Distinguishing Test WORKSHEET

ORGANIC CHEMISTRY WORKSHEET Distinguish between the following pi!s of o!gni" "o#poun$s % Pair of Organic compounds

Name of the Test

Reagent

Observations wrt with each compound

Equations where applicable .

Chlorobenzene and Benzyl Chloride

Silver nitrate test

Alcoholic AgNO3

Benzyl Chloride- Will give white ppt of silver chloride Chlorobenzene-No reaction.

CCl# and C$Cl3

Carbyla!ine %est

n-propyl alcohol and ,so propyl alcohol

,odo ,odoffor! or! %est

&ri!ary a!ine li'e C$3 N$  N$( alcoholic )O$*NaO$ NaO$ NaO$, ,(

C$Cl3 + gives offensive s!elling isocyanide gas. CCl# + No reaction. ,so propyl alcohol is C$3C$O$  C$3 gives yellow ppt of C$,3

C$3C$O$  C$3CO C$3  C$3

NaO$ NaO$, ,(

n-propyl alcohol +No reaction 1thanol gives yellow  ppt of C$,3

C$3CO C$3 /NaO,  C$,3 / C$3COONa C$3C$(O$  C$3C$O

NaO$ NaO$, ,(

0ethanol +No reaction 1thanol gives yellow  ppt of C$,3  benzyl alcohol+No reaction

C$3C$(O$  C$3C$O

0ethanol and  ethanol

1thanol and  benzyl alcohol

,odo ,odoffor! or! %est

,odo ,odoffor! or! %est

Important points

 benzyl chloride has chlorine attached to side chain so  precipitate will be for!ed . in the case of   chloro benzene no AgCl precipitate will be for!ed as the chlorine  benzene bond is strong d"e to resonance... R-NH2 + CHCl3 + 3KOH --------> RNC + 3KCl + 3H2O

C$3C$O / NaO,   C$,3 / $COONa

C$3C$O / NaO,   C$,3 / $COONa

Alcohols with str"ct"re si!ilar to C$3C$-O$ 2  2$ or al'yl gro"p.

Acetaldehyde and for!aldehyde

,odofor! %est

NaO$,(

Acetaldehyde gives yellow ppt of C$,3 5or!aldehyde +No reaction

C$3C$O / NaO,   C$,3 / $COONa

Acetaldehyde and acetone

%ollen9s 2eagent %est

ammoniacal silver nitrate solution (Tollens’ reagent) [Ag(NH3)2]+

Acetaldehyde- gives shiny silver !irror  Acetone - No reaction

C$3C$O / [Ag(NH3)2]+ +OH-  C$3COONa /Ag/$(O/N$3

Benzaldehyde ,odofor! %est and acetaldehyde

NaO$,(

C$3C$O / NaO,   C$,3 / $COONa

Bezaldehyde and ,odofor! %est acetophenone

NaO$,(

3-pentanone and (- pentanone

,odofor! %est

NaO$,(

Acetaldehyde gives yellow ppt of C$,3 Benzaldehyde +No reaction Acetophenone gives yellow ppt of C$,3 Benzaldehyde +No reaction (- pentanone gives yellow ppt of C$,3 3-pentanone +No reaction

Acetophenone and Benzophenone

,odofor! %est

NaO$,(

C$3CO C:$; /NaO,  C$,3 / C:$;COONa

&henol and Benzoic acid

 Ne"tral ferric chloride test

5eCl3

&henol and

Ne"tral ferric

5eCl3

Acetophenone gives yellow ppt of C$,3 Benzophenone +No reaction &henol gives violet colo"ration Benzoic acid-No reaction. &henol gives violet

4ive positive iodofor! test. Aldehydes and 'etones having at least one !ethyl gro"p lin'ed to the carbonyl carbon ato! 6!ethyl 'etones C$3CO--7 are o8idised by NaO, 6NaO, is for!ed when  NaO$ reacts with ,( 7 ,odofor! test cannot be "sed as both will react .

C$3CO C:$; /NaO,  C$,3 / C:$;COONa C$3CO C3$

Whenever the co!po"nd has (-one in na!e "s"ally iodofor! test can be "sed.

Whenever phenol is given "se ferric chloride test.

Acetic acid

chloride test

1thanol and Acetic acid

,odofor! %est

1thyla!ine and Aniline

Azo dye test

NaO$,(

colo"ration Acetic acid-No reaction. 1thanol gives yellow  ppt of C$,3 Acetic acid +No reaction

C$3C$(O$  C$3C$O C$3C$O / NaO,   C$,3 / $COONa

NaNO2/HCl (nitrous aci is !orme in situ) !ollo"e #$ #eta na%&t&ol

Aniline "it& NaNO2/HCl (nitrous aci is !orme in situ) give #en'ene ia'oniu m c&lorie "&ic& reacts "it& #eta na%&t&ol to !orm orange %%t o! an a'o $e 1thyla!ine reacts to !orm an alco&ol instea o! $e

C:$; N$( / NaNO2+ HCl  C:$; N(Cl /NaCl/$(O

1thyla!ine- %"rbidity is seen which dissolves in al'ali ?iethyla!ine%"rbidity is seen which is insol"ble in al'ali &henol gives violet colo"ration Acetic acid-No reaction. (-!ethyl -(- propanol will give t"rbidity i!!ediately.

C*H,O2Cl + C($; N$( C*H,O2 N$ C($;

@-propanol will not give t"rbidity at roo! te!perat"re

C$3C6C$3 7Cl  C$3

1thyla!ine and ?iethyla!ine

$insberg 2eagent

en'enesul%& on$l c&lorie (C*H,O2Cl) is Hins#erg’s reagent

&henol and Aniline

 Ne"tral ferric chloride test

5eCl3

@-propanol and (-!ethyl -( propanol

"cas %est

ucas reagent (conc HCl an .nCl2)





C:$;O$ / 5e/3 = 6C:$;O735e>

C$3C6C$3 7O$ / HCl(.nCl2)   C$3

&henol and Cyclohe8anol.

 Ne"tral ferric chloride test

5eCl3

5or!ic acid and Acetic acid

%ollen s reagent test

ammoniacal silver nitrate solution (Tollens’ reagent) [Ag(NH3)2]+

&henol gives violet colo"ration Acetic acid-No reaction. for!ic acid red"ces %ollen s reagent to !etallic silver b"t acetic acid doesn t.

C:$;O$ / 5e/3 = 6C:$;O735e>

$COO$ / (=Ag6N$37(>/ / (O$- --- (Ag / CO( / ($(O / #N$3 C$3COO$ / =Ag6N$37(>/ ---- no silver !irror 

5or!ic acid is the only acid to give / test for tollens n fehlings