L4 drug synthesis and halides

What reagents are used to convert an alcohol (R-OH) into an alkyl chloride (R-Cl)?

SOCl_2 (Thionyl chloride) or POCl_3 (Phosphorus oxychloride).

What reagents are used to convert an alcohol (R-OH) into an alkyl bromide (R-Br)?

TsCl (Tosyl chloride, to convert the -OH into a good leaving group) followed by LiBr (Lithium bromide).

What is the name of the reaction that converts an alkyl chloride (R-Cl) to an alkyl iodide (R-I), and what reagents are used?

Reaction Name: Finkelstein reaction

Reagents: KF or KI with acetone (solvent).

What type of reaction mechanism is involved in the conversion of R-Cl to R-F or R-I using an alkali metal halide?

Substitution via an SN2 reaction.

Why is fluorine (F) a poor leaving group in nucleophilic substitution?

high stability of the C–F bond.

What factor does the equilibrium of the Finkelstein reaction depend on?

The solubility of the metal salt produced in the reaction. 

Why is acetone used as a solvent in the Finkelstein reaction, and what happens to the by-product (KCl or KBr)?

Solvent Role: KCl and KBr are insoluble in acetone. 

Effect: They precipitate out, which removes them from the equilibrium to collect pure product.

What reagent is used to convert an alkyl halide (R-Hal) into an alcohol (R-OH)?

KOH

What reagent is used to convert an alkyl halide (R-Hal) into an ether (R-O-R^1)?

Na^+^-O-R^1.

What reagent is used to convert an alkyl halide (R-Hal) into an ester (R-O-C(=O)-R^1)?

R^1-CO-O^-Ag^+. 

What reagents are used to convert an alkyl halide (R-Hal) into a thiol (R-SH) or thioether (R-S-R^1)?

K^+^-SH or K^+^-SR^1. 

What reagent is used to convert an alkyl halide (R-Hal) into a nitro compound (R-NO_2)?

NaNO_2. 

What type of reagent is used to convert an alkyl halide (R-Hal) into an amine (R-N-…-)?

An amine or ammonia source (H-N-…-)

What reagent is used to convert an alkyl halide (R-Hal) into an azide (R-N_3)?

NaN_3. 

What reagent is used to convert an alkyl halide (R-Hal) into a nitrile (R-C\equiv N)?

NaCN.

Use of mercaptopurine

First effective drug treatment for leukaemia

Steps of drug synthesis of mercaptopurine

1 conversion ROH→R-Cl

2 conversion R-Cl→R-SH