Organic Low Achievers Material

ORGANIC CHEMISTRY (18M)

I.DISTINGUISH TESTS OF ORGANIC COMPOUNDS:

SL.NO

Name of te te!t

I"e#t$f$%at$o# of %om&o'#"!

1

 Neutral ferric chloride

Only phenols(violet or purple color)



Sodium bicarbonate

Only carboxylic acid(brisk effervescence)

*

Iodo Iodo for form tes testt

All All 22-ket ketones ones2 2-a -allohol ohols set etha hana nallet ethano hanoll(yel (yello lo! ! col color or cry crystal stals) s)

+

"ucas test

#o distin$uish%& 2& ' & alcohols

,

insber$ test

%& 2& '& amines

-

*arbylamines test

Only primary amines



Sodium metal test

Alcohols(effervescence)

8

2+ ,N test

.oth aldehydes ' ketones (yello! color crystals)

/

#ollen/s test

Only aldehydes(silver mirror formation)

1

0ehilin$/s test

Only aldehydes(red ppt)

Name" Rea%t$o#!: %1

Aldol *ondensation condensation bet!een t!o molecule of an aldehyde or a ketone havin$ atleast one 3-hydro$en atom to form a 4-hydroxyaldehyde or a 4hydroxyketone is kno!n as aldol condensation1

Aldol condensation takes place in presence of dil base1 21

*anni55aro 6eaction #he disproportionation (self-redox) of aldehydes lackin$ 3hydro$en atom (as *-,*O *O 6 **1*O etc1) in presence of stron$ base to form salt of an acid ' a primary alcohol is kno!n as *anni55aro reaction1

1

*arbylamine test 7hen a primary amine is heated !ith alcoholic caustic potash and chloroform an offensive smellin$ compound called carbylamine ( alkyl or arylisocyanide) is formed1

+1

*lemmension 6eduction #he reduction of 8*9O $roup to methyl $roup (8*2) !ith amal$amated 5inc and conc1 *l is kno!n as *lemmension reduction1

:1

7olf-;ishner reaction A carbonyl compound on heatin$ hydra5ine and pottassium hydroxide(;O)in a hi$h boilin$ polar solvent such as e thylene $lycol$ets reduced to $ive a hydrocarbon1

uantity of conc1SO+ to form an ester is called esterification1

=sterification process is $enerally reversible1 ?1

0inkelstein 6eaction Alkyl iodides can be prepared by the reaction of alkyl chlorides@  bromides !ith NaI in dry acetone1

1

Battermann 6eaction Battermann reaction is used for obtainin$ chloroben5ene or  bromoben5ene from ben5enedia5onium chloride by treatin$ it !ith *u@*l or *u@.r respectively1

C1

Battermann-;och 6eaction 7hen ben5ene or its derivative is treated !ith carbon monoxide and *l in the presence of anhydrous aluminium chloride or *u*l it $ives  ben5aldehyde or substituted ben5aldehyde1

%&1

Iodoform test #he compound containin$ methyl $roup bonded to carbonyl $roup (*-*O-) or (*-*1O-) reacts !ith a>uous NaO and iodine solution $ives yello! ppt of Iodoform1

%%1

ell-Dolhard-Eelinsky 6eaction 7hen aliphatic carboxylic acid containin$ 3hydro$en are reacted !ith chlorine or bromine in presence of small amount of red  phosphorous the correspondin$ 3-haloacids are obtained1

%21

insber$ #est insber$ test is employed to distin$uish primary secondary and tertiary amine1 #he rea$ent used in this test is ben5ene sulphonyl chloride1 #he tests are a) rimary amine- It $ives sulphonamide !ith hinsber$ rea$ent this sulphonamide is soluble in NaO or ;O1 .) Secondary amine-7ith hinsber$ rea$entit forms sulphonamide !hich is insoluble in NaO or ;O1 *) #ertiary amine- #ertiary amine do not react !ith hinsber$ rea$ent because it is not havin$ replaceable hydro$en1

%1

offmann-.romamide 6eaction 7hen an amide is heated !ith bromine and an alkali a primary amine containin$ one carbon less than the amide is obtained1 #his reaction is called offmann-.romamide reaction1 #his reaction is very useful for convertin$ a hi$her homolo$ue to next lo!er one1

%+1

;olbe/s-=lectrolysis process reperation of hi$her aFkanes by the electrolysis of sodium or potassium salt of lo!er fatty acids is called ;olbe/s electrolysis reaction1

%:1

;olbes Schmith process #his reaction $ives the method for fixation of *O2 in the  ben5ene rin$1Sodium phenoxide on heatin$ that %2&-%+&* under +-? atm pressure !ith *O $ives sodium salicylate !hich on reaction !ith d il1*l $ives salicylic acid(2-hydroxy ben5oic acid)1

%ueos alkali at +&k follo!ed by hydrolysisof the resultin$ product $ives salicyldehyde and salicylic acid respectively1

%?1

6osenmund 6eduction 6eduction of acid chloride (6*O*l)to the correspondin$ aldehyde !ith hydro$en usin$ [email protected]+ as catalyst is kno!n as rosenmund reaction1ere [email protected]+ used as ne$ative catalyst and prevent further reduction to alcohol1

%1

Sandmayer 6eaction #he convesion of ben5ene dia5onium salt into halo$en of cyano derivative of the parent aromatic hydrocarbon by treatin$ it !ith a mixture containin$ the corrspondin$ salt and the acid is called sandmeyer reaction1

%C1

Saponification rocess ydrolysis of esters in the presence of an alkali is kno!n as saponification1In this process sodium salt of fattyacids(commonly called as soaps)are obtained1

2&1

Stephen 6eaction Nitriles can be reduced to correspondin$ imine !ith stannous chloride in the presence of hydrochloric acid !hich on hydrolysis $ive correspondin$ aldehyde1 #his reaction is called Stephen reaction1

2%1

S!art/s reaction #he synthesis of alkyl fluorides is accomplished by heatin$ an alkyl chloride@ bromide in the presence of a metallic fluoride such as A$0$0 etc1

221

7illiamson/s synthesis In !illiamson synthesis!hen an alkoxide or a phenoxide is made to react !ith an alkyl halidean ether is obtained1In this methodhaloarenes can not be used for the preparation of alkyl-aryl ethers because of the lo! reactivity of aryl halides1

21

7urt5-0itti$ 6eaction #his reaction is used for obtainin$ hi$her alkane from the halo$en derivatives by usin$ sodium1

Me%a#$!m $# O0a#$% 0ea%t$o#!: 1. H2"0at$o# of A34e#e!:

. De2"0at$o# of a3%oo3!:

*. De2"0at$o# of a3%oo3! to $5e Ete0!:

+. Rea%t$o# of ete0 6$t HI

ORGANIC REASONING 7UESTIONS (1)o$3$# &o$#t! of am$#e! a0e 3o6e0 ta# to!e of %o00e!&o#"$# a3%oo3! o0 Ca09o23$% a%$". A#!: In amines alcohols and carboxylic acids there is a presence of hydro$en bondin$1 .ut nitro$en is less electrone$ative than oxy$en so the intermolecular hydro$en bond !hich is  present in amines are !eaker than the correspondin$ alcohols and carboxylic acids1 So boilin$  points of amines are lo!er than that of carboxylic acids and alcohols1

() Pe#o3 $! a%$"$% $# #at'0e. *CN

M

CH 3CH2CH2CH2CN

2) Hydration o0 ethene in pre&ence o0 dilte acid& to +i8e ethanol' 3) 9he dehydration o0 Ethyl alcohol in the pre&ence o0 con' /lphric Acid re&lted the 0or-ation o0 Ethene' &. *omplete the following. (*onversions+ word problems) (% ! %M) ,%M 1) ,i8e the &trctre& o0 A and B in the 0ollo;in+ reaction&'

(-) An or+anic co-pond DA. ha8in+ -oleclar 0or-la C 2H52N react& ;ith (ith

HN2 and +i8e& C 2H43N2' n redction DA. +i8e& a co-pond DC. ;ith -oleclar 0or-la C 2H7N' DC. on treat-ent ;ith HN 2 +i8e& D. ;hich +i8e po&iti8e ?odo0or- te&t' ?denti0y ABC and '(rite the corre&pondin+ reaction&'

) An or+anic co-pond contain& 6"'77 carbon 11'63 hydro+en and re&t

oy+en'9he -oleclar -a&& o0 the co-pond i& !6' ?t doe& not redce 9ollen&. rea+ent bt 0or-& an addition co-pond ;ith &odi- hydro+en&lphite and

+i8e po&iti8e iodo0or- te&t' n 8i+oro& oidation it +i8e& ethanoic and propanoic acid' (rite the po&&ible &trctre o0 the co-pond' (-)

A co-pond DA. ;ith -oleclar 0or-la C 5H1% +a8e a po&iti8e 24NP te&t bt a ne+ati8e 9ollen.& rea+ent te&t' ?t ;a& oidized to carboylic acid DB. ;ith -oleclar 0or-la C 3H62 ;hen treated ;ith alaline >#n 4 nder 8i+oro& condition&' /odi- &alt o0 DB. +a8e a hydrocarbion DC. on >olbe.& electrolytic redction' ?denti0y AB and C and ;rite the che-ical eH to +i8e co-pond DB.' Co-pond DB. i& reacted ;ith >Br to +i8e DC. ;hich i& an i&o-er o0 DA.' (hen DA. i& reacted ;ith /odi- -etal it +i8e& co-pond D. C !H1! that ;a& di00erent 0ro- the co-pond 0or-ed ;hen nBtylbreo-ide i& reacted ;ith /odi-' ?denti0y AB C and  and ;rite the che-ical eo39eB! e3e%t0o32t$% 0e"'%t$o#. I"e#t$f2 A; a#" C a#" 60$te te %em$%a3 e'at$o#!. *M 9) Ho" "ill you bring about the follo"ing !onversions in not more

than t"o steps: $i% ropanone to ropene $ii% 0enzoi! a!id to 0enzaldehyde &/ ;. Ho" are the follo"ing !onversions !arried out: $i% ropene to ropan)&)ol. $ii% 0enzyl !hloride to 0enzyl al!ohol. $iii% 2thyl magnesium !hloride to ropan)1)ol. $iv% /ethyl magnesium bromide to &)/ethylpropan)&)ol. $v% pentan)1)ol using a suitable alkyl halide: 9/ OR 

a' rymary alkylhalide CC4' "hi!h is an isomer of >A4. When >A4 is rea!ted "ith ?odium metal' it gives !ompound >-4' C 8H18 that "as di3erent from the !ompound formed "hen n)0utylbreomide is rea!ted "ith ?odium. I"e#t$f2 A; Ca#" D; a#" 60$te te %em$%a3 e'at$o#!. *M b% Ho" the follo"ing !onversions !an be !arried out: $i% ropene to propan)1)ol $ii% 2thanol to but)1)yne &/