O5

B-7. JAWAHAR NAGAR.Main Road ,Kota.

Ph-0744-2422383 .Mo-93149-05055.