Chemistry

CHOHMe
+
H
1. A(C9H16)

Me

A, on ozonolysis, gives nonane-2, 8-dione. What is A and how is it formed?

2. Complete the following equation and comment.

Me Me

KMnO4 CrO3
? OH
AcOH

3. What are A to E in the following reactions?

SOCl 2
(A) C4 H10 O C 4H9 Cl (B)
H2SO4

(i) O3 HCl
(D) C3H6O 2 C4 H8 (C) C 4H 9Cl(E)
(ii) H2O2

4. Complete the following equations.

?
(i) n  C3H7 CO 2H  n  C4H9 OH


H
(ii) Me2CO  EtMgl  ? ?

HO
(iii) EtCO2Et  2MeMgI  ? 
2
?

? MnO2
(iv) CHCO 2Et CHCH 2OH ?

? ?
(v) CH3 CH2 CH2 OH   BrCH2 CH2 COCl  BrCH2 CH2CH2 OH

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
 CHEMISTRY Book Crunch

5. What reagents could you use for the following conversions?

(i) MeCO(CH2)2CO2Et  MeCHOH(CH2)2CO2Et

(ii) HO2C(CH2)4COCl  HO2C(CH2)4CH2OH

(iii) O2N(CH2)2CN  O2N(CH2)2CH2NH2

(iv) O2N(CH2)2 CH = CH2  H2N(CH2)2 CH = CH2

(v) O2N(CH2)2CH = CH2  O2N(CH2)3CH3

(vi) Me2CHCOCl  Me2CHCHO

(vii) O2N(CH2)3CHO  O2N(CH2)3CH2OH

6. Convert CICH2CH2CHO into HOCH2CHOHCHO.

7. Suggest what compounds the letters stand for in the following equations.

 i NaNH
(i) MeCOMe  CH  CH 
 ii  A  B
2

NaNH
(ii) PhCOMe  ClCH2CO2Et 
2
C

t BuOK
(iii)  ClCH2 CO2Et 
t BuO H
D

HCI
(iv) CH3 COC2H5  EtONO 
gas
E

NH OH
(v) Et 2CO  NH4 CI  NaCN 
4
F

8. Complete the following equations and give reasons for your answer.


(i) Me2C  OH CH2OH 
H
?

H
(ii) PhMeC  OH C  OH MePh 
?

9.
* *
Using MeI, MeI, NaCN, NaCN C 14 C  *
 and any other chemicals, suggest a synthesis for each of the
following.

*
(i) CH3 CO2H

*
(ii) CH3 CO2H

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Book Crunch CHEMISTRY

* *
(iii) CH3 CO2H

* *
(iv) CH3COCH3

* *
(v) CH3 CHO

10. Complete the equations and comment.

LAH
(i) CHCI2 COCI 
?

HBr —H O
(ii) HOCH2 CH2CN 
2
?

(iii) B AC 2 mech. Me3 CCH2 OAc  OH–  ?

(iv) B AL 1 mech. Me3 CCH2 OAc  OH–  ?

acetone
(v) CICH2CO 2H  NaI  ?

Br
(vi) Me2CBrCONH2 
2
NaOH
?

11. Convert:

(i) n-BuOH into n-PrNH2

(ii) Et2CHCO2H into Et2CHCHO

12. What two compounds will condense to give each product shown (after acidification)?

EtONa
(i) A  B 
 MeCOCH2 COCO 2Et

 PhCH  CN COCO 2Et

EtONa
(ii) C  D 

EtONa
(iii) E  F   PhCH  CN  COMe

13. Complete the equations :


(i) CH2  CO2Me   ?  i Na
 CH  CO2Me 
 ii  AcOH
2 3

(ii) MeCH  CO2Et  COCO2Et  ?

heat


i EtONa
(iii) MeCH2 CO2Et  ?   
 ii AcOH  MeCH CHO CO 2Et


(iv) MeCH2 CO2Et   CO2Et  
i EtONa heat
 ii  AcOH  ?  ?
2

Complete the following equations.

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
 CHEMISTRY Book Crunch

O CH 2 O
pyridine
14. (i) HOCH 2CH2OH + ? CO  CO
O CH 2 O

(ii)


H
(iii) MeCHO  HOCH2CH2SH ?

O
? ?
(iv) R2C(OH)CH 2R R 2C — CHR R2CHCHOHR

(i) HCO3H
(v) +
?
(ii) H

 i B H
(vi) CH2  CH  CH2  CH  CH2 
 
2 6
– ?
2 ii H2O2 ; OH

(vii)  CH2 8  CO2Et 2   CH2 8  CH2OH 2

?

15. Write out the order of rates of oxidation with periodic acid of the following diols, and give your reasons:
HOCH2CH2OH, MeCHOHCHOHMe, Me2COHCH2OH, Me2C(OH)C(OH)Me2. Me2COHCHOHMe.

16. Complete the following equations and comment where necessary:

NaBH 
(i) Me  C  C 3 COCH  CH2 
4 H
 ? ?

O
Al 2O 3
(ii) CH 2 — CH2 + HCN ? ?
300°C

aq. Ca OH 2  
(iii) CH2  CHCI  CI2  ? Heat



H SO —H O
(iv) CH2  CHCN  EtOH 
2 4 2
?

NaOCI
(v) CH2  CHCOCH3 
?

Pd — C
(vi) MeCH  CHCOMe 
H 1atm 
?
2

Ni; H
(vii) MeCH  CHCOEt  2
Press.
?

(viii) MeCH = CHCO2Et + HCN ?

EtONa
(ix) CH2  CHCO2Et  EtOH 
?

H O : OH–
(x) CH2  CHCOMe 
2 2
?

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Book Crunch CHEMISTRY


(xi) CH  CNa  CI  CH2  I 
liq.
NH
i NaCN
 ? 
  
?
3 3 ii H

(xii) MeCH  CHCOMe  NH3  ?

?
(xiii) MeCH  CHCH2 CI  ?  MeCH  CHCH2I

EtONa
(xiv) MeCH  CHCO 2Et  CH3NO 2 
?

–
(xv) OH
MeCH  CHCHO  HCN  ?

(xvi) LAH
MeCH  CHCHO  ?

pyridine
(xvii) PhCHO  ?   PhCH  CHCO2H

(xviii) EtCHO  2CH2  CO2Et 2 

piperidine
?

(xix) EtCHO  CH2  CO2H2  ?

pyridine

NaOCl/NaOH HCI
(xx) EtCH  CHCH2CONH2 
 ? 
?

HO

(xxi) NH 2 + CH 2 == CO

17. Complete the following equations :

H SO
(i) CH2  CHCN  PhCH2 OH 
2 4
?

(ii) PhCH2 COCHN2  HCI  g  

Et O
2
?

heat
(iii) NH2CONH2  n  BuOH  ?

(iv) MeNH2  ?  MeNHCO2Et

aq. HBr
(v) HOCH2CH2CN 
heat
?

CH 2 +
NMe2
– Heat
(vi) O ?

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
 CHEMISTRY Book Crunch

(vii) PhCH  CN CH  CN CO2Et 

aq. HCI
heat
?

+
Et 3N H
N + CICO 2Et ? ?
(viii)

+
H
N + CH2== CHCN ? ?
(ix) warm

HCI
(x) Me 2 CHNO2  HCHO  EtNH2  ?

18. Complete the following equation:

Me 2 C  CN  NHNHC  CN  Me2  ?

HOCI
(i)

HgO
(ii) MeNHNHMe  ?

(iii) Me  CH2 2 Me 

HNO
3
500C
?

BH CINH
(iv) RCH  CH2 
2 6
 ? 
2
?

(v) Me3N  D  EtMeCHCI  ?

HO —CO
PhNCO
(vi) PhNCO 
2
 ? 
2
 ?  ?


(vii) CH2  CO 2Et  
i EtONa
 ii BrCN  ?
2

KOH
(viii) EtNH2  KCN  Br2  ?

19. Complete the following equations :

(i) R2CO  Ph3P  NH  ?

(ii) Ph3 CCI  RNH2  ?

KHCO
(iii) EtNO2  2CH2O 
3
?

(iv) RCH2NH2  2CH2 O  2HCO2H  ?

CH  CO
(v) CH2  CO  HCN  ? 
2
?

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Book Crunch CHEMISTRY

EtONa HNO
(vi) Me2C  CHCOMe  RCH2NH2  ? 
2
 ?  ?

(vii) EtCHO  CH2N2  ?

(viii) MeCOEt  CH2N2  ?


MeBr Me 2CO
(ix) ?  Et 3 N— CH2–  ?

Me

TsOH
O+ ?
(x)
N
H

(xi) CH2  CHCOMe  CH2N2  ?

20. Complete the following equations and comment where necessary :

(i) Et O
(i) n  C4H9MgBr  ? 
2
  n  C7H15 OH
(ii) H

(i) Et O
(ii) 3EtMgBr  EtO 2 CO  2
(ii) aq. NH CI
?
4

 i  Et O
(iii) PhMgBr  MeOCH2CN 
2
 ?
(ii) H

Et O
(iv) C6H11MgBr  BrCH2CBr  CH2 
2
?

 i  Et O
(v) CH2  CO  EtMgBr  2
  
?
ii H

O
(i) Et 2O
(vi) MeCH — CH 2 + Me2CHMgBr +
?
(ii) H


i EtMgBr  CuBr
(vii) EtCH  CHCOEt 
  
?
ii H

 i C H
(viii) Pr MgBr  MeC  OMe 3 6 6
  
?
ii H

 i  Et O
(ix) CICH2CO2Et  2RMgX  2
  
?
ii H

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
 CHEMISTRY Book Crunch

O
(i) Et2O
(x) MeCH — CH 2 + EtMgBr +
?
(ii) H

 i  2MeONH
(xi)  CH2  Br2 
2Mg
Et O
 ? 
  
2
?
5 2 ii H

 i Et O
(xii) MeCOCH2CO2Et  Me2Cd  2
  

ii H

 i  Et O
(xiii) Et 2Cd  CCI3CHO  2
  
?
ii H

21. Complete the following equations :

(i) 4PhLi   CH2  CH Sn  ?

4

(ii) 2EtNa + Hg ?

HO
(iii) BuLi  MeONH2  ? 
2
?

 i  CO
(iv) Me2CHLi  C2H4  ? 
 ii  H O  ?
2

(v) Me3CCI + Me2Zn ?

(vi) 2EtI + Na2/Hg ?

(vii) Et2Hg + 2K ?

(viii) 4RMgCI + SnCI4 ?

(ix) Me2Hg + Zn ?

(x) 2CH2(CN)COCI + Et2Cd ?

heat
(xi) 3Ph2Hg  2AI  ?

Me SnH
(xii) CH2  CHCOMe 
2 2
?

i Zn 
(xiii) R 2 CO  BrCH2 CH  CHCO2Et 
  

?
ii H

PbCI
(xiv) EtMgX 
2
?

(xv) PhCH2  Sn 

heat
?
4

(xvi) 2Mel  Zn / Cu  ?

(xvii) EtLi  Br2  ?

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Book Crunch CHEMISTRY

22. Complete the following equations:

O
SeO 2
(i) ?

O
EtONa
(ii) + HCO 2Et ?

NaOH
(iii) ClCH2CH2CH2CN

Zn—Cu
(iv) PhCHBrCH2CH2Br ?

Me
CrO3—H 2SO4
(v) ?
warm
OH

EtONa
(vi) C3H7CHClCOCH2Me ?
EtONa
(vii) MeCH(CH2CO2Et)CH2CH2CO2Et ?
EtONa
(viii) MeCO(CH2)3CO2Et ?
O
+
HN 3 H HN 3
(ix) + ? ? + ?
H H

CH 2CO 2H

N H 3 — H2 O +
2SOCl 2 2CH 2N 2 H Ca salt
(x) ? ? ? ? ?
Ag2O heat

CH 2CO 2H

O
Me
PhCHO LAH O3
(xi) – ? AlCl3
? ?
OH

23. Discuss

OH H+
(i) a cyclohexanone derivative
CPh2OH

OH H+
(ii) a cyclopentane derivative + a cyclohexanone derivative
C(OH)Me2

OH OH
+
(iii) H a spiro-octanone

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
 CHEMISTRY Book Crunch

24. Complete the equations

(i) + ?
CO2Me

H OAc
(ii) + ?
HO2C H

H NO2
(iii) + 100°C ?
H Ph

25. Complete the following equations.

Me Cl2 ?
CHO
(i) ?
heat
Cl Cl

Cu
(ii) 2Ph2CCl2 
PhH
?

Cl
(iii) Mg (i) CH3CHO
Et2O
? ?
(ii) aq.NH4Cl
Br

Me Fe
(iv) + Br2 ?
Me

(v) Cl Me + NaSH ?

h
(vi) PhCH3  CBrCl3  ?
(not ring substitution)

(vii) + HN ?

NaNH EtCOCHMe Na   
(viii) PhBr 
liq.NH
2
 ?  ?
3

OMe
NO2
KOH/EtOH
(ix) ?
heat

NO2

NO2
–
(i) OH ; (ii) K3Fe(CN)6
(x) ?
heat
NO2

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Book Crunch CHEMISTRY

Br
Me OMe KNH2
(xi) ?
liq.NH3

Cl Mg
(xii) ?
Et2O
Br

(xiii) + ?

26. Complete and comment.

Ph Ph

PhCHCl2  t-BuOK

 ?  ? 
 PhC  CPh t-BuOK HBr ?
 

Ph OEt

27. Complete the equations :

Me
Br EtOH-H2O
(i) + KCN ?
Heat

CH == CHCHO
Ac2O
(ii) + HNO3 ?
AcOH

CHO

(iii) HNO3
?
OMe
OMe

Cl
NO2 DMF
(iv) + NaI ?

NO2

Me
NO2 NH3
(v) ?
EtOH
NO2

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
 CHEMISTRY Book Crunch

Me EtONa
(vi) + (CO2Et)2 ?
NO2

(vii) Br NO + Cl NH2 ?

NO2
Me
(viii) + PhNO ?
O2N NO2

28. Complete the equations :

AcOH
(i) Br NH2 + NaNCO ?

Et2O
(ii) PhNH2 + ? PhNHCOCH== CHCO2H

(iii) Me NHAc + Br2 ?

AcOH
(iv) O2N NH2 + 2ICl ?

Me
HCl
(v) + NaNO2 ?
NHMe

(vi) PhCH2NH2  ?  PhCH2NHCO2Et

AcOEt
(vii) O2N NH2 + ? O2N NHCOCl
heat

HCl – AcOH
(viii) EtO NH2HCl + NH2CONH2 ?
heat

NH2
Ac2O H2SO4 HNO3 steam
(ix) ? ? ? ?
distil

(x) Ph2NH Li PhI

? ?
CuI

Cl
NO2 heat
(xi) + 2NH3 ?
press
Cl

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Book Crunch CHEMISTRY

(xii) Ph3N  MeI  ?

COMe
M.A Zn – Hg
(xiii) ? ?
HCl

+ –
NMe3 Cl
(xiv) heat
?
Me Me

?
(xv) Br CONH2 Br NH2

CO2H NH2
?
(xvi) + N2 + CO2
Cl Cl


Me2SO 4 H3O
(xvii) PhNH2  PhSO 2Cl  ? 
NaOH
 ?  ?

(xviii) PhNH2CH2CHMe 2 Br – 

heat
?

LAH NaBH
(xix) ?  PhNO2 
Pd–C
4
?

29. Complete the following equations:

NH2

(i) NO2 NaNO 2 EtOH

? ?
NO2 HCl
OMe

HCl
(ii) PhN NNHPh + PhOH ?

HCl
(iii) EtO NHNH ?

HCl
(iv) NHNH Br ?

HCl
(v) Et NHNH Et ?

HCl
(vi) EtO NHNH Me ?

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
 CHEMISTRY Book Crunch

HCl
(vii) NHNH SO3H ?

2
R
1
R
HCl
(viii) NHNH ?
EtOH

(I) + (II), where (I): R1 = R2 = OMe; (II): R1 = R2 = OEt

(ix) PhNO + Me NH2 ?

heat
(x) PhN2  BF4 –  PhNO2  ?

(xi) p – R1C 6H 4N = NC 6H4R2 — p MeCO 3H ?

OH
– + –
ArN+2 Cl ArN2 Cl
(xii) ? – + ?
OH H

NH 2

2+
– Cu
(xiii) p – ClC6H4N2+ Cl + CH 2 = CHCHO ?

30. Complete the equations:

co nc. H Cl
(i) HO NO 2 + CH2(OEt) 2 H2 
S O4
?

O
OH N a OH
(ii)  ?    CO
OH
O

heat NaCl
(iii) PhOH  (AcO)2 Hg   ? 
HO
?
2

Me
HCl
(iv)  NaNO2  ?
HO
CHMe 2

NaOH
(v) PhOH  ClCH2CO2H 
heat
?

OMe
OCH 2CH = CH 2 PhH
(vi)   ?
h ea t

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Book Crunch CHEMISTRY

CHO
OH H 2O2; aq. NaOH
(vii) ?
OMe heat

PbO Br
(viii) 2, 4, 6-tri-t-butylphenol 
2
? 
2
?
C6H6

K CO
(ix) PhOH  CH2  CHCH2Br 
2 3
?

OCHEtCH=CH 2
Me CO2 Me
(x) heat
?

OH OH
H2 SO4
(xi) + ?

CMe3

OH
NO2
(xii)  PCl5  ?

NO2

OMe
NO 2 EtOH
(xiii)  KOH 
heat
?

NO2

Me OH
H 2SO 4
(xiv) 
aq. MeOH
?
Me
O

aq. HCl
(xv)  2CH2 (CN)CO2Et  ? 
boil
?

  

Aakash Educational Services Limited - Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456