organic synthesis

Question 1

how to go from alkane ->halogenoalkane?
conditions

Answer 1

free radical substitution
UV light

Question 2

how to go from alkene -> halogenoalkane?

Answer 2

electrophilic addition, Hbr, Hcl, br2/cl2

Question 3

how to go from halogenoalkane -> alkene

Answer 3

Ethanolic KOH, elimination, heat under reflux!!

Question 4

how to go from halogenoalkane -> alc

Answer 4

Ns, w aqueous NaOH, heat under reflux!!

Question 5

alcohol -> alkene

Answer 5

elimination = mechanism, also known as dehydration, conc H2SO4/conc H3PO4 OR Al2O3 catalyst
high T for acid dehydration

Question 6

alkene -> alcohol

Answer 6

H2O, conc H2SO4/H3PO4 acid catalyst, High T+P, EA

Question 7

halogenoalkane -> amine

Answer 7

XS NH3 dissolved in ethanol, NS

Question 8

halogenoalkane -> nitrile

Answer 8

KCN dissolved in ethanol, NS

Question 9

alcohol -> halogenoalkane

Answer 9

HBr/Cl/I (prepared from NaBr/Cl/I + conc H2SO4), HEAT UNDER REFLUX, substitution

Question 10

1’ alc -> aldehyde

Answer 10

acidified potassium dichromate soln, HEAT + DISTIL, oxidation

Question 11

2’ alc -> ketone

Answer 11

acidified K2Cr2O7 soln, heat under reflux, oxidation

Question 12

alde -> CA

Answer 12

acidified K2Cr2O7, heat under reflux, oxidation

Question 13

aldehyde -> 1’ alc

Answer 13

NaBH4, aq, nucleophilic addition, reduction

Question 14

ketone -> 2’ alc

Answer 14

NaBH4, aq, NA, reduction

Question 15

ald/ket -> hydroxynitrile

Answer 15

KCN followed by dilute acid, NA, addition

Question 16

CA -> ald

Answer 16

LiAlH4, IN DRY ETHER, NA, reduction

Question 17

CA -> 1’ alc

Answer 17

LiAlH4, IN DRY ETHER, NA, reduction

Question 18

CA -> ester

Answer 18

alc, conc sulphuric acid, NA-E, elimination/condensation

Question 19

nitrile -> primary amine

Answer 19

LiAlH4, IN DRY ETHER, NA, reduction
OR
reduce w H2 using Ni catalyst

Question 20

CA -> ammonium salt

Answer 20

ammonia soln, room temp!!, neutralisation
CH3COOH + NH3 → CH3COONH4

Question 21

CA -> sodium salt

Answer 21

СН3СООН + NaOH → CH3COONa
+ H20
NaOH aq/Na2CO3, room temp!!!, neutralisation

Question 22

acid chloride -> CA

Answer 22

H20, room temp, Na-e, hydrolysis

Question 23

acid chloride -> amide

Answer 23

ammonia -> concentrated!!, NAE, substitution

Question 24

acid chloride -> ester

Answer 24

alcohol, room temp, NAE, esterification/ elimination

Question 25

ester -> CA

Answer 25

dilute HCl, heat under reflux, acid hydrolysis

Question 26

ester -> salt of CA

Answer 26

NaOH soln/ any alkali, heat under reflux, base hydrolysis СН3СООС2Н5 + NaOH → CH3COONa + C2H50H

Question 27

acid anhydride -> CA

Answer 27

H20, room temp, hydrolysis

Question 28

acid anhydride -> amide

Answer 28

conc nh3, room temp (CH3CO)20 + NH3 → CH3CONH2+ 3CH3COOH

Question 29

acid anhydride -> ester

Answer 29

alc, room temp, elimination/condensation

Question 30

benzene -> nitrobenzene

Answer 30

conc nitric acid + sulphuric acid, ES, low temp to X further nitration

Question 31

nitrobenzene -> phenyl amine

Answer 31

Sn, Hcl, heat under reflux, add NaOH (AQ) to liberate amine, reduction

Question 32

benzene -> phenylethanone

Answer 32

CH3COCl/ (CH3CO)2O, AlCl3 catalyst, ES