ORGANIC CHEMISTRY (18M)
ORGANIC CHEMISTRY (18M)
I.DISTINGUISH TESTS OF ORGANIC COMPOUNDS: I.DISTINGUISH TESTS OF ORGANIC COMPOUNDS:
SL.NO SL.NO
N
Naamme e oof f tte e ttee!!tt II""ee##tt$$ff$$%%aatt$$oo# # oof f %%oomm&&oo''##""!!
1
1 Neutral ferric chloride Neutral ferric chloride Only phenols(violet or purple color)Only phenols(violet or purple color)
SSooddiiuum m bbiiccaarrbboonnaattee OnOnlly y ccaarrbbooxxyylliic c aacciidd((bbrriissk k eeffffeerrvveesscceennccee))
*
* IoIodo do foforrm tm tesestt All 2All 2--kekettononeses22-a-allohohololssetethahananalleetthahanonoll(y(yelellolo! c! cololor or crcryyststalals)s)
+
+ ""uuccaas s tteesstt ##o o ddiissttiinn$$uuiisshh%%&& 2 2&& ' ' && alcohols alcohols
,
, iinnssbbeerr$$ tteesstt %%&&22&& ' '&& amines amines
-- **aarrbbyyllaammiinnees s tteesstt OOnnlly y pprriimmaarry y aammiinneess
SSooddiiuum m mmeettaal l tteesstt AAllccoohhoollss((eeffffeerrvveesscceennccee))
8
8 22+ + ,,NN tteesstt ..ootth h aallddeehhyyddees s ' ' kkeettoonnees s ((yyeelllloo! ! ccoolloor r ccrryyssttaallss))
/
/ ##oolllleenn//s s tteesstt OOnnlly y aallddeehhyyddeess((ssiillvveer r mmiirrrroor r ffoorrmmaattiioonn))
1
Name" Rea%t$o#!:
%1 Aldol *ondensation condensation bet!een t!o molecule of an aldehyde or a ketone havin$ atleast one 3-hydro$en atom to form a hydroxyaldehyde or a
4-hydroxyketone is kno!n as aldol condensation1
Aldol condensation takes place in presence of dil base1
21 *anni55aro 6eaction #he disproportionation (self-redox) of aldehydes lackin$ 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 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
<1 =sterification 6eaction 6eaction of an alcohol !ith a carboxylic acid in the presence of a small >uantity of conc1SO+ 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 $ives yello! ppt of Iodoform1
%%1 ell-Dolhard-Eelinsky 6eaction 7hen aliphatic carboxylic acid containin$ 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$ #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$ent this sulphonamide is soluble in NaO or ;O1
.) Secondary amine-7ith hinsber$ rea$entit forms sulphonamide !hich is insoluble in NaO or ;O1
*) #ertiary amine- #ertiary amine do not react !ith hinsber$ 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 ;olbes 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 $ives salicylic
acid(2-hydroxy ben5oic acid)1
%<1 6iemer-#iemann 6eaction #he reaction of pheonal !ith chloroform or carbon-tetrachloride in the presence of a>ueos alkali at +&k follo!ed by hydrolysisof the resultin$ product $ives salicyldehyde and salicylic acid respectively1
%?1 6osenmund 6eduction 6eduction of acid chloride (6*O*l)to the correspondin$ aldehyde !ith hydro$en usin$ [email protected]+ as catalyst is kno!n as rosenmund
reaction1ere [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$0 etc1
221 7illiamson/s synthesis In !illiamson synthesis!hen an alkoxide or a phenoxide is made to react !ith an alkyl halidean ether is obtained1In this methodhaloarenes can not be used for the preparation of alkyl-aryl ethers because of the lo! reactivity of aryl halides1
21 7urt5-0itti$ 6eaction #his reaction is used for obtainin$ hi$her alkane from the halo$en derivatives by usin$ sodium1
Me%a#$!m $# O0a#$% 0ea%t$o#!:
1. H2"0at$o# of A34e#e!:
*. De2"0at$o# of a3%oo3! to $5e Ete0!:
+. Rea%t$o# of ete0 6$t HI
ORGANIC REASONING 7UESTIONS
(1)o$3$# &o$#t! of am$#e! a0e 3o6e0 ta# to!e of %o00e!&o#"$# a3%oo3! o0 Ca09o23$% 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#e0 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 $roup is a donatin$ $roup)
6 → N2
7hereas in arylamines the electron cloud on nitro$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 a3oe#at$o#; o0 !'3&o#at$o#) ta4e! &3a%e o# e#<e#e 6e# e#<e#e %o#ta$#! a# e3e%t0o#$% "o#at$# 0o'&(==CH*; o0 ==OH; o0 ==NH;
o0 ==OCH*)
OR
E3e%t0o&$3$% !'9!t$t't$o# (N$t0at$o# ;o0 a3oe#at$o#; o0 !'3&o#at$o#) ta4e! &3a%e o# e#<e#e at O0to a#" Pa0a &o!$t$o#! o#32 6e# e#<e#e %o#ta$#! a# e3e%t0o#$% "o#at$# 0o'&(==CH*; o0 ==OH; o0 ==NH; o0 ==OCH*)
A#!: ,ue to the presence of an electron donatin$ $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$# $! &0e!e#t (==CHO; ==COOH; ==NO)1
A#!: ,ue to the presence of an electron !ithdra!in$ $roup on ben5ene from the resonance structures the ortho and para positions contains positive char$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 $roup1 So ketones are less reactive than aldehydes to!ards nucleophilic addition1
8. Com&a0e te a%$"$% !t0e#t! of C3=CHCOOH ; F=CHCOOH; I=CHCOOH.
A#!: F=CHCOOH C3=CHCOOH I=CHCOOH
0luorine is more electrone$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!$% !t0e#t! of te fo33o6$#. CH*NH; NH*; C-H,NH
A#!: #he basic stren$ths * N2 8 N 8 *<: N2
In * N2 * is a donatin$ $roup so the electron cloud on nitro$en increases1 * →
N21
In N nitro$en contain its o!n lone pair of electrons1
In *<: N2 *<: is an electron !ithdra!in$ $roup so electron cloud on nitro$en
decreases1 So basic stren$th decreases1
1. Fo0ma3"e2"e $5e! %a##$<a0oB! 0ea%t$o# 6e0ea! a%eta3"e2"e "oe! #ot.
A#!: 0ormaldehyde does not containα-hydro$en the compounds !hich does not containα
-hydro$en under$oes canni5aro/s reaction1
Acetaldehyde does containα-hydro$en so it does not under$o canni5aro/s reaction but it
11.Pe#23 met23 ete0 (a#$!o3e)(a023 a3423 ete0!) 0ea%t! 6$t HI to $5e Pe#o3 Met23 Io"$"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 $5e te %a0a%te0$!t$% 0ea%t$o#! of %a09o#23 0o'&.
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#! 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%$" $! a5$# $e0 >a 5a3'e ta# a%et$% 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
A?AHAR NAODAYA IDYALAYA; NIAMSAGAR.
O0a#$% %em$!t02 Date: 1*=1=1
C3a!!: II Ma. Ma04!:
I. Distinguish between the following pairs of compounds by giving a chemical test.(Any 10).10M
1) C2H5NH2 and C2H5NHC2H5 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.& alylation 7) o&en-nd reaction !) Cle-en&on redction' ") Cro&& Aldol Conden&ation 1%) Hellolhardelin&y reaction 11) Coplin+ reaction
12) Carbyl a-ine reaction 13) ie-ertie-ann reaction 14) Ho00-an broa-ide reaction
III. #ive the reasons for the following. (Any 1$) 1%M 1) Cycloheanone 0or-& cyanohydrin in +ood yield bt 226tri-ethyl
cycloheanone doe& not'
2) rin+ addition o0 a--onia deri8ati8e& to the carbonyl co-pond& PH 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+ alane' (hy: 5) Nitration o0 phenol& +i8e& only ortho and para prodct&' ,i8e rea&on'
6) Carboylic acid& do not +i8e characteri&tic reaction& o0 carbonyl +rop'(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 =NH2 +rop& in &e-icarbazide' Ho;e8er only one i& in8ol8ed in
the 0or-ation o0 &e-icarbazone&' '
1%) iazoni- &alt& o0 aro-atic a-ine& are -ore &table than tho&e o0 aliphatic a-ine&'
11) >etone& are le&& reacti8e to;ard& ncleophile& than aldehyde&'
12) Eplain the /N2 -echani&- ;ith rele8ant ea-ple 0oc&in+ on in8er&ion o0
Con0i+ration $ &teric e00ect'
13) Eplain ;hy i& oNitroPhenol -ore acidic than o#ethoyphenol:
14) Phenol i& -ore acidic than cyclo heanol'
15) ?n the 0ollo;in+ pair& o0 halo+en co-pond& ;hich ;old nder+o /N 2
reaction 0a&ter:
CH2@ CH2@ CH2CHCH2@
16) (hich acid o0 each pair &ho;n here ;old yo epect to be &tron+er $ +i8e rea&on: i) CH3CH $ CH2*CH ii) CH2*CH2CH2CH $ CH3
CH2CH*CH
17) Boilin+ point o0 carboylic acid& i& hi+her than that o0 alcohol& o0 &a-e -oleclar -a&& tho+h both are ha8in+ H hydro+en bond'
1!) Halo alane& react ;ith >CN to 0or- alyl cyanide& a& -ain prodct ;hile A+CN 0or-& i&ocyanide& a& the chie0 prodct' Eplain'
I&. 'rite the mechanisms of the following. (Any ) M
EtHH2
1) CH3CH2CH2CH2Br >CN CH3CH2CH2CH2CN
2) Hydration o0 ethene in pre&ence o0 dilte acid& to +i8e ethanol'
3) 9he dehydration o0 Ethyl alcohol in the pre&ence o0 con' /lphric Acid re<ed the 0or-ation o0 Ethene'
&. *omplete the following. (*onversions+ word problems) (% ! %M) ,%M 1) ,i8e the &trctre& o0 A and B in the 0ollo;in+ reaction&'
(-)
An or+anic co-pond DA. ha8in+ -oleclar 0or-la C2H52N react& ;ith (ith
HN2and +i8e& C2H43N2' n redction DA. +i8e& a co-pond DC. ;ith
-oleclar 0or-la C2H7N' DC. on treat-ent ;ith HN2+i8e& D. ;hich +i8e
po&iti8e ?odo0or- te&t' ?denti0y ABC and '(rite the corre&pondin+ reaction&'
) An or+anic co-pond contain& 6"'77 carbon 11'63 hydro+en and re&t
oy+en'9he -oleclar -a&& o0 the co-pond i& !6' ?t doe& not redce 9ollen&. rea+ent bt 0or-& an addition co-pond ;ith &odi- hydro+en&lphite and
+i8e po&iti8e iodo0or- te&t' n 8i+oro& oidation it +i8e& ethanoic and propanoic acid' (rite the po&&ible &trctre o0 the co-pond'
(-)
A co-pond DA. ;ith -oleclar 0or-la C5H1% +a8e a po&iti8e 24NP te&t
bt a ne+ati8e 9ollen.& rea+ent te&t' ?t ;a& oidized to carboylic acid DB. ;ith -oleclar 0or-la C3H62 ;hen treated ;ith alaline >#n4 nder 8i+oro&
condition&' /odi- &alt o0 DB. +a8e a hydrocarbion DC. on >olbe.& electrolytic redction' ?denti0y AB and C and ;rite the che-ical e<ation&'
$) Ho; ;ill yo brin+ abot 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 alyl halide:
(-)
Pri-ary alylhalide C4H"Br FA) reacted ;ith Alc'>H to +i8e co-pond DB.'
Co-pond 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-pond D. C!H1! that ;a&
di00erent 0ro- the co-pond 0or-ed ;hen nBtylbreo-ide i& reacted ;ith /odi-' ?denti0y AB C and and ;rite the che-ical e<ation&'
) Pri-ary alyl halide C4H"BrFA) reacted ;ith alcoholic >H to +i8e co-pond FB)'
Co-pond 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-pond F) C !H1! ;hich i& i00erent
0ro- the co-pond 0or-ed ;hen nbtyl bro-ide i& reacted ;ith &odi-' ,i8e the &trctral 0or-la o0 FA) and ;rite the e<ation& 0or all the reaction&'
(-)
An aro-atic co-pond DA. ha8in+ -oleclar 0or-la C6H6 react& ;ith n
d&t to +i8e an another aro-atic co-pond ;ith &i carbon ato-& in it& -olecle and thi& co-pond react& ;ith 0-in+ /lphric acid to +i8e
co-pond DB. ;hich i& 0&ed ;ith NaH to +i8e co-pond DC.' co-pond DC. react& ;ith C2 and 0or-& co-pond D. ;hich in trn& +i8e& co-pond DE.
in acidic -edi-' Co-pond DE. react& ;ith Acetyl Chloride to +i8e a co-pond D*. ;hich i& a 0a-iliar anti pyretic and anal+e&ic' edce the &trctre& o0 A B C E $ *'
%) An or+anic co-pond FA) ;ith -oleclar 0or-la C!H!0or-& an oran+ered
precipitate ;ith 24NP rea+ent and +i8e& yello; precipitate on heatin+ ;ith iodine in the pre&ence o0 &odi- hydroide' ?t neither redce& 9ollen&. or
dra&tic oidation ;ith chro-ic acid it +i8e& a carboylic acid FB) ha8in+ -oleclar 0or-la C7H62' ?denti0y the co-pond& FA) and FB) and eplain the
reaction& in8ol8ed'
(-)
?denti0y the rea+ent& ABCE $*0ro- the 0ollo;in+ or+anic con8er&ion' C6H5N2 *eGHCl A FCH3C)2 B Br 2GH2 C H2GH
NaN2G HCl
* HB*4 E
&I. 'rite the I/A* names of the following.(Any %) M 1) FH)CH2FN2) CH FCl)= CH2 = CH2 =CH 2) FCH3)3CCHClC6H4?p
3) CH*2CBrCl* 4) ClCH2C≡ CCH2Br
5) FCH3)2C6H4FC2H5) 6) FCH3)3C CH2CH2 = CHCH2CH3
7) CH3CFH)FCH3)CH2CH3 !) C6H5CH2CH2CCHFCH3)2
P0a%t$%e Pa&e0
(Or$anic chemistry)
C3a!!: II
Ma. Ma04!:
1. G$5e o#e eam&3e 6$t e'at$o# of ?'0t<=F$tt$ 0ea%t$o#. 1M . o$3$# &o$#t of a# A3"o3 $! $e0 ta# te %o00e!&o#"$# a34a#e. ?2@ 1M *. N$t0at$o# of &e#o3! $5e! o#32 o0to a#" &a0a &0o"'%t!. G$5e 0ea!o#. 1M +. Ca09o23$% a%$"! "o #ot $5e %a0a%te0$!t$% 0ea%t$o#! of %a09o#23 0o'&.?2@ 1M ,. ?2 $! Fo0m$% a%$" $! mo0e !t0o#e0 ta# A%et$% a%$"@ 1M -. G$5e o#e eam&3e 6$t e'at$o# of Gatte0ma## 0ea%t$o#. 1M
. A#$3$#e $! 6ea4e0 ta# C2%3oe23am$#e. ?2@ 1M
8. ?2 "oe! 0om$#at$o# of a#$3$#e; e5e# '#"e0 5e02 m$3" %o#"$t$o#! $5e ;*;,=
t0$90omoa#$3$#e $#!ta#ta#eo'!32. 1M
/. G$5e o#e eam&3e of ea% of te fo33o6$#:
a) Ca##$<a0oB! 0ea%t$o# 9) ?o3ff >$!#e0 Re"'%t$o# M 1. ?0$te IUPAC #ame to te fo33o6$#:
CH* C3 COOH
a) CH* = CH CH CHCOOH 9) NO
M NO
OH 11. ?0$te te fo33o6$# (G$5e e'at$o#! o#32):
a) ?$33$am!o#B! S2#te!$! 9) F0$e"e3 C0aftB! a3423at$o# M OR
?0$te te fo33o6$# (G$5e e'at$o#! o#32):
a) Ro!e#m'#" 0ea%t$o# 9) C3eme#!o# 0e"'%t$o#.
1. Ho6 6$33 2o' "$!t$#'$! 9et6ee# CH,NH a#" CH,NHCH,; 9a!e" o#
%em$%a3 te!t. G$5e e'at$o#!. M
1*. E&3a$# te fo33o6$#:
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$#:
a) e#<o$% a%$" $! !o3$" 6$3e a%et$% a%$" $! 3$'$".
9) >eto#e! a0e 3e!! 0ea%t$5e to6a0"! #'%3eo&$3e! ta# a3"e2"e!. M 1,. A%%o'#t fo0 te fo33o6$# o9!e05at$o#!:
a) O$"at$o# of To'3e#e to e#<a3"e2"e 6$t C0O*$! %a00$e" o't $# &0e!e#%e of
A%et$% a#2"0$"e.
9) Me3t$# Po$#t of a# a%$" 6$t e5e# #'m9e0 of Ca09o# atom! $! $e0 ta# to!e of $t! #e$9o'0! 6$t o"" #'m9e0 of %a09o# atom!. M 1-. E&3a$# 62 $! o=N$t0oPe#o3 mo0e a%$"$% ta# o=Meto2&e#o3@ M
1. E&3a$# 62@
a) Te "$&o3e mome#t of C3o0o9e#<e#e $! 3o6e0 ta# tat of %2%3oe23%3o0$"e@ 9) G0$#a0" 0eae#t! !o'3" 9e &0e&a0e" '#"e0 a#2"0o'! %o#"$t$o#!. M 18. &=D$%3o0o9e#<e#e a! $e0 Me3t$# Po$#t a#" So3'9$3$t2 ta# to!e of o= a#"
m= $!ome0!.D$!%'!!. M
1/. ?0$te te IUPAC #ame to te fo33o6$#:
a) (CH*)*CCHJC3C-H+I=&; 9) CHFC0C3F; %) C3CHC *M
. ?0$te te me%a#$!m of te fo33o6$# 0ea%t$o#: EtOH=HO
CH*CHCHCH0 K >CN CH*CHCHCHCN *M
1. De%0$9e te me%a#$!m 92 6$% te H2"0o23 0o'& atta%e" to a# a0omat$% 0$# $! mo0e a%$"$% ta# te H2"0o23 0o'& atta%e" to a# a3423 0o'&. Ho6 "oe! te &0e!e#%e of #$t0o 0o'& $# &e#o3 affe%t $t! a%$"$% %a0a%te0@
OR
?0$te te me%a#$!m of te 0ea%t$o# of HI 6$t Meto2meta#e. *M
. ?0$te IUPAC #ame! of te fo33o6$# %om&o'#"!.
a) 9) (CH*)+ %) CH*CH = O CH( CH*)CHCH*
*M *. Ho6 "o 2o' "$!t$#'$! P0$ma02; Se%o#"a02 a#" Te0t$a02 a3%oo3!. *M +. De!%0$9e te fo33o6$#:
a) C0o!! A3"o3 Co#"e#!at$o# M
9) ) He33=o3a0"=e3$#!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.
$iii% -uring the preparation of esters from a !arboyli! a!id and an al!ohol in
the presen!e of an a!id !atalyst' the "ater or the ester should be removed
as soon as it is formed. /
&(. Give simple !hemi!al tests to distinguish bet"een the follo"ing pairs of !ompounds.
a% A!etophenone and 0enzophenone b% henol and 0enzoi! a!id
!% 2thanal and ropanal /
&7. Write short note on #
a% Ho3mann4s 0romamide rea!tion b% Carbylamine rea!tion
!% Coupling rea!tion /
&8. Give the stru!tures of A and 0 in the follo"ing rea!tions.
,M
OR
A# o0a#$% %om&o'#" AB a5$# mo3e%'3a0 fo0m'3a CH,ON 0ea%t! 6$t ?$t HNOa#"
$5e! CH+O*N. O# 0e"'%t$o#; AB $5e! a %om&o'#" CB 6$t mo3e%'3a0 fo0m'3a CHN.
CB o# t0eatme#t 6$t HNO$5e! DB 6$% $5e &o!$t$5e Io"ofo0m te!t. I"e#t$f2 A;;C a#"
D.?0$te te %o00e!&o#"$# 0ea%t$o#!.
/. An organi! !ompound !ontains (5.776 !arbon' 11.(6 hydrogen and rest oygen.*he mole!ular mass of the !ompound is 8(. t does not redu!e *ollens4 reagent but forms an addition !ompound "ith sodium hydrogensulphite and give positive iodoform test. n
vigorous oidation it gives ethanoi! and propanoi! a!id. Write the possible stru!ture of the !ompound. 9/
OR
a) A %om&o'#" AB 6$t mo3e%'3a0 fo0m'3a C,H1O a5e a &o!$t$5e ;+=DNP te!t 9't a
#eat$5e To33e#B! 0eae#t te!t. It 6a! o$"$<e" to %a09o23$% a%$" B 6$t mo3e%'3a0 fo0m'3a C*H-O 6e# t0eate" 6$t a34a3$#e >M#O+ '#"e0 5$o0o'! %o#"$t$o#!. So"$'m !a3t of B
a5e a 2"0o%a09$o# CB o# >o39eB! e3e%t0o32t$% 0e"'%t$o#. I"e#t$f2 A; a#" C a#" 60$te te
%em$%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 C<H50r $A% rea!ted "ith Al!.=H to give
!ompound >04. Compound >04 is rea!ted "ith =0r to give >C4' "hi!h is an isomer of >A4. When >A4 is rea!ted "ith ?odium
metal' it gives !ompound >-4' C8H18 that "as di3erent from the
!ompound formed "hen n)0utylbreomide is rea!ted "ith ?odium. I"e#t$f2 A; Ca#" D; a#" 60$te te %em$%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 &/
