ORGANIC CHEMISTRY (18M)

I.DISTINGUISH TESTS OF ORGANIC COMPOUNDS:

SL.NO
Name of te te!t I"e#t$f$%at$o# of %om&o'#"!
(1 Neutral ferric chloride Only phenols(violet or purple color)
() Sodium bicarbonate Only carboxylic acid(brisk effervescence)
(* Iodo form test All 2-ketones2-aloholsethanalethanol(yello! color crystals)
(+ "ucas test #o distin$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 *ondensation2 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 4-
hydroxyketone is kno!n as aldol condensation1

Aldol condensation takes place in presence of dil base1
21 *anni55aro 6eaction2 #he disproportionation (self-redox) of aldehydes lackin$ 3-
hydro$en atom (as *-),*)O )*)O 6**1*)O etc1) in presence of stron$ base to
form salt of an acid ' a primary alcohol is kno!n as *anni55aro reaction1
(1 *arbylamine test2 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 6eduction2 #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 reaction2 A carbonyl compound on heatin$ hydra5ine and pottassium
hydroxide(;O))in a hi$h boilin$ polar solvent such as ethylene $lycol$ets reduced to
$ive a hydrocarbon1


<1 =sterification 6eaction2 6eaction of an alcohol !ith a carboxylic acid in the presence
of a small >uantity of conc1))SO+ to form an ester is called esterification1
=sterification process is $enerally reversible1
?1 0inkelstein 6eaction2 Alkyl iodides can be prepared by the reaction of alkyl chlorides@
bromides !ith NaI in dry acetone1
A1 Battermann 6eaction2 Battermann reaction is used for obtainin$ chloroben5ene or
bromoben5ene from ben5enedia5onium chloride by treatin$ it !ith *u@)*l or
*u@).r respectively1
C1 Battermann-;och 6eaction2 7hen ben5ene or its derivative is treated !ith carbon
monoxide and )*l in the presence of anhydrous aluminium chloride or *u*l it $ives
ben5aldehyde or substituted ben5aldehyde1
%&1 Iodoform test2 #he compound containin$ methyl $roup bonded to carbonyl $roup
(*)(-*O-) or (*)(-*)1O)-) reacts !ith a>uous NaO) and iodine solution $ives
yello! ppt of Iodoform1
%%1 )ell-Dolhard-Eelinsky 6eaction2 7hen aliphatic carboxylic acid containin$ 3-
hydro$en are reacted !ith chlorine or bromine in presence of small amount of red
phosphorous the correspondin$ 3-haloacids are obtained1
%21 )insber$ #est2 )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
are2
a) -rimary amine2- It $ives sulphonamide !ith hinsber$ rea$ent this sulphonamide is
soluble in NaO) or ;O)1
.) Secondary amine2-7ith hinsber$ rea$entit forms sulphonamide !hich is
insoluble in NaO) or ;O)1
*) #ertiary amine2- #ertiary amine do not react !ith hinsber$ rea$ent because it is
not havin$ replaceable hydro$en1
%(1 )offmann-.romamide 6eaction2 7hen an amide is heated !ith bromine and an
alkali a primary amine containin$ 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 process2 -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 ;olbes Schmith process2 #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 dil1)*l $ives salicylic
acid(2-hydroxy ben5oic acid)1
%<1 6iemer-#iemann 6eaction2 #he reaction of pheonal !ith chloroform or carbon-
tetrachloride in the presence of a>ueos alkali at (+&k follo!ed by hydrolysisof the
resultin$ product $ives salicyldehyde and salicylic acid respectively1
%?1 6osenmund 6eduction2 6eduction of acid chloride (6*O*l)to the correspondin$
aldehyde !ith hydro$en usin$ -d@.aSO+ as catalyst is kno!n as rosenmund
reaction1)ere -d@.aSO+ used as ne$ative catalyst and prevent further reduction to
alcohol1

%A1 Sandmayer 6eaction2 #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 -rocess2 )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 6eaction2 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 reaction2 #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 synthesis2 In !illiamson synthesis!hen an alkoxide or a phenoxide is
made to react !ith an alkyl halidean ether is obtained1In this methodhaloarenes can
not be used for the preparation of alkyl-aryl ethers because of the lo! reactivity of
aryl halides1
2(1 7urt5-0itti$ 6eaction2 #his reaction is used for obtainin$ hi$her alkane from the
halo$en derivatives by usin$ sodium1
Me%a#$!m $# O01a#$% 0ea%t$o#!:
1. H2"0at$o# of A34e#e!:
). De2"0at$o# of a3%oo3!:
*. De2"0at$o# of a3%oo3! to 1$5e Ete0!:
+. Rea%t$o# of ete0 6$t HI
ORGANIC REASONING 7UESTIONS
(1)8o$3$#1 &o$#t! of am$#e! a0e 3o6e0 ta# to!e of %o00e!&o#"$#1 a3%oo3! o0 Ca09o:23$%
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
()) Pe#o3 $! a%$"$% $# #at'0e.
A#!: *<):O) *<):O
-
G )
G
-henoxide ion
-henoxide ion is more stable due to resonance1 So phenol acts as an acid1

(*) A3423am$#e! a0e !t0o#1e0 9a!e! ta# a023am$#e!.
A#!: In arylamines the electron cloud on nitro$en !ill be increased due to the presence of alkyl
$roup(6) (alkyl $roup is a donatin$ $roup)
62 N)2
7hereas in arylamines the electron cloud on nitro$en is decreasin$ due to the presence of
ben5ene rin$ (ben5ene is an electron !ithdra!in$ $roup)1
#herefore alkylamines are stron$er bases than arylamines1
(+) E3e%t0o&$3$% !'9!t$t't$o# (N$t0at$o# ;o0 a3o1e#at$o#; o0 !'3&o#at$o#) ta4e! &3a%e o#
8e#<e#e 6e# 8e#<e#e %o#ta$#! a# e3e%t0o#$% "o#at$#1 10o'&(==CH*; o0 ==OH; o0 ==NH);
o0 ==OCH*)
OR
E3e%t0o&$3$% !'9!t$t't$o# (N$t0at$o# ;o0 a3o1e#at$o#; o0 !'3&o#at$o#) ta4e! &3a%e
o# 8e#<e#e at O0to a#" Pa0a &o!$t$o#! o#32 6e# 8e#<e#e %o#ta$#! a# e3e%t0o#$% "o#at$#1
10o'&(==CH*; o0 ==OH; o0 ==NH); o0 ==OCH*)
A#!: ,ue to the presence of an electron donatin$ $roup on ben5ene the electron cloud increases
at ortho and para positions1 So electrophile !ill attack readily at ortho and para positions1
(,) E3e%t0o&$3$% !'9!t$t't$o# o# 9e#<e#e ta4e! &3a%e at meta &o!$t$o# 6e# a# e3e%t0o#$%
6$t"0a6$#1 $! &0e!e#t (==CHO; ==COOH; ==NO))1
A#!: ,ue to the presence of an electron !ithdra!in$ $roup on ben5ene from the resonance
structures the ortho and para positions contains positive char$e cloud so the electrophile can not
attack at ortho and para positions so it has to attack at only meta position havin$ electron
cloud 1
(-) Ha3oa34a#e! a0e mo0e 0ea%t$5e ta# a3oa0e#e!.
A#!: In )aloarenes the halo$en !hich is present on ben5ene rin$ donates its lone pair of
electrons to ben5ene rin$ !hich results in resonance1 So resonance leads stability and less
reactive1 7hereas in haloarenes no resonance results less stable more reactive1
(.) >eto#e! a0e 3e!! 0ea%t$5e to6a0"! #'%3eo&$3$% a""$t$o# 0ea%t$o#! ta# a3"e2"e!. ?2@
A#!: Nucleophilic addititon rections takes place !hen a nucleophile !ill add to a positively
char$ed carbon1
In ketones 6*O6 the partial positive char$e !hich is present on carbon is
neutralised by t!o alkyl $roups !hich are electron donatin$ $roups !hereas
In aldehydes 6*)O the partial positive char$e !hich is present on carbon is partially
neutrali5ed by only one alkyl $roup1 So ketones are less reactive than aldehydes to!ards
nucleophilic addition1
8. Com&a0e te a%$"$% !t0e#1t! of C3=CH)COOH ; F=CH)COOH; I=CH)COOH.
A#!: F=CH)COOH A C3=CH)COOH A I=CH)COOH
0luorine is more electrone$ative than *l and inturn *l is more electrone$ative than
iodine1 In 0-*)2*OO) 0 is more electrone$ative and electron !ithdra!in$ so )
G
releases
very readily and become stron$ acid than the other compounds1
/. Com&a0e te 9a!$% !t0e#1t! of te fo33o6$#1.
CH*NH); NH*; C-H,NH)
A#!: #he basic stren$ths *)(N)2 8 N)( 8 *<):N)2
In *)(N)2 *)( is a donatin$ $roup so the electron cloud on nitro$en increases1 *)(
2N)2 1
In 2N)( nitro$en contain its o!n lone pair of electrons1
In *<):N)2 *<): is an electron !ithdra!in$ $roup so electron cloud on nitro$en
decreases1 So basic stren$th decreases1
1(. Fo0ma3"e2"e 1$5e! %a##$<a0oB! 0ea%t$o# 6e0ea! a%eta3"e2"e "oe! #ot.
A#!: 0ormaldehyde does not contain -hydro$en the compounds !hich does not contain -
hydro$en under$oes canni5aro/s reaction1
Acetaldehyde does contain -hydro$en so it does not under$o canni5aro/s reaction but it
under$oes aldol condensation1
11.Pe#23 met23 ete0 (a#$!o3e)(a023 a3423 ete0!) 0ea%t! 6$t HI to 1$5e Pe#o3 C Met23
Io"$"e 9't #ot Io"o 9e#<e#e a#" Met23 a3%oo3.
A#!: )I is a stron$ acid !hich !ill cleave the oxy$en and alkyl bond because the Oxy$en and
-henyl bond is lo! reactive1
1). U#3$4e Pe#o3!; a3%oo3! a0e ea!$32 &0ota#ate"1
A#!: In phenol the electron pair present on the oxy$en is taken by the ben5ene rin$ for the
resonance1 So electron cloud decreases on the oxy$en atom of phenol so protanation is not easy
in the case of phenol1
7hereas in the case of alcohol 6 is an electronic donatin$ $roup so the electron cloud
on oxy$en increases 1So the protanation occurs easily in the case of alcohol1
1*. Ca09o:$3$% a%$"! "o #ot 1$5e te %a0a%te0$!t$% 0ea%t$o#! of %a09o#23 10o'&.
A#!: In carboxilic acids the caboxilate ion is resonancely stabili5ed1 i1e the pi electrons are not
localised but they are delocalised bet!een t!o oxy$en atoms of carboxilate ion as sho!n belo!1
1+. ?2 $! $t "$ff$%'3t to &0e&a0e &'0e am$#e! 92 ammo#o32!$! of a3423 a3$"e!@
A#!: Ammonia can react !ith the alkyl halides to form a mixture of primary secondary tertiary
amines but not pure amines1
1,. Ho6 a#$3$#e $! "$ffe0et$ate" f0om N=met23 a#$3$#e 92 %a0923am$#e te!t@
A#!2 Aniline is primary amine and N-methyl aniline is secondary amine1 -rimary amines $ives
carbylamine test to $ive isocynides !hereas secondary amines does not respond for the
carbylamine test1
1-.C3o0oa%et$% a%$" $! a5$#1 $1e0 >a 5a3'e ta# a%et$% a%$".
A#!: Any electron !ithdra!in$ $roup on carboxilic acid increases the acidic stren$th1 In chloro
acetic acid chlorine is the !ithdra!in$ $roup and also electrone$ative element1
17.Control of pH during addition of Ammonia derivatives to
Aldehydes and ketones.
A#!: If the medium is too acidic (lo! p) value) the ammonia derivatives bein$ basic in nature
!ill form their respective salts1
If the medium is lo! acidic (p) value is hi$h) then the protonation of the carbonyl $roup of
aldehyde or ketone !ill not occur1 #his in turn !ill not increase the electron deficiency (or G
char$e) on the carbonyl atom of the carbonyl $roup and hence !eak nucleophiles like Ammonia
derivatives !ill not able to reactive1
So p) must be maintained at (1:1
18. Why benzamide is less easily hydrolysed than methyl benzoate.
Ans: Nitrogen N is less electronegative than Oxygen O , therefore N can
donate its pair of electrons more readily than O. As a result, the magnitude of
+ ve charge on the carbonyl group of benamide is much less than that on
the carbonyl carbon of methyl benoate. !onse"uently during hydrolysis, the
O#
$
ion %ill attac& the carbonyl carbon of methyl benoate more readily
than the carbonyl carbon of benamide.
Co#5e0!$o#!:
DA?AHAR NAEODAYA EIDYALAYA; NIFAMSAGAR.
O01a#$% %em$!t02 Date: 1*=1)=)(1(
C3a!!: GII Ma:. Ma04!: .(
I. Distinguish between the following pairs of compounds by giving a chemical
test.(Any 10).10M
1) C
2
H
5
NH
2
and C
2
H
5
NHC
2
H
5
2) Acetophenone and Benzophenone
3) Phenol and Benzoic acid 4) Ethanal and Propanal
5) Acetaldehyde and Benzophenone 6) Benzoic acid and Ethyl
benzoate
7) Pentan2one and Pentan3one !) Aniline and Enthanol
") 2#ethyl 2 Propanol $ 2 Propanol 1%) Phenol $ Ani&ole
11)) Acetic acid $ Acetaldehyde 12) Acetone $ Acetaldehyde'
13) #ethanol $ Ethanol 14) Phenol $ Benzyl alcohol

II. !plain the following named reactions. (Any ") 10M
1) ()rtz*itti+ reaction' 2) ,atter-ann reaction'
3) Cannizaro.& reaction 5) (illia-&on.& /ynthe&i&
6) *riedel Cra0t.& al1ylation 7) 2o&en-)nd reaction
!) Cle-en&on red)ction' ") Cro&& Aldol Conden&ation
1%) Hell3olhard4elin&1y reaction 11) Co)plin+ reaction
12) Carbyl a-ine reaction 13) 2ie-ertie-ann reaction
14) Ho00-an broa-ide reaction
III. #ive the reasons for the following. (Any 1$) 1%M
1) Cyclohe5anone 0or-& cyanohydrin in +ood yield b)t 26266tri-ethyl
cyclohe5anone doe& not'
2) 7)rin+ addition o0 a--onia deri8ati8e& to the carbonyl co-po)nd&6 P
H
i& to
be controlled'
3) *or-ic acid can +i8e 9ollen.& te&t'
4) Boilin+ point o0 an Aldol i& hi+her than the corre&pondin+ al1ane' (hy:
5) Nitration o0 phenol& +i8e& only ortho and para prod)ct&' ,i8e rea&on'
6) Carbo5ylic acid& do not +i8e characteri&tic reaction& o0 carbonyl +ro)p'(hy:
7) Aniline cannot be prepared by ,abrial Phthali-ide &ynthe&i&'
!) Benzoic acid i& &olid ;hile acetic acid i& li<)id'
") 9here are t;o =NH
2
+ro)p& in &e-icarbazide' Ho;e8er6 only one i& in8ol8ed in
the 0or-ation o0 &e-icarbazone&' '
1%) 7iazoni)- &alt& o0 aro-atic a-ine& are -ore &table than tho&e o0 aliphatic
a-ine&'
11) >etone& are le&& reacti8e to;ard& n)cleophile& than aldehyde&'
12) E5plain the /
N
2
-echani&- ;ith rele8ant e5a-ple 0oc)&in+ on in8er&ion o0
Con0i+)ration $ &teric e00ect'
13) E5plain ;hy i& oNitroPhenol -ore acidic than o#etho5yphenol:
14) Phenol i& -ore acidic than cyclo he5anol'
15) ?n the 0ollo;in+ pair& o0 halo+en co-po)nd&6 ;hich ;o)ld )nder+o /N
2

reaction 0a&ter:

CH
2
@6 CH
2
@6 CH
2
ACHCH
2
@

16) (hich acid o0 each pair &ho;n here ;o)ld yo) e5pect to be &tron+er $ +i8e
rea&on: i) CH
3
CBBH $ CH
2
*CBBH6 ii) CH
2
*CH
2
CH
2
CBBH $ CH
3

CH
2
CH*CBBH
17) Boilin+ point o0 carbo5ylic acid& i& hi+her than that o0 alcohol& o0 &a-e
-olec)lar -a&&6 tho)+h both are ha8in+ BH hydro+en bond'
1!) Halo al1ane& react ;ith >CN to 0or- al1yl cyanide& a& -ain prod)ct ;hile
A+CN 0or-& i&ocyanide& a& the chie0 prod)ct' E5plain'
I&. 'rite the mechanisms of the following. (Any () )M
EtBHH
2
B
1) CH
3
CH
2
CH
2
CH
2
Br C >CN CH
3
CH
2
CH
2
CH
2
CN
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
2
H
5
B
2
N react& ;ith (ith
HNB
2
and +i8e& C
2
H
4
B
3
N
2
' Bn red)ction6 DA. +i8e& a co-po)nd DC. ;ith
-olec)lar 0or-)la C
2
H
7
N' DC. on treat-ent ;ith HNB
2
+i8e& D7. ;hich +i8e
po&iti8e ?odo0or- te&t' ?denti0y A6B6C and 7'(rite the corre&pondin+ reaction&'
() An or+anic co-po)nd contain& 6"'77E carbon6 11'63E hydro+en and re&t
o5y+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' Bn 8i+oro)& o5idation 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
5
H
1%
B +a8e a po&iti8e 2647NP te&t
b)t a ne+ati8e 9ollen.& rea+ent te&t' ?t ;a& o5idized to carbo5ylic acid DB. ;ith
-olec)lar 0or-)la C
3
H
6
B
2
;hen treated ;ith al1aline >#nB
4
)nder 8i+oro)&
condition&' /odi)- &alt o0 DB. +a8e a hydrocarbion DC. on >olbe.& electrolytic
red)ction' ?denti0y A6B and C and ;rite the che-ical e<)ation&'
$) Ho; ;ill yo) brin+ abo)t the 0ollo;in+ con8er&ion& in not -ore than t;o &tep&:
Fi) Propanone to Propene Fii) Benzoic acid to Benzaldehyde
Fiii) Ethyl -a+ne&i)- chloride toPropan1ol'
Fi8) #ethyl -a+ne&i)- bro-ide to2#ethylpropan2ol'
F8) pentan1ol )&in+ a &)itable al1yl halide:
(-.)
Pri-ary al1ylhalide C
4
H
"
Br FA) reacted ;ith Alc'>BH to +i8e co-po)nd DB.'
Co-po)nd DB. i& reacted ;ith >Br to +i8e DC.6 ;hich i& an i&o-er o0 DA.' (hen
DA. i& reacted ;ith /odi)- -etal6 it +i8e& co-po)nd D7.6 C
!
H
1!
that ;a&
di00erent 0ro- the co-po)nd 0or-ed ;hen nB)tylbreo-ide i& reacted ;ith
/odi)-' ?denti0y A6B C and 76 and ;rite the che-ical e<)ation&'
)) Pri-ary al1yl halide C
4
H
"
BrFA) reacted ;ith alcoholic >BH to +i8e co-po)nd FB)'
Co-po)nd FB) i& reacted ;ith HBr to +i8e FC) ;hich i& an i&o-er o0 FA)' (hen
FA) i& reacted ;ith &odi)- -etal it +i8e& co-po)nd F7)6 C
!
H
1!
;hich i& 7i00erent
0ro- the co-po)nd 0or-ed ;hen nb)tyl bro-ide i& reacted ;ith &odi)-' ,i8e
the &tr)ct)ral 0or-)la o0 FA) and ;rite the e<)ation& 0or all the reaction&'
(-.)
An aro-atic co-po)nd DA. ha8in+ -olec)lar 0or-)la C
6
H
6
B react& ;ith 4n
d)&t to +i8e an another aro-atic co-po)nd ;ith &i5 carbon ato-& in it&
-olec)le6 and thi& co-po)nd react& ;ith 0)-in+ /)lph)ric acid to +i8e
co-po)nd DB. ;hich i& 0)&ed ;ith NaBH to +i8e co-po)nd DC.' co-po)nd DC.
react& ;ith CB
2
and 0or-& co-po)nd D7. ;hich in t)rn& +i8e& co-po)nd DE.
in acidic -edi)-' Co-po)nd DE. react& ;ith Acetyl Chloride to +i8e a
co-po)nd D*. ;hich i& a 0a-iliar anti pyretic and anal+e&ic' 7ed)ce the
&tr)ct)re& o0 A6 B6 C6 76 E $ *'
%) An or+anic co-po)nd FA) ;ith -olec)lar 0or-)la C
!
H
!
B0or-& an oran+ered
precipitate ;ith 2647NP rea+ent and +i8e& yello; precipitate on heatin+ ;ith
iodine in the pre&ence o0 &odi)- hydro5ide' ?t neither red)ce& 9ollen&. or
*ehlin+&. rea+ent6 nor doe& it decolo)ri&e bro-ine ;ater or Baeyer.& rea+ent' Bn
dra&tic o5idation ;ith chro-ic acid6 it +i8e& a carbo5ylic acid FB) ha8in+ -olec)lar
0or-)la C
7
H
6
B
2
' ?denti0y the co-po)nd& FA) and FB) and e5plain the
reaction& in8ol8ed'
(-.)
?denti0y the rea+ent& A6B6C676E $*0ro- the 0ollo;in+ or+anic con8er&ion'
C
6
H
5
NB
2
*eGHCl A FCH
3
CB)
2
B B Br
2
GH
2
B C H
2
BGH
C
7
NaNB
2
G HCl
* HB*
4
E
&I. 'rite the I/0A* names of the following.(Any %) 1M
1) FBH)CH
2
FNB
2
) CH FCl)= CH
2
= CH
2
=CBBH 2) FCH
3
)
3
CCHAClC
6
H
4
?p
3) CH*
2
CBrCl* 4) ClCH
2
C CCH
2
Br
5) FCH
3
)
2
C
6
H
4
FBC
2
H
5
) 6) FCH
3
)
3
C CH
2
CH
2
B = CHCH
2
CH
3

7) CH
3
CFBH)FCH
3
)BCH
2
CH
3
!) C
6
H
5
CH
2
CH
2
CBBCHFCH
3
)
2

P0a%t$%e Pa&e0 (Or$anic chemistry)
C3a!!: GII Ma:. Ma04!: .(
1. G$5e o#e e:am&3e 6$t eH'at$o# of ?'0t<=F$tt$1 0ea%t$o#. 1M
). 8o$3$#1 &o$#t of a# A3"o3 $! $1e0 ta# te %o00e!&o#"$#1 a34a#e. ?2@ 1M
*. N$t0at$o# of &e#o3! 1$5e! o#32 o0to a#" &a0a &0o"'%t!. G$5e 0ea!o#. 1M
+. Ca09o:23$% a%$"! "o #ot 1$5e %a0a%te0$!t$% 0ea%t$o#! of %a09o#23 10o'&.?2@ 1M
,. ?2 $! Fo0m$% a%$" $! mo0e !t0o#1e0 ta# A%et$% a%$"@ 1M
-. G$5e o#e e:am&3e 6$t eH'at$o# of Gatte0ma## 0ea%t$o#. 1M
.. A#$3$#e $! 6ea4e0 ta# C2%3oe:23am$#e. ?2@ 1M
8. ?2 "oe! 80om$#at$o# of a#$3$#e; e5e# '#"e0 5e02 m$3" %o#"$t$o#! 1$5e );*;,=
t0$90omoa#$3$#e $#!ta#ta#eo'!32. 1M
/. G$5e o#e e:am&3e of ea% of te fo33o6$#1:
a) Ca##$<a0oB! 0ea%t$o# 9) ?o3ff >$!#e0 Re"'%t$o# )M
1(. ?0$te IUPAC #ame to te fo33o6$#1:
CH* C3 COOH
| | 80
a) CH* = CH I CH I CH) ICOOH 9) NO)
)M
|
NO)
OH
11. ?0$te te fo33o6$#1 (G$5e eH'at$o#! o#32):
a) ?$33$am!o#B! S2#te!$! 9) F0$e"e3 C0aftB! a3423at$o# )M
OR
?0$te te fo33o6$#1 (G$5e eH'at$o#! o#32):
a) Ro!e#m'#" 0ea%t$o# 9) C3eme#!o# 0e"'%t$o#.
1). Ho6 6$33 2o' "$!t$#1'$! 9et6ee# C)H,NH) a#" C)H,NHC)H,; 9a!e" o#
%em$%a3 te!t. G$5e eH'at$o#!. )M
1*. E:&3a$# te fo33o6$#1:
a) Pe#23am$#e $! mo0e !o3'93e $# HC3 ta# $# 6ate0.
9) A#$3$#e %a##ot 9e &0e&a0e" 92 Ga90$a3 Pta3$m$"e !2#te!$!. )M
1+. A%%o'#t fo0 te fo33o6$#1:
a) 8e#<o$% a%$" $! !o3$" 6$3e a%et$% a%$" $! 3$H'$".
9) >eto#e! a0e 3e!! 0ea%t$5e to6a0"! #'%3eo&$3e! ta# a3"e2"e!. )M
1,. A%%o'#t fo0 te fo33o6$#1 o9!e05at$o#!:
a) O:$"at$o# of To'3e#e to 8e#<a3"e2"e 6$t C0O* $! %a00$e" o't $# &0e!e#%e of
A%et$% a#2"0$"e.
9) Me3t$#1 Po$#t of a# a%$" 6$t e5e# #'m9e0 of Ca09o# atom! $! $1e0 ta# to!e of
$t! #e$19o'0! 6$t o"" #'m9e0 of %a09o# atom!. )M
1-. E:&3a$# 62 $! o=N$t0oPe#o3 mo0e a%$"$% ta# o=Meto:2&e#o3@ )M
1.. E:&3a$# 62@
a) Te "$&o3e mome#t of C3o0o9e#<e#e $! 3o6e0 ta# tat of %2%3oe:23%3o0$"e@
9) G0$1#a0" 0ea1e#t! !o'3" 9e &0e&a0e" '#"e0 a#2"0o'! %o#"$t$o#!. )M
18. &=D$%3o0o9e#<e#e a! $1e0 Me3t$#1 Po$#t a#" So3'9$3$t2 ta# to!e of o= a#"
m= $!ome0!. D$!%'!!. )M
1/. ?0$te te IUPAC #ame to te fo33o6$#1:
a) (CH*)*CCHJC3C-H+I=&; 9) CHF)C80C3F; %) C3CH)C CCH)80 *M
)(. ?0$te te me%a#$!m of te fo33o6$#1 0ea%t$o#:
EtOH=H)O
CH*CH)CH)CH)80 K >CN CH*CH)CH)CH)CN *M
)1. De%0$9e te me%a#$!m 92 6$% te H2"0o:23 10o'& atta%e" to a# a0omat$% 0$#1 $!
mo0e a%$"$% ta# te H2"0o:23 10o'& atta%e" to a# a3423 10o'&. Ho6 "oe! te
&0e!e#%e of #$t0o 10o'& $# &e#o3 affe%t $t! a%$"$% %a0a%te0@
OR
?0$te te me%a#$!m of te 0ea%t$o# of HI 6$t Meto:2meta#e. *M
)). ?0$te IUPAC #ame! of te fo33o6$#1 %om&o'#"!.
a) 9) (CH*)+ %) CH*CH) = O I CH( CH*)CH)CH*
*M
)*. Ho6 "o 2o' "$!t$#1'$! P0$ma02; Se%o#"a02 a#" Te0t$a02 a3%oo3!. *M
)+. De!%0$9e te fo33o6$#1:
a) C0o!! A3"o3 Co#"e#!at$o# )M
9) 8) He33=Eo3a0"=Fe3$#!42 0ea%t$o# 1M
),. Give plausible eplanation for ea!h of the follo"ing#
$i% Cy!loheanone forms !yanohydrin in good yield but &'&'()
trimethyl!y!loheanone does not.
$ii% *here are t"o +,H& groups in semi!arbazide. Ho"ever' only
one is involved
in the formation of semi!arbazones.
$iii% -uring the preparation of esters from a !arboyli! a!id and
an al!ohol in
the presen!e of an a!id !atalyst' the "ater or the ester should be
removed
as soon as it is formed.
./
&(. Give simple !hemi!al tests to distinguish bet"een the follo"ing
pairs of !ompounds.
a% A!etophenone and 0enzophenone
b% 1henol and 0enzoi! a!id
!% 2thanal and 1ropanal
./
&7. Write short note on #
a% Ho3mann4s 0romamide rea!tion
b% Carbylamine rea!tion
!% Coupling rea!tion
./
&8. Give the stru!tures of A and 0 in the follo"ing rea!tions.

,M
OR
A# o01a#$% %om&o'#" LAB a5$#1 mo3e%'3a0 fo0m'3a C)H,O)N 0ea%t! 6$t ?$t HNO) a#"
1$5e! C)H+O*N). O# 0e"'%t$o#; LAB 1$5e! a %om&o'#" LCB 6$t mo3e%'3a0 fo0m'3a C)H.N.
LCB o# t0eatme#t 6$t HNO) 1$5e! LDB 6$% 1$5e &o!$t$5e Io"ofo0m te!t. I"e#t$f2 A;8;C a#"
D.?0$te te %o00e!&o#"$#1 0ea%t$o#!.
)/. An organi! !ompound !ontains (5.776 !arbon' 11.(.6 hydrogen
and rest oygen.*he mole!ular mass of the !ompound is 8(. 7t does
not redu!e *ollens4 reagent but forms an addition !ompound "ith
sodium hydrogensulphite and give positive iodoform test. 8n
vigorous oidation it gives ethanoi! and propanoi! a!id. Write the
possible stru!ture of the !ompound. 9/
OR
a) A %om&o'#" LAB 6$t mo3e%'3a0 fo0m'3a C,H1(O 1a5e a &o!$t$5e );+=DNP te!t 9't a
#e1at$5e To33e#B! 0ea1e#t te!t. It 6a! o:$"$<e" to %a09o:23$% a%$" L8B 6$t mo3e%'3a0 fo0m'3a
C*H-O) 6e# t0eate" 6$t a34a3$#e >M#O+ '#"e0 5$1o0o'! %o#"$t$o#!. So"$'m !a3t of L8B
1a5e a 2"0o%a09$o# LCB o# >o39eB! e3e%t0o32t$% 0e"'%t$o#. I"e#t$f2 A;8 a#" C a#" 60$te te
%em$%a3 eH'at$o#!. *M
9) Ho" "ill you bring about the follo"ing !onversions in not more
than t"o steps:
$i% 1ropanone to 1ropene $ii% 0enzoi! a!id to 0enzaldehyde
&/
.;. Ho" are the follo"ing !onversions !arried out:
$i% 1ropene to 1ropan)&)ol.
$ii% 0enzyl !hloride to 0enzyl al!ohol.
$iii% 2thyl magnesium !hloride to 1ropan)1)ol.
$iv% /ethyl magnesium bromide to &)/ethylpropan)&)ol.
$v% pentan)1)ol using a suitable alkyl halide:
9/
OR
a' 1rymary alkylhalide C
<
H
5
0r $A% rea!ted "ith Al!.=8H to give
!ompound >04. Compound >04 is rea!ted "ith =0r to give >C4'
"hi!h is an isomer of >A4. When >A4 is rea!ted "ith ?odium
metal' it gives !ompound >-4' C
8
H
18
that "as di3erent from the
!ompound formed "hen n)0utylbreomide is rea!ted "ith
?odium. I"e#t$f2 A;8 Ca#" D; a#" 60$te te %em$%a3 eH'at$o#!. *M
b% Ho" the follo"ing !onversions !an be !arried out:
$i% 1ropene to propan)1)ol
$ii% 2thanol to but)1)yne
&/