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primary. alcohol. excess KOH. CH 3 CH 2 CH 2 Cl. HC = CH. BrCH 2 CH 2 Br. CH 3 CH 2 CH 2 OH. PCl 5 /PCl 3 / SOCl 2 /HCl. HOCH 2 CH 2 OH. LiAlH 4 Dry ether. CH 3 CH 2 OH. Conc. H 2 SO 4. Br 2. MnO 4 - , OH -. H + , Cr 2 O 7 2- Heat, reflux. PCl 5 /PCl 3 / SOCl 2 /HCl. [O].

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Primary

primary


Primary

alcohol

excess

KOH

CH3CH2CH2Cl

HC=CH

BrCH2CH2Br

CH3CH2CH2OH

PCl5/PCl3/

SOCl2/HCl

HOCH2CH2OH

LiAlH4

Dry ether

CH3CH2OH

Conc. H2SO4

Br2

MnO4-, OH-

H+, Cr2O72-

Heat, reflux

PCl5/PCl3/

SOCl2/HCl

[O]

CH3CH2CO2H

O3/Zn, H2O

CH2==CH2

CH3CHO

CH3CO2H

H+, H2O

H2CO

Br2(aq)

HBr

NaOH

C2H5OH

Alc. KOH

BrCH2CH2OH

CH3CH2Cl

CH3CH2CN

C6H5OH

NaOH

KCN

P2O5

LiAlH4

Dry ether

Excess NH3

CH3CH2OC6H5

LiAlH4

Dry ether

Little NH3

CH3CH2CONH2

Br2

NaOH

Alkaline hydrolysis

(CH3CH2)3N

CH3CH2CH2NH2

CH3CH2NH2

Excess NH3

CH3CH2COO-

LiAlH4

Dry ether

CH3CH2CH2Cl

CH3C==N

ALKYL HALIDE AS USEFUL INTERMEDIATE


Primary

Benzene Reaction Chart

C6H5CH2CH3

Sulphonic acid

C6H5SO3H

Zn/Hg

c. HCl

C6H5COCH3

Conc. H2SO4

1,3-dinitrobenzene

C6H5CO2H Benzoic acid

CH3COCl/AlCl3

Conc. H2SO4/HNO3

60oC

MnO4- /H+

CH3Cl/AlCl3

C6H6

Nitrobenzene

C6H5CH3 Methylbenzene

conc.

H2SO4/HNO3

  • Sn, conc. HCl

  • NaOH

Cl2, light

Br2/FeBr3

C6H5CH2Cl (ChloroMethyl)benzene

Aniline

HNO2, 0oC

Alkaline

Naphthal-2-enol

C6H5Br Bromobenzene

CuBr

Aryl diazonium ion, C6H5-N=N+

H2O

Azo Dye (coupling)

Phenol

H3PO2

CuCN

CyanoBenzene

Benzene


Primary

C-acylation

HOC6H4COCH3

C6H5OCH3

4-hydroxyBenzenesulphonic acid

CH3COCl/AlCl3

CH3Br

Conc. H2SO4

O-acylation

C6H5O- Na+

C6H5OCOCH3

2-bromophenol or 4-bromophenol

NaOH

CH3COCl

Or CH3CO2H

Br2/FeBr3

C6H5OH

CH3Cl/AlCl3

Br2(aq)

2,4,6-tribromophenol

4-methylphenol

Or 2-methylphenol

Dil. HNO3

Na

Ar-N=N+

4-nitrophenol

Or 2-nitrophenol

Sodium phenoxide C6H5O- Na+ + H2

Coupling

reaction

Phenol Reaction Chart


Primary

CH2==C(CO2H)CH3

Conc. H2SO4

(CH3)2C==C(CH3)2

CH3CH(OH)CH3

O3,, Zn/H2O

Ozonolysis

CH3C(OH)(CO2H)CH3

H+, H2O

Dil. HCl

CH3C==N(CH3)

CH3

CH3C(OH)(SO3-)CH3

CH3CH==CH2

CH3C(OH)(CN)CH3

H2O

KCN, Alcohol

Conc. H2SO4

Conc. H2SO4

NaHSO3(aq)

NaBH4 or

LiAlH4 ether

CH3C(OH) CH3

NH(CH3)

CH3COCH3

CH3CH(OH)CH3

CH3NH2

HONH2

H2N-NH2

methanol

CH3C==N-OH

CH3

I2, NaOH

2,4 DNP

(CH3)2C==N-NH2

Propanone hydrazone

CH3C==N-NH-C6H3(NO2)2

CH3

CH3CO2- + CHI3

CH3Br

CH3CO2CH3

LiAlH4 ether

LiAlH4 ether

CH3CH2OH + CH3OH

CH3CH2OH

Propanone Reaction Chart


Primary

CH3CH==CH(CO2H)

CH3CH2COCl

Conc. H2SO4

CH3CH(OH)CH3

CH3CH2CH(OH)(CO2H)

H2, Pd

CH3CH2CH==N(CH3)

H+, H2O

Dil. HCl

CH3CH2CH(OH)(SO3-)

CH3CH==CH2

CH3CH2CH(OH)(CN)

Conc. H2SO4

H2O

KCN, Alcohol

Conc. H2SO4

NaHSO3(aq)

NaBH4 or

LiAlH4 ether

CH3CH2CH(OH)

NH(CH3)

CH3CH2CHO

CH3CH2CH2OH

CH3NH2

HONH2

O3,, Zn/H2O

Cr2O72-/H+

H2N-NH2

CH3CH2CH=CHCH2CH3

CH3CH2CH==N-OH

2,4 DNP

Tollens’ reagent

CH3CH2CH=N-NH2

Propanal hydrazone

CH3CH2CO2H

CH3CH2C==N-NH-C6H3(NO2)2

LiAlH4 ether

CH3OH

Conc. H2SO4

CH3CH2CO2-+ Ag

CH3CH2CO2CH3

CH3CH2OH

Tollens’ reagent Ag(NH3)2+

Propanal Reaction Chart


Primary

+ CHI3

C6H5O-

Zn/Hg

Conc. HCl

CH3CO2H

pyridine

RNH2

I2, OH-

+ Ag

OH-

H+/Cr2O72-

NH3

CH3CO2-

Pd H2

CH3COCl

CH3CO2H

H+

heat

Ag(NH3)2+

C6H6

AlCl3

CH3OH

P2O5

HO-

CH3CO2-

+ CH3OH

SOCl2/PCl5

CH3CO2 CH3

H2O

CH3COO-NH4+

Conc. H2SO4

CH3OH

Conc. H2SO4

NH3

CH3CO2H

LiAlH4

ether

NH3

C6H5O-

H2O

heat

LiAlH4

+ CH3OH

+ CH3OH

ACID DERIVATIVES REACTION CHART


Primary

CH3CONH2

CH3CO2C6H5

CH3CO2COCH3

HCO2-

CHI3

C6H5O-

CH3CONHR

Zn/Hg

Conc. HCl

CH3CO2H

pyridine

CH3 CO2H

CH3CH2NH2

RNH2

I2, OH-

CH3CO2-

+ Ag

OH-

H+/Cr2O72-

NH3

CH3CO2-

CH3CONH2

Pd H2

CH3COCl

CH3CO2H

H+

CH3CHO

heat

Ag(NH3)2+

C6H6

AlCl3

CH3OH

P2O5

HO-

CH3CO2-

+ CH3OH

CH3C=N

CH3COC6H5

SOCl2/PCl5

CH3CO2 CH3

H2O

CH3COO-NH4+

Conc. H2SO4

CH3OH

Conc. H2SO4

NH3

CH3CO2H

LiAlH4

ether

NH3

C6H5O-

H2O

heat

LiAlH4

CH3CONH2 + CH3OH

CH3CO2C6H5

CH3CH2OH + CH3OH

CH3CO2COCH3

CH3CH2 OH

ACID DERIVATIVES REACTION CHART


Primary

4-Hydroxybenzoic acid

Draw the structural formula for Dettol and the other two compounds.

Give the reagents and conditions for the 4-step synthesis of phenol from benzene.

Write the steps for the synthesis of ethoxybenzene from phenol.

2,2-dimethylpropan-1-ol reacts with conc. HCl via SN2 pathway.

Give the mechanism of the reaction.

Give the E2 mechanism for the dehydrohalogenation of 2-chloro-2,3-dimethylbutane using alcoholic KOH.

Why is a tertiary alcohol not used for synthesizing tertiary chloride?

Why?


Primary

1

2

3

DD

D

4

DD

DD

5

DD

DD

DD

6

DD

DD


Primary

7

(2)

8

9

(1) Outline a mechanism of the reaction:

(2) Draw the structures of all possible stereoisomers of the product.

10

11


Primary

A

12

A

Is A optically active? Explain.

13

A

A

14

Br2

NaOH

15

L

M

ethanol

Give the reagents required for the four-step synthesis of phenacetin, an analgesic.

16

17

Zn/Hg

c.HCl

18

Write the equation for the use of H2SO4 in making soapless detergent.

19


Primary

Suggest a chemical test to distinguish one compound from the other in each pair. Each test should include the reagent(s), the expected observation with each compound.

20

A

B

Suggest steps for the following synthesis:

21

  • C6H5CH3 3-nitrobenzoic acid

Nitrobenzene  chlorobenzene

22

Toluene when treated with iron and bromine gives 4-bromotoluene as one of the products. Outline a reasonable mechanism for the reaction.

23

Arrange these iodides in order of reactivity toward hydrolysis in aqueous acid C6H5-C(CH3)2-I, C6H11-CH(CH3)I and C6H11-C(CH3)2I. 88II7b

24

Give the mechanism for the reaction of 2-methylpropene and iodine chloride(I-Cl).

25

2-bromobutane reacts with an alcoholic solution of KCN to give an optically active product. Suggest the reaction mechanism.

26

27

Outline a mechanism of the electrophilic addition:

Draw the structures of all possible stereoisomers of the product.

Would the product rotate a beam of plane-polarized light? Explain your answer. 00I5a4%


Primary

1

Outline a synthetic route, in not more than four steps, to accomplish these conversions.

In each step, give the reagent(s), conditions and the structure of the organic product.

2

3

Outline the synthesis:

4


Primary

5

Give the reagent(s) and intermediates for these conversions:

6

7

99II7b


Primary

1

2

J

J

G

F

3

J

L

K

J

reacts with KOH in

ethanol to form P, Q.

Give these structures.

(2)


Primary

Arrange the following compounds in the order of increasing basic strength. Explain your answer.

4

Write down the structural formula for both the intermediate and the product.

5

With experimental details, explain how you would convert cyclohexanol to cyclohexene.

6

7


Primary

1.

Give the reaction mechanism for the reaction between 2-pentanone and 2,4-dintriophenylhydrazine

Give the structure of the intermediates:

2.

A.

B.

C.

3.

In the preparation of propanal from propan-1-ol, a side product N (C6H12O2) was formed. (1) Suggest how N is formed.

(2) Suggest one method to separate propanal from a mixture of propanal and N.

4.

Suggest a possible structure for J, K and L and explain briefly your deductions. J, C5H12O, which exists as a pair of enantiomers, and reacts with phosphorus(V) chloride to give hydrogen chloride. K, C6H10, on ozonolysis gives L, C6H10O2 91II9b

5.

Outline chemical tests which would allow you to distinguish between the compounds in

the following pairs. Describe what you would observe in each case.

2-methylcyclohexanone and cyclohexylethanone 91II9a

2-methylpentan-2-ol and 2-methylpentan-1-ol 4 marks

6.


Primary

7

Give the reagent(s) for each step and the structures of all intermediate compounds.

A

B

C

D

8

An incomplete reaction of an amine with ethanoic anhydride gave a liquid mixture on cooling. Briefly outline a procedure, using a separating funnel and appropriate reagent(s), to isolate the ethanoylation product. 92I5b3%

9


Primary

10

  • In an experiment, 25 g of (CH3)3COH react with 36 g of HCl to give 28 g of (CH3)3CCl.

  • Find the limiting reagent of the reaction, showing clearly your calculation.

  • Calculate the % yield of (CH3)3CCl. 96II7b6%

  • (3) Name the reaction type and outline the reaction mechanism. (use curly arrows to show movement of electron pairs)

11

6

12

7

Give the reagent(s) and brief experimental conditions for these conversions:

(1) CH3CH-O-CHCH3 CH3CH=CH2

CH3 CH3

(2) nitrobenzene  chlorobenzene

(3) toluene  benzaldehyde

(4) butanoic acid  CH3(CH2)2NH2 74II5a 14%

13

14

14


Primary

  • Give the reagent(s) for each step and the structures of all intermediate compounds.

  • C6H11-COCH3 C6H11-CH2OH

  • B. C6H5CONH2 3-nitrobenzoic acid

  • Aniline  colored dye (given reagent is: naphthalen-2-ol)

  • Cyclohexene  1,6-hexanedioic acid

15

16

17


Primary

18

19

20

20

  • 21 The reaction of 2,3-dimethylbutan-2-ol with concentrated sulphuric acid gives 2 alkenes.

    • A. Suggest possible structures for the two alkenes.05II6b 5%

    • B. Suggest how the 2 alkenes can be distinguished from each other by chemical means.

Give the structure of the major product:

22

A.

B.

D

C


Primary

23

24

Each conversion can be completed in not more than 3 steps. Give the reagent(s), conditions, and structure of the intermediate(s).

D.

A.

E.

B.

F.

C.

25


Primary

CH3O-readily removes HBr

Pure substitution product

LiAlH4

Dry ether

CN-

ethanol

Dilute acid


Primary

2-bromo-2-methylpentane

propene

CH3COCl

AlCl3

LiALH4

Dry ether

KCN

ethanol

3-nitrobenzoic acid

MnO4-

H+

4-ethylpropylbenzene


Primary

trans-2-phenyl-2-butene

2-butanol loses its optcial activity in acidic medium. Explain briefly.


Primary

Dehydration or SN1 occurs in acidic medium


Primary

This reaction is slow as the nucleophile is sterically hindered


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