Q1/ Complete of the following reactions giving names of ...csci.tu.edu.iq/cd/images/ASAALA.pdf · 3 benzyl chloride 9 2-Chloro -2- methyl propane 4 tri phenyl carbinol 10 2,5-dinitrobenzaldehyde

م/ مجموعة أسئلة امتحانيه نهائية 8102- 8102العلوم / قسم الكيمياء/ مرحلة ثانية /كلية / جامعة تكريت /األستاذ المساعد الدكتور احمود خلف جبر الجبوري اعداد

1

Q1/ Complete of the following reactions giving names of main products: -


2

Q2/ Give the name of compounds .


3

Q3/ write the structures for each of the following compounds:

1 1-Bromo -2-propanol 6 5- methoxy -2- pentanol

2 ethylene epoxide 7 2,2-diflouro butane

3 benzyl bromide 8 2-Chloro-2-methyl propane

4 tri phenyl carbinol 9 p-nitro benzoic acid.

5 methyl phenyl ether 10 2,5-dinitrobenzaldehyde

Q5 \ Draw the structure of each of the following compounds:

1 2-Chloro-2-methylhexane 6 2,2,5-trimethyl-3-hexyne

2 2,3,4-trimethyl-2-Pentane 7 4-methyl-1-nitro-2- Pentyne

3 2,2-Di methylPentane 8 3-nitro-2-hextyne

4 4-isopropyl heptane 9 3-isopropyl octane

5 2-Pentyne 10 Methyl-3-heptyne

Q6\ 1- Draw the structure of each of the following compounds:

1 Secondary butyl chloride 7 4-methyl-1-nitro-2-octene

2 2-Iodo-3-methyl-4-nitro heptane 8 2,2,5-trimethyl-3-nitro-hexyne

3 3-ethyl-4-methyl octane 9 2- hexyne

4 3-ethyl-4-methyl heptane 10 4- methyl-2- nitro Pentane

5 2-Ethyl butane 11 3,3-Di isopropyl hexane

Q7/ Write the structural formulas for each of the following :-

1 3-methyl butane 7 3,3-dimethyl-4-ethyl nonane

2 6-bromo-3-propyl-1-hexene 8 isopropyl methyl acetylene

3 3-ethyl-2-methyl pentane 9 3-bromo-2-pentene

4 3-ethyl-4-methyl hexane 10 2-ethyl-3- heptyne

5 3-ethyl-2-methyl pentane 11 3-methyl-4-ethyl octane

Q8/ Draw the structure of each of the following compounds:

1 m-chloro toluene 7 2,5-dinitrobenzaldehyde

2 2-bromo-4-iodophenol 8 m-chloro benzoic acid

3 p-bromo phenol 9 o-xylene

4 m-dichlorobenzene 10 p- xylene

5 o-nitro aniline 11 2,4,5-tri methylphenol


4

Q9/ write the structures and names for each of the following compounds:

1 2,6-di nitro toluene 7 2-chloro-5-nitro toluene

2 2-chloro-4-nitrophenol 8 methyl phenyl ether

3 P-methyl nitrobenzene 9 meta dibromobenzene,

4 benzoic acid 10 aniline

5 tri phenyl carbinol 11 benzene sulfonic acid

6 2-chloro toluene 12 2-chloro benzoic acid

Q10/ A/ write the structures and names for each of the following compounds:

1 1-chloro -2-hydroxy propane 7 n- butyl iodide

2 ethylene epoxide 8 2-diflouro butane

3 benzyl chloride 9 2-Chloro -2- methyl propane

4 tri phenyl carbinol 10 2,5-dinitrobenzaldehyde

5 methyl phenyl ether 11 p-nitro benzoic acid acid .

6 5- methoxy -2- pentanol 12 2,4-dibromo pentane

B/Correct the following incorrect names:

1 2,4,6-tribromobenzene 3 3-hydroxynitrobenzene

2 para-methylbromobenzene 4 1,6-dichlorobenzene.

Q11/ A/ Draw the structure of each of the following compounds:

1 m-chloro toluene 5 3-nitro aniline

2 2-bromo-4-iodophenol 6 2,5-dinitrobenzaldehyde

3 p-bromo phenol 7 m-chloro benzoic acid

4 m-dichlorobenzene 8 o-xylene

B / Draw the structure of each of the following compounds:

1 2-Chloro-2-methylhexane 5 2-Pentyne

2 2,3,4-trimethyl-2-Pentane 6 2,2,5-trimethyl-3-hextyne

3 2,2-Di methylPentane 7 4-methyl-1-nitro-2- Pentyne

4 4-isopropyl heptane 8 3-nitro-2-hextyne


5

C /Draw the structure of each of the following compounds:

1 m- Bromo toluene 5 p-nitro phenol

2 2-Chloro-2-methylhexane 6 2,5-dinitrobenzylchloride

3 m-bromo aniline 7 o-Iodo benzoic acid

4 m-dibromobenzene 8 Secondary butyl chloride

Q12/ write the structures for (seven) each of the following compounds:

1 1-chloro -2-hydroxy propane 11 n- butyl iodide

2 ethylene epoxide 12 2-diflouro butane

3 benzyl chloride 13 2-Chloro -2- methyl propane

4 tri phenyl carbinol 14 2,5-dinitrobenzaldehyde

5 methyl phenyl ether 15 p-nitro benzoic acid acid

6 5- methoxy -2- pentanol 16 p-nitrotoluene (frombenzene)

7 3-methylbenzyl chloride 17 2- Butanol

8 p-bromo bromobenzene 18 Ethyl phenyl ether

9 p-chlorotoluene 19 p-flourotoluene

10 1-bromo -2-hydroxy propane 20 2,5-dihydroxybenzaldehyde

Q12/B/Write astructural formula corresponding to each of the following

1 Allyl benzene 7 2- Butanol

2 Meta nitro acetophenone 8 p-bromochlorobenzene

3 Para chlorophenol 9 benzyl chloride

4 Styrene 10 n- butyl iodide

5 2,5-dinitrobenzylchloride 11 p-xylene

6 Para flouronitrobenzene 12 m- Bromo toluene

Q14/ Show how each of the following compounds can be synthesized from benzene

1 Toluene 7 butylene epoxide

2 meta nitro benzoic acid 8 diethyl ether

3 P- bromoaniline 9 2- chlorobutane

4 2-Iodo -2-propanol 10 P- Chloroaniline

5 benzyl chloride 11 methyl phenyl ether

6 4- bromophenol 12 ethylene epoxide


6

Q15/ write equations showing how to prepare each of the from the following

from benzene and any necessary organic reagents .

1 Para flouronitrobenzene 7 Styrene

2 methyl benzene 8 para- Bromo toluene

3 2-bromo -4-nitrobenzoic acid 9 aniline

4 Para chloro acetophenone 10 benzyl chloride

5 Meta nitro acetophenone 11 ortho nitro benzoic acid

6 1-bromo-3-nitrobenzene 12 2-Chloro -2- methyl propane

Q16/ Suggest one method for preparation of five of the following compounds

using the common methods of preparation :-

1 p-nitro benzoic acid(from benzene) 5 cyclohexanol

2 ethyl chloride 6 Isopropyl benzene

3 ethylene epoxide 7 1-chloro -2-hydroxy propane

4 methyl phenyl ether 8 benzyl chloride

Q17 / Suggest one method for preparation of five of the following compound s


1 p-nitro toluene (from benzene) 5 1-chloro -2-hydroxy propane

2 methyl phenyl ether 6 benzyl chloride

3 cyclohexanol 7 ethylene epoxide

4 Isopropyl benzene 8 Ethyl chloride

Q18 / Suggest one method for preparation of five of the following compounds

using the common methods of preparation :- .

1 4-nitrobenzene (from benzene) 5 Ethyl phenyl ether

2 4-nitrobenzyl chloride 6 3-chlorotoluene

3 2- Butanol 7 ethylene epoxide

4 4-bromo chlorobenzene 8 1-bromo -2-hydroxy propane


7

Q19/Answer A or B .

A/ Compare between each of the following pairs with examples:-

1/ compare E1 and E2 reactions.

2/ compare between SN1 and SN

2 reactions.

Q20) Define of the following terms giving one example :-

1-) Elimination reaction 2) maceration – demercuration 3)Williamson synthesis

for ethers 5) Clemmenson condensation . 6) Grignard reagent 7) carbonium

ion 8) wurtiz reaction 9) Alkoxy mercuration – demecuration 10) synthesis

E.J .Corey- House .coupling .

Answer and of the following ( choose only two) .

A/ Compare between each of the following pairs with examples :-

E1 and E2 reactions.

B/ Compare between each of the following pairs with examples :-

SN and SN2 reactions.

No. bimolecular nucleophilic Elimination (E2).

1 Depend on two substances ,concentre a hydroxide ion OH and alkyl haide

molecule.

2 Rate = K[CH3 Br][ OH-]

3 The OH attack R-X alkyl haide from the side back


8

4 This mechanism is including one step (single step) .attack base on hydrogen

atom.

B

C

H

C H:B

X

X CC

E2 (bimolecular elimination

5 The second order kinetics ( E2)

6 In E2 reactions the order of reactivity of Rx is CH3X > 1º > 2º > 3º

No. unimolecular nucleophilic Elimination (E1).

1 Reaction is depending on the concentre of only one substance of alkyl halide

2 Rate = K[CH3 Br]

3 The first order kinetics. E1

4 The carben ion has a flat structure

5 The mechanism is including two steps.


9

6

B

C

H

CH:B

X

CC

X

CC

X

X CC

Carbanion

7 In E1 reactions the order of reactivity of Rx is 3º > 2º > 1º > CH3X

No. unimolecular nucleophilic Elimination (E1).

1 Reaction is depending on the concentre of only one substance of alkyl

halide

2 Rate = K[CH3 Br]

3 The first order kinetics. E1

4 The carben ion has a flat structure

5 The mechanism is including two steps.

6

B

C

H

CH:B

X

CC

X

CC

X

X CC

Carbanion

7 In E1 reactions the order of reactivity of Rx is 3º > 2º > 1º > CH3X


10

Q22/ Write steps of mechanism for three of the following reactions .

Q23\ show how each of the following compounds can be synthesized :-

1-prepared butane from Chloroethane using the wurtz synthesis ,explain why is

the wurtz synthesis not good method for preparing propane.

2- prepared butane from Chloroethane using the Cory-House synthesis. then

give the equation for the reaction of propene withGrignard reagent.

3- prepared acetylene ,then give the equations for the reactions of Ethyne with

sodium ,Tolene’s reagent .

4- Write the equation for the reactions of propyne with water in the present of

H2SO4 and HgSO4 ,Show the intermediate.

5- Write chemical equations, showing all necessary reagent for the preparation of

2-methyl propanol by each the following methods

a - Hydroboration – oxidation of the alkene .

b - Use the Grignard reagent


11

Q24 \1-give a simple test to distinguish between 2-butene and 2- methybutene.

2- Write the steps for chain mechanism for the following reactions: 1-

Chloronation of methane. What the names of the steps -2-dehydration of 2-

propanol. What the names of the reaction.

3-Write the structures for the products from reductive ozonolysis of the following

reactions: a) 1,2-di methyl cyclohexene b)3,5-di methyl-4-octene

4- Write the structures and identify all the (o1 ,

o2,

o 3 and 4

o )primary ,secondary,

tertiary and quaternary, carbons and( o1 ,

o2,

o 3 ) hydrogen’s in 2, 4,4-tri methyl

hexane and 2,2-di methylpentane

5- Give the mechanistic symbole (SN1 ,SN

2 ,E

1,E

2) that are most consistent with

each the following statements.

1-Propyl halide react with potassium hydroxide in ethanol only by this mechanism

2- When 2-methyl-2-butylchloride is treated with potassium hydroxide in water

only by this mechanism……...(SN1 ,SN

2 ,E

1,E

2) .

3- when 2-butanol is allowed to stand in ethanol containing a few drops of

sulphuric acid .

Q25 \1- using KMnO4 test to distinguish between butane and 2- methybutene.

With write the equations for the reactions.

2- Write the steps for chain mechanism for the following reactions: a-

Chloronation of Ethane. What the names of the steps , (b)- Write the steps for

mechanism dehydration of 2-propanol. What the names of the reaction.10 mark

3-Write the structures for the products from reductive ozonolysis of the following

reactions: complete the following reactions?


12

Q26/ Explain the following with suitable examples ,with the preparation of Butane

a- Grignard reagent b- The Wurtz reaction c- Corey- house synthesis

2- Describe a free- radical chain mechanism for the reaction of the methane with

chloride Cl2 .

Q27/ write the structure of the major organic product formed in reaction of 2-

pentyne with each of the following :-

1- Hydrogen Chloride HCl

2- Hydrogen bromide HBr in present of the peroxide.

3- Peroxy acetic acid

4- Dilute sulphric acid

5- Bromine liquid in tetrachloride .

Q28- 1-write the mechanism for Acid – catalyzed (H2SO4) Dehydration of tertiary

butyl alcohol.

2- write equations describing the preparation of the tertiary pentyl alcohol

Molecular formula C5H12O By for Acid – catalyzed (H2SO4) Dehydration of two

different alkanes.

Q29) Suggest sequence of reactions suitable for preparing each of the

following compounds from the indicated starting material .you may use any

necessary organic or inorganic reagent.

a- 2-butyne from calcium carbide.

b- 1-bromo butane from 1-butene.

c- Propane from methyl lithium .

d- 4-Methyl-1-pentanol from 4-Methyl-1-pentene.

e- Dimethyl acetylene from 2,2,3,3-tetrachlorobutane

Q30/ complete the following sequence of reactions suitable for preparing each

of the following compounds (A,B,C,D,E).


13

Q31/ Write the equations for the reactions of Ethyne with water in the present of

H2SO4 and HgSO4 ,Show the intermediate.

Q32/ Write two the mechanism steps of the following reactions:


14

Q33/ Answer of the following

A/ Suggest a reasonable mechanism for all the following reactions:-: (choise two)

OC6H5MgCl

C6H5 OH

H CH3

3-CH3


15

C6H5MgBrO

CH3

1- diethyl ether

2- H3O

CH3

OMgBr

CH3

OMgBr

H2O

CCHCH3(BH3)2

(CH3CH2CH2)3B2-

heat

H

H

CCHCH3

H

H(BH3)2

heat

Diborane

CCHCH3

B

H

H

HCCHCH3

B

H

H

HH

H

HH2O2

CCHCH3

H

H

H

BHCH3CH2CH2

CCHCH3

H

H

H

BCH3CH2CH2

CH2CH2CH3

H2O2

OHCCHCH3

OH

H

H

H

Q34/ Explain of the Limitation of F.C. alkylation , giving one example

Limitation of F.C. alkylation:

1- The possibility of polyalkylation.

2- Possibility of rearrangement of carbonium ion.

3- Aryl halide cannot use for alkylation.

4- Aromatic rings containing – NH2 – NHR or NR2 do not undergo F.C. alkyl

because these groups are strongly basic which read with the Lewis acid.


16

Q35/ Define of the following terms, giving one example :-

1-) Elimination reaction 2) mercuration – demecuration 3) SN1 4).

Williamson synthesis for ethers 5) Clemmenson condensation.

1) Elimination reaction

The most important of these methods of preparation alkenes .alkyl halides are

converted into alkenes by dehydrohalogenation : elimination of the elements of

hydrogen halide

C C

H X

C CKOHAlcohol

KXH2O

H3C C C

CH3

H

CH3

CH3

Cl

H3C C C

CH3

CH3

CH3

KOHAlcohol

KClH2O

mercuration – demercuration of alkene to Preparation of alcohol

4-Williamson synthesis: for preparation of symmetrical and asymmetrical

ethers, As aryl alkyl ethers as well as di alkyl ethers.


17


18

Q36) write the steps the Grignard reaction between an ethyl magnesium chloride

(C2 H5 Mg Cl) and 1) formaldehyde 2) - ethylene oxide

Q37 / Suggest a reasonable mechanism for this reaction when tert -butyl

bromide is allowed to stand in water is formed tert -butyl alcohol.

Q38) Give the product of each of the following reactions

Q39) Limitation of the Gigrand synthesis:

1-any acidic hydrogen decompose Grignard Regent any hydrogen attached to

electron negative element (oxygen, nitrogen, sulfur, or even triply bonded carbon).

2-Grignard regent reaches rapidly with atmospheric humidity, oxygen and carbon

dioxide.

3-Grignard reagent reacts with every organic compounds containing carbon-

oxygen or carbon- nitrogen multiple bond.

4-Grignard regent cannot prepared from compounds contain in additional to

halogen.

Contain certain groups such as carboxyl COOH, hydroxyl (-OH) amino (NH2) and

SO3H (All contain acidic hydrogen which decompose Grignard reagent . Another

groups such as ( C = O ), COOR, and C=N, which Grignard reagent added to it.

NO2 group oxidize Grignard reagent .


19

Also the aldehyde or ketene must not contain groups that react toward Grignard

reagent in which the Grignard reagent decomposed before it could add to the

carbonyl group ( G may not , NO2, COOH, NH2)

Q40/ when 2-phenyl-2-butanol is allowed to stand in ethanol containing a few

drops of sulphuric acid, the following ether is formed

Q41/ show how each of the following compounds can be synthesized from

benzene P- Chloroaniline 2) M-Nitrobenzoic acid 3)Ethyl benzene

CH3 NO2

HNO3 / H2SO4K2CrO7

COOH

NO2

CH2CH3 COOH

K2CrO7CH3CH2Cl

AlCl3


20

C6H5MgBrO

CH3

1- diethyl ether

2- H3O

CH3

OMgBr

CH3

OMgBr

H2O

Q42/ Suggest one method for preparation of four of the following compound


1) p-nitro Phenol (from benzene) 2) M-Nitrobenzoic acid 3) 2- Butanol

4) p-bromochlorobenzene 5) P- Chloroaniline 6) Ethyl benzene

Q43 /1/ Why the –CH3 group is ortho –para directing while Why halogenes are

ortho –para directing

Why the _CH3 group is ortho–para directing

The stability of the carbocation intermediate formed in the rate-determining

step is actually the underlying factor for a substituent to direct an incoming

electrophile to a particular position, ortho, meta or para. The methyl group

(CH3) donates electrons inductively, and in the presence of this electrondonating

group the resonance contributors formed from ortho, meta and para attacks are

shown below. In the most stable contributors, arising from ortho and para attacks,

the methyl group is attached directly to the positively charged carbon, which can

be stabilized by donation of electrons through the inductive effect. From meta

attack no such stable contributor is formed. Thus, the substitutions in ortho and

para positions are favoured. Therefore, the methyl group is an ortho and para

directing group


21

Why halogens are ortho–para directing

Halogens are the only deactivating substituents that are ortho–para directors.

However, they are the weakest of the deactivators. Halogens withdraw electrons

from the ring through the inductive effect more strongly than they donate electrons

by resonance. It is the resonance-aided electron-donating effect that causes

halogens to be ortho–para-directing groups. Halogens can stabilize the transition

states leading to reaction at the ortho and para positions.On the other hand, the

electron-withdrawing inductive effect of halogens influences the reactivity of

halobenzenes. A halogen atom, e.g. Cl, donates an unshared pair of electrons,

which give rise to relatively stable resonance structures contributing to the hybrids

for the ortho- and para substituted arenium ions. Thus, despite being deactivators,

halogens are ortho- and para-directors. The resonance contributors formed from

ortho, meta and para attacks on the chlorobenzene are shown below.


22

Q44/ Can you Give the structure of compounds A,B,C ,D and E of the following

scheme .

Q45) Compound A has a molecular formula of C5H12O and is oxidized by

an acidic of sodium dichromate to give compound B , Whose molecular formula

of C5H10O.When compound A is heated with H2SO4 , C ,D are obtained.

Considerably more D is obtained than C . Compound C reacts with O3 , followed

by treatment with H2O2 ,to give two products : formic acid and compound whose

molecular formula of C4H8O. compound D reacts with O3 followed by treatment

with H2O2 ,to give compound f whose molecular formula is C3H6O ,and

compound G , whose molecular formula is C2H4O2 .What are the structures of

compound A through G ?


23

H3C

CH

H3C

CH

OH

CH3

H2SO4

H3C

C

H3CHC CH3

H3C

CH

H3C

CH

CH2

O3 CH3COOH

OZONIDE OZONIDE

O

OH

FORMIC ACID

H

O

HHH3C

CH

H3C

H3C

C

H3C

O

H3C

C

H3C

O COOHH3C

O3 CH3COOH

A D C

G

F

F

E

H3C

CH

H3C

C

O

CH3

B

Na2C2O7H2SO4

CH

O

C2H4O2

C3H6O

C4H8O

C5H10C5H12O C5H10

C5H10O

C3H6O

Q46/ Complete the following reactions and write the structures for the products

of the following reactions:


24

FeCl3H

Cl2

Cl

HCl

chlorobenzene

chlorination

Q47/ suggest a reasonable mechanism for all the following reactions:-:

CH3

HClCH3Cl

AlCl3

AlCl3R-ClR-C l4 R

C6H6 R C6H5

R

H

C6H5

R

H

R-C l4C6H5 R RCl3 HCl

1-

2-

3-


25

For example:

Br

HBr

H

Br2

FeBr3

bromobenzene

bromination


26

Q48/ Why the _CF3 group is meta directing?

Q49/ Why halogens are ortho–para directing?


27

Q50/ Why the _CH3 group is ortho–para directing?

The mechanism OF SN2

CH3Br OH CH3OH Br


28

C2H5

C Br

H3C

H

OH

Br

C2H5

CHO

CH3

H

C2H5

CHO

CH3

H

Br

SN2

Mechanism oF elimination E1.

B

XC

H

C

H:B

X

C C

CC CC

CarbanionH

slow

H

fast

B

C

H

C H:B

X

X CC

E2 (bimolecular elimination

E2 mechanism

1- Follow second – order kinetics.

2- Are not accompanied by rearrangement.


29

B

C

H

CH:B

X

CC

X

CC

X

X CC

Carbanion

C

H

C

X

Z:

E2 , SN2

1- oxymercurtion – demecuration of alkene.


30

Mechanism of hydroboration- oxidation:-

Mechanism (addition Grignard reagents to carbonyl compounds)


31

ArSO2OR :Z R:Z ArSHO3

C C

ASrO2O:B C C H:B ArSO3

Mechanism (Oxidation of alcohols)

R C

H

R

O -CrO3H

RCHOH

2º

Cr+3

R2CHOCrO3H HOH

R

HCrO4 H

R C

R

OH

Cr+4

HCrO3

AcetoneH2O

H2O

1)

2)

RCHOH

2º

R

R2C Cr+3Cr+4RCHOH

2º

RO

R2C O3)

4)

Mechanism of converted alcohols into Epoxide

Mechanism of converted Epoxide into alkoxyalcohol


32

Mechanism of (converted Epoxide into alcohols by Grignard reagents )

Acid – catalyzed SN2 cleavage:-


33

Base– catalyzed SN2 cleavage:-

----------------------------------------------------------------------------------------------------


34


35


36


37

H

C

OH

oxidation

O

R

OH

R

RNo reaction

3o

2o

Show how each of the following compounds can be synthesized from benzene :-

1 Styrene 6 para nitro benzene

2 triChloromethylbenzene 7 para benzoic acid

3 ortho nitro benzoic acid 8 para chloro Styrene

4 4-ethyl cyclohexane 9 ortho Chloro ethyl benzene

5 aniline 10 ortho chloro benzene

CH2= CH2

H3PO4

CH2CH3

Al2O3

CH2= CH2

H2

Styrene

CH3CH2Cl

Cl2

Heat

CHCl2CCl3

Cl2

Heat

Cl2

Heat


38


39

CH2= CH2

Styrene

CH2CH3

H2

CH2CH3

20OC

75min100 min

125ocH2

KOH

CH2= CH2

CH2CH3 CHClCH3

Cl ClCl

CH2CH3

Cl2 , FeCl3 Cl2 , heat

H

H2O

CH3

CH3Cl

AlCl3

CH3

SO3 ,35oC

CH3

SO3H

H2SO4

HCl


40

H2O

NO2NH2

HClFe

nitrobenzene

conc. HNO3

conc. H2SO4

H

H2O

NO2

Show how each of the following compounds can be synthesized from benzene

1) P- Chloroaniline 2) M-Nitrobenzoic acid 3) benzyl chloride 4)Ethyl

benzene

CH3 COOH

K2Cr2O7CH3Cl

AlCl3 H2SO4

Cl

NH2

Cl

NO2

Fe

ZnCl2

ClCl2

AlCl3

H2SO4

HNO3

CH3 COOH

HNO3 / H2SO4K2CrO7

COOH

NO2H2SO4

3-nitrobenzoic acid

benzoic acid

4-chlorobenzenamine

CH3

Cl2

Heating

CH2Cl

benzyl chloride


41

Documents

Q1/ Complete of the following reactions giving names of ...csci.tu.edu.iq/cd/images/ASAALA.pdf · 3 benzyl chloride 9 2-Chloro -2- methyl propane 4 tri phenyl carbinol 10 2,5-dinitrobenzaldehyde