Alkane (O2, energy) CO2 +H20 (radical combustion

)
Alkane (X, heat, hv, UV, ROOR) Alkyl halides (radical)
Alcohol (hot conc H2SO4) Alkene, water
Alkene (O3) 2 carbonyls (ozonolysis)
Alkyne (O3) 2 COOH (ozonolysis)
Alkene (HBr, ROOR) Anti markovnikov
Alkene (Hg(OAC)
2
, water) Alcohol (oxymercuration: markovnikov, anti
addition, no RRG)
Alkene (BH3, ROOR) Alcohol (hydroboration: antimarkovnikov)
Alkene (X
2
) Vic-dihalides (anti addition)
Carbonyl (RMgX, H3O+) Alcohol
Vic-diols (H+) Carbonyl + R’ RRG (Pinacol RRG)
Ketone (alcohol) Hemiketal
Hemiketal (alcohol) Ketal (can be blocking group)
Aldehyde (alcohol) hemiacetal
Hemiacetal (alcohol) Acetal (can be blocking group)
Combination of aldehydes and/or ketones (OH-) Carbonyl + alcohol 2 C over (aldol condensation)
Methyl ketone (base, X2) Haloform + carboxylate
Ketone/aldehyde (yilide (PPh2-CR’, carbanion) Specific alkene (Wittig Rxn)
COOH (alcohol, H2SO4) Ester (fischer esterification)
a,b unsaturated Carbonyl (Nuc, acid) Keto-enol (1,4 addition)
Carbonyl types (sometimes enzymes) CO2 (decarboxylation
Acid chloride (H2O) COOH (HCl)
Acid chloride (ROH) Ester (HCl)
Acid chloride (RNH2) Amide (HCl)
Acid chloride (RCOOH) Anhydride (HCl)
Ester (H2O) COOH (ROH)
Amide (H2O) COOH (RNH2)
Anhydride (H2O) COOH (RCOOH)
Ester (alcohol) New ester (transesterification)
COOH (SOCl) Acid chloride
COOH +COOH (heat) Anhydride
Acid chloride (COOH, base) Anhydride
Acetoacetic ester (R’X, H3O or dil OH) Left part (no oxygen)
Acetoacetic ester (R’X, con OH) Right part (with ester)
2 ethyl acetates (NAOR, H3O) Acetoacetic ester
Aldehyde (amine, H+) Enamine
ketone (amine, H+) Imine
Aldehyde/ketone (hydrazine-HNNH, KOH) Carbonyl becomes alkane + water + N2 (wolff-
kishner)
Carbonyl (Zn(Hg), HCl, heat) Alkane (Clemmenson reduction)
Amine (CH3I, AgO, heat) Less substituted alkene (hofman elimination)
Amine (haloalkane) Substituted alkyl +HX
1° aromatic amine (nitrous acid) Diazonium salt (can be easily replaced)
Primary amide (Br2, NaOH, H2O) Primary amine with original R’ (Hofman RRg aka
Hofman degradation)
Alkene (H2, Pd) Syn alkene reduction
Alkyne (Na, NH3 (l)) Anti addition of H
Benzene ring (H2, Rh/C) Reduces benzene ring
Benzene (sulfonic acid) Sulfonation
Benzene (HNO3) Nitro group added
Primary alcohol (PCC) Carbonyl
Benzene (acyl, AlCl3) Acylation (friedel-crafts acylation)
Alkene (MCPBA) Three ring ether (epoxidation)
2 esters or ester + carbonyl (strong base) Make C-C bond (beta-diketone)


Related Interests