Contents
Preface v
Acknowledgements vi
AboutytheyAuthors vii
Chaptery1yyyyyyyyyGeneralyOrganicyChemistry 1.1–1.78
Chaptery2yyyyyyyy Isomerism 2.1–2.80
Chaptery3yyyyyyyyyHydrocarbons 3.1–3.60
Chaptery4yyyyyyyyyAlkylyHalides,yAlcoholsyandyEthers 4.1–
4.68yChaptery5yyyyyyyyyCarbonylyCompoundsyandyAcidyDerivatives 5.1–
5.68yChaptery6yyyyyyyyyESRyAminesyandyPhenols 6.1–6.70
Chaptery7yyyyyyyyyBiomolecules 7.1–7.36
Chaptery8yyyyyyyyyOrganicyReactionyMechanismsyandyReagents 8.1–
8.76yChaptery9yyyyyyyyyPracticalyOrganicyChemistry 9.1–9.12
Chaptery10yyyyyyyNomenclature 10.1–10.20
, About the Authorsy y
AkshayyChoudhary,yayrenownedyfacultyyofyorganicychemistry,yteachesyIIT-
JEEyaspirants,yassistingythemytoyachieveytheirygoal.yManyystudentsyhaveybeenysuc
cess-yfulyunderyhisyguidanceyandyachievedytopyranksyinytheyIIT–
JEEyexam.yTheyauthoryisyaypostgraduateyinychemistryyasywellyasyJunioryResearchyF
ellowyfromyNCL,yPune.
Hisyhasykeenyinterestyinytheysubjectyandystrivesytoypresentyitytoystudentsyinyayluci
dystyleytoyhelpythemyaceytheyexamsyeffortlessly.
MandakiniyChoudhary,yspecializesyinyreactionymechanismsyandyintermediates.ySheyisyaydedi-
ycated yteacher ywithyfour yyears’ yexperience yand yisypopularyamongystudentsyfor yher yzeal yto yhelpyt
hemywithytheiryboardyexaminations.
, CHAPTER
General Organic
1 Chemistry
y
Question Bank y
LEVEL 1 y
Arrangey they itemsy iny Questionsy 1–38y iny DECREASINGy ORDERy (i.e.,y greatest,y mosty etc.
first)ywithyrespectytoytheyindicatedyproperty.
Useytheyfollowingycodeytoyindicateyyouryanswers.
1. TheyacidityyofytheyprotonsyHyinyeachyofytheyfollowingyis
O O
(i) (ii) H3 C C
C
H3 C H O CH3
O O
(iii) H3C C C
CH3yO CH2
O
(a) iy>yiiy>yiii (b)y iiy>yiiiy>yi (c)yyyiy>yiiiy>yii (d)y iiiy>yiy>yii
2. RateyofyreactionyofyHNO3/H2SO4ywithyeachyofy theyfollowingyis
(i) OCH3 (ii) CN (iii) CH3
(a)y iy>yiiy>yiii (b)y iiy>yiiiy>yi (c)yyyiy>yiiiy>yii (d)y iiiy>yiy>yii
, 1.2yyyy cHAPTeryoNe
yy
3. Reactivityytowardsyhydrolysisyusingyaqueousyacidyofytheyfollowingyis
CH3
H3 C CH3 H3 C
(i) C (ii) H3 C y Nyyy (iii) Cly
Cy CH 3 C
O
O O
(a) iy>yiiy>yiii (b)y iiiy>yiiy>yi (c)yyyiy>yiiiy>yii (d)y iiiy>yiy>yii
4. ReactivityyofytheyfollowingytowardsyreactionywithyLiAlH4yis
O O
H3 C
(i) (ii) Cly (iii) OCH3
C
O
(a) iiy>yiy>yiii (b)y iiy>yiiiy>yi (c)yyyiy>yiiiy>yii (d)y iiiy>yi>yii
5. They relativey yieldy ofy they followingy alkenyly bromidesy fromy they reactiony ofy 1,3-
butadieneywithyHBry(dark,yN2yatmosphere)yaty–15ºCyis
(i) (ii) (iii)
Br
Br Br
(a)y iy>yiiy>yiii (b)y iiy>yiiiy>yi (c)yyyiy>yiiiy>yii (d)y iiiy>yiy>yii
6. Theyamountyofyconjugateyadditionyobtainedyinytheyreactionyofytheyfollowingywithy3-
butenoneyis
(i)y CH3Li (ii)y CH3MgBr (iii) CH3O2C–yCH–CO2CH3
(a)y iy>yiiy>yiii (b)y iiy>yiiiy>yi (c)y iy>yiiiy>yii (d)y iiiy>yiy>yii
7. TheyrelativeyreactivityytowardsyBr2yinyCHCl3yofytheyfollowingyis
(i) CH2=CH–CO2CH3 (ii)y CH2=CH–CH3 (iii)y CH2=CH–O–CH3
(a)y iy>yiiy>yiii (b)y iiiy>yiiy>yi (c)yyyiy>yiiiy>yii (d)y iiiy>yiy>yii
8. They%yofytheyparayproductyproducedyinytheyreactionyofyBr2/FeBr3ywithyeachyofytheyfollowin
gyis
CH3 NO2 C(CH3)3
(i) (ii) (iii)
(a)y iy>yiiy>yiii (b)y iiy>yiiiy>yi (c)yyyiy>yiiiy>yii (d)y iiiy>yiy>yii
9. Theynumberyofyenolizableyprotonsyinyeachyofytheyfollowingyis
O
O O
(i) (ii) O (iii)
CH
H3y Cy
(a) iy>yiiy>yiii (b)y iiy>yiiiy>yi (c)yyyiy>yiiiy>yii (d)y iiiy>yiy>yii
Preface v
Acknowledgements vi
AboutytheyAuthors vii
Chaptery1yyyyyyyyyGeneralyOrganicyChemistry 1.1–1.78
Chaptery2yyyyyyyy Isomerism 2.1–2.80
Chaptery3yyyyyyyyyHydrocarbons 3.1–3.60
Chaptery4yyyyyyyyyAlkylyHalides,yAlcoholsyandyEthers 4.1–
4.68yChaptery5yyyyyyyyyCarbonylyCompoundsyandyAcidyDerivatives 5.1–
5.68yChaptery6yyyyyyyyyESRyAminesyandyPhenols 6.1–6.70
Chaptery7yyyyyyyyyBiomolecules 7.1–7.36
Chaptery8yyyyyyyyyOrganicyReactionyMechanismsyandyReagents 8.1–
8.76yChaptery9yyyyyyyyyPracticalyOrganicyChemistry 9.1–9.12
Chaptery10yyyyyyyNomenclature 10.1–10.20
, About the Authorsy y
AkshayyChoudhary,yayrenownedyfacultyyofyorganicychemistry,yteachesyIIT-
JEEyaspirants,yassistingythemytoyachieveytheirygoal.yManyystudentsyhaveybeenysuc
cess-yfulyunderyhisyguidanceyandyachievedytopyranksyinytheyIIT–
JEEyexam.yTheyauthoryisyaypostgraduateyinychemistryyasywellyasyJunioryResearchyF
ellowyfromyNCL,yPune.
Hisyhasykeenyinterestyinytheysubjectyandystrivesytoypresentyitytoystudentsyinyayluci
dystyleytoyhelpythemyaceytheyexamsyeffortlessly.
MandakiniyChoudhary,yspecializesyinyreactionymechanismsyandyintermediates.ySheyisyaydedi-
ycated yteacher ywithyfour yyears’ yexperience yand yisypopularyamongystudentsyfor yher yzeal yto yhelpyt
hemywithytheiryboardyexaminations.
, CHAPTER
General Organic
1 Chemistry
y
Question Bank y
LEVEL 1 y
Arrangey they itemsy iny Questionsy 1–38y iny DECREASINGy ORDERy (i.e.,y greatest,y mosty etc.
first)ywithyrespectytoytheyindicatedyproperty.
Useytheyfollowingycodeytoyindicateyyouryanswers.
1. TheyacidityyofytheyprotonsyHyinyeachyofytheyfollowingyis
O O
(i) (ii) H3 C C
C
H3 C H O CH3
O O
(iii) H3C C C
CH3yO CH2
O
(a) iy>yiiy>yiii (b)y iiy>yiiiy>yi (c)yyyiy>yiiiy>yii (d)y iiiy>yiy>yii
2. RateyofyreactionyofyHNO3/H2SO4ywithyeachyofy theyfollowingyis
(i) OCH3 (ii) CN (iii) CH3
(a)y iy>yiiy>yiii (b)y iiy>yiiiy>yi (c)yyyiy>yiiiy>yii (d)y iiiy>yiy>yii
, 1.2yyyy cHAPTeryoNe
yy
3. Reactivityytowardsyhydrolysisyusingyaqueousyacidyofytheyfollowingyis
CH3
H3 C CH3 H3 C
(i) C (ii) H3 C y Nyyy (iii) Cly
Cy CH 3 C
O
O O
(a) iy>yiiy>yiii (b)y iiiy>yiiy>yi (c)yyyiy>yiiiy>yii (d)y iiiy>yiy>yii
4. ReactivityyofytheyfollowingytowardsyreactionywithyLiAlH4yis
O O
H3 C
(i) (ii) Cly (iii) OCH3
C
O
(a) iiy>yiy>yiii (b)y iiy>yiiiy>yi (c)yyyiy>yiiiy>yii (d)y iiiy>yi>yii
5. They relativey yieldy ofy they followingy alkenyly bromidesy fromy they reactiony ofy 1,3-
butadieneywithyHBry(dark,yN2yatmosphere)yaty–15ºCyis
(i) (ii) (iii)
Br
Br Br
(a)y iy>yiiy>yiii (b)y iiy>yiiiy>yi (c)yyyiy>yiiiy>yii (d)y iiiy>yiy>yii
6. Theyamountyofyconjugateyadditionyobtainedyinytheyreactionyofytheyfollowingywithy3-
butenoneyis
(i)y CH3Li (ii)y CH3MgBr (iii) CH3O2C–yCH–CO2CH3
(a)y iy>yiiy>yiii (b)y iiy>yiiiy>yi (c)y iy>yiiiy>yii (d)y iiiy>yiy>yii
7. TheyrelativeyreactivityytowardsyBr2yinyCHCl3yofytheyfollowingyis
(i) CH2=CH–CO2CH3 (ii)y CH2=CH–CH3 (iii)y CH2=CH–O–CH3
(a)y iy>yiiy>yiii (b)y iiiy>yiiy>yi (c)yyyiy>yiiiy>yii (d)y iiiy>yiy>yii
8. They%yofytheyparayproductyproducedyinytheyreactionyofyBr2/FeBr3ywithyeachyofytheyfollowin
gyis
CH3 NO2 C(CH3)3
(i) (ii) (iii)
(a)y iy>yiiy>yiii (b)y iiy>yiiiy>yi (c)yyyiy>yiiiy>yii (d)y iiiy>yiy>yii
9. Theynumberyofyenolizableyprotonsyinyeachyofytheyfollowingyis
O
O O
(i) (ii) O (iii)
CH
H3y Cy
(a) iy>yiiy>yiii (b)y iiy>yiiiy>yi (c)yyyiy>yiiiy>yii (d)y iiiy>yiy>yii
