1. R-X
1.1. Preparation:
1.1.1. Alkane: Free radical 3°>2°>1°
1.1.2. Alkene (reacting with HCL, HBR, HI, H+-OH-)
1.1.3. Alcohol (reacting with PCl5, PCl2, PBr3 or PI3, SOCl2 (thionyl chloride, darzen's rxn), Lucas reagent(an.zncl2+HCl))
2. aq. KOH
2.1. R-OH
3. alc.KOH
3.1. R=R
4. Elimination rxn (Dehydrohalogenaion:loss of H and halogen): product is alkene
5. Action with metals
5.1. 1. With Na (Wurtz rxn) R-X -Na/dry ether,𝛥 → R-R+NaX
5.2. Mg
5.2.1. R-MgX
5.2.1.1. Grignard's reagent:
5.2.1.2. 1. H+-OH-
5.2.1.3. 2. i) CO2 ii) H+ Product: RCOOH
5.2.1.4. 3. i) HCOOH (Formaldehyde) ii)H2O/H+ Product: 1°-alcohol
5.2.1.5. 4. Aldehyde, H2O/H+ Product: 2°-alcohol
5.2.1.6. 5. Ketone, H2O/H+ Product: 3°-alcohol
5.2.1.7. 6. R*-OH Product: R-H + MgX-OR*
5.2.1.8. 7. R-C-OR’+RMgX+H₂O ----> R-C-R’(OH)+Mg(OH)X
5.2.1.9. 8. KCN/R*CN, H2O/H+ Product: Aldehyde/ Ketone
6. Nucleophilic substictution rxn
6.1. 1. With aq. KOH or aq.NaOH R-X+KOH ---> R-OH+KX R-X+NaOH ---> R-OH+NaX
6.2. 2. With moist Ag2O R-X+AgOH ---> R-OH+AgX (unstable)
6.3. 3. With RONa (sodium alkoxide) (Williamson's rxn) R-X +RONa --𝛥-> R-O-R+NaX
6.4. 4. With KCN or NaCN R-X+KCN --𝛥-> R-CN+KX R-X+NaCN --𝛥-> R-CN+NaX
6.4.1. Properties of R-CN:
6.4.2. a. Complete hydrolysis or acidic hydrolysis R-CN -H2O/H+→RCOOH
6.4.3. b. Partial hydrolysis (incomplete hydrolysis R-CN -c.HCl→R-CO-NH2
6.4.4. c. Reduction of R-CN reducing agents :H2/Ni :H2/Pd :H2/Pt :LiAlH4