Organic Synthesis, getting between functional groups

Question 1

How do you get from an alcohol to an aldehyde?

Answer 1

Start with a primary alcohol.
Acidified Potassium Dichromate (K2Cr2O7) with dilute Sulphuric acid (H2SO4) under reflux

Question 2

How do get from an aldehyde to an alcohol?

Answer 2

Lithium Aluminium Hydride (LiAlH4), in a Dry Ether

Question 3

How do you get from an alcohol to a Ketone?

Answer 3

Start with a secondary Alcohol.
Acidified Potassium Dichromate (K2Cr2O7) with dilute Sulphuric acid (H2SO4) under Reflux

Question 4

How do you get from a Ketone to an alcohol?

Answer 4

Lithium Aluminium Hydride (LiAlH4), in a Dry Ether

Question 5

How do you get from an alcohol to an ester?

Answer 5

Carboxylic acid, Acid catalyst and heat.
or
An acyl Chloride

Question 6

How do you get from an ester to an alcohol?

Answer 6

Dilute Acid or alcohol Reflux

Question 7

How do you get from an alcohol to an iodoalkane?

Answer 7

Reflux Red Phosphorus and I2

Question 8

How do you get from an alcohol to an alkene?

Answer 8

Conc H3PO4 - 170c

Question 9

How do you get from an alkene to an alcohol?

Answer 9

steam with a H3PO4 Catalyst.
60 - 70 atm (high Pressure).
300c

Question 10

How do you get from an alcohol to a Chloroalkane?

Answer 10

PCl5 or HCl.
20c

Question 11

How do you get from an alcohol to a Bromoalkane?

Answer 11

KBr (50% conc), H2SO4.
20c

Question 12

How do you get from a halogenoalkane to an alcohol?

Answer 12

Warm aqueous KOH Reflux. or.
Mg (dry ether), then carbonyl, then dilute acid

Question 13

How do you get from an alkene to a halogenoalkane?

Answer 13

Halogen2
20c

Question 14

How do you get from an alkene to a diol?

Answer 14

Acidified KMnO4
20c

Question 15

How do you get from an alkene to an alkane?

Answer 15

H2, Nickle catalyst
150c

Question 16

How do you get from an alkene to a halogenoalkane?

Answer 16

Hydrogen Halide at 20c

Question 17

How do you get from a halogenoalkane to an alkene?

Answer 17

KOH, Ethanol Reflux

Question 18

How do you go from an alkane to a halogenoalkane?

Answer 18

Halogen (x2)
UV light

Question 19

How do you get from a Halogenoalkane to a primary amine?

Answer 19

Excess ethanoic ammonia, Heat

Question 20

How do you get from a Halogenoalkane to a Nitrile?

Answer 20

KCN, ethanol reflux

Question 21

How do you get from a nitrile to a Carboxylic Acid?

Answer 21

Dilute HCL Reflux

Question 22

How do you get from a Halogenoalkane to a Carboxylic Acid

Answer 22

Mg, Dry Ether, then CO2, then dilute acid

Question 23

How do you get from a Primary amine to a Amine?

Answer 23

Halogenoalkane

Question 24

How do you get from a Carboxylic Acid to an Alcohol?

Answer 24

LiAlH4
Produces Primary Alcohol

Question 25

How do you get from a Carboxylic Acid to an Ester?

Answer 25

Alcohol Acid Catalyst, Heat

Question 26

How do you get from an Ester to a Carboxylic Acid?

Answer 26

Dilute Acid or alkali reflux

Question 27

How do you get from a Carboxylic Acid to an Acyl Chloride?

Answer 27

PCl5
20c

Question 28

How do you get from an Acyl Chloride to a Carboxylic Acid?

Answer 28

cold H2O

Question 29

How do you get from an Acyl Chloride to an Amide?

Answer 29

NH3, 20c - To make primary amine
primary amine, 20c - to make N-substituted amine

Question 30

How do you get from Benzene to a halobenzene?

Answer 30

Halogen2
Halogen Carrier,
20c

Question 31

How do you get from Benzene to a Phenylketone?

Answer 31

Acyl Chloride, AlCl3 catalyst, reflux

Question 32

How do you get from Benzene to Alkyl Benzen?

Answer 32

Halogenoalkane, AlCl3 Catalyst
reflux

Question 33

How do you get from Benzene to Nitrobenzene?

Answer 33

Concentrated HNO3
Concentrated H2SO4,
bellow 55c

Question 34

How do you get a phenylamine?

Answer 34

From a Nitrobenzene

Question 35

How do you get a phenylamine from a Nitrobenzene?

Answer 35

tin
Concentrated HCl,
Reflux,
then NaOH