Organic Low Achievers Material

8/11/2019 Organic Low Achievers Material

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ORGANIC CHEMISTRY (18M)

I.DISTINGUISH TESTS OF ORGANIC COMPOUNDS:

SL.NOName 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)


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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 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 toform 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 andchloroform an offensive smellin$ compound called carbylamine ( alkyl or

arylisocyanide) is formed1

+1 *lemmension 6eduction #he reduction of 8*9O $roup to methyl $roup (8*2) !ithamal$amated 5inc and conc1 *l is kno!n as *lemmension reduction1

:1 7olf-;ishner reaction A carbonyl compound on heatin$ hydra5ine and pottassiumhydroxide(;O)in a hi$h boilin$ polar solvent such as ethylene $lycol$ets reduced to

$ive a hydrocarbon1

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


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1 Battermann 6eaction Battermann reaction is used for obtainin$ chloroben5ene or

bromoben5ene from ben5enedia5onium chloride by treatin$ it !ith *u@*l or

*[email protected] 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 $ivesben5aldehyde 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 $ivesyello! 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 testsare

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$ent because it isnot havin$ replaceable hydro$en1

%1 offmann-.romamide 6eaction 7hen an amide is heated !ith bromine and analkali 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 ofsodium or potassium salt of lo!er fatty acids is called ;olbe/s electrolysis reaction1


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%:1 ;olbes Schmith process #his reaction $ives the method for fixation of *O2in the

ben5ene rin$1Sodium phenoxide on heatin$ that %2&-%+&* under +-? atm pressure

!ith *O$ives sodium salicylate !hich on reaction !ith dil1*l $ives salicylicacid(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

reaction1ere [email protected]+ used as ne$ative catalyst and prevent further reduction toalcohol1

%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 assaponification1In 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$0etc1


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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 ofaryl 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!:


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*. 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 ispresent 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#!: *


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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#


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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#


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Co#5e0!$o#!:


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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 chemicaltest.(Any 10).10M

1) C2H5NH2and 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& PHi& 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


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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 $ CH3CH2CH*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&lted 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

HN2 and +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


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+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 >#n4nder 8i+oro&

condition&' /odi- &alt o0 DB. +a8e a hydrocarbion DC. on >olbe.& electrolytic

redction' ?denti0y AB and C and ;rite the che-ical eH 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


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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 Br2GH2 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) ClCH2CCCH2Br

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


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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#


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,M

ORA# o0a#$% %om&o'#" AB a5$# mo3e%'3a0 fo0m'3a CH,ON 0ea%t! 6$t ?$t HNO a#"

$5e! CH+O*N. O# 0e"'%t$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 hydrogenand rest oygen.*he mole!ular mass of the !ompound is 8(. t doesnot redu!e *ollens4 reagent but forms an addition !ompound "ithsodium hydrogensulphite and give positive iodoform test. nvigorous oidation it gives ethanoi! and propanoi! a!id. Write thepossible stru!ture of the !ompound. 9/

ORa) A %om&o'#" AB 6$t mo3e%'3a0 fo0m'3a C,H1O a5e a &o!$t$5e ;+=DNP te!t 9't a

#eat$5e To33e#B! 0eae#t te!t. It 6a! o$"$

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Organic Low Achievers Material