Reagent

EtONa/EtOH (small base) t-BuOk/t-BuOH (bulky base) H2SO4 or H3PO4 (H /H3O ) (strong acid + heat) NaNH2 (NH2-) (Very strong base) NaNH2/XX-Br (NH2 has higher pka than acetylene, can remove its H) H2/Pt,Pd,Ni,Rh[(C6H5)3P]3Cl Li,Na in EtNH2 or NH3 H2/ Ni2B (P-2), Pd/CaCO3/quinoline HI, HBr, HCl, HF (HX/X-) HBr in presence of peroxides (ROOR) Conc. H2SO4 (cold) Conc. H2SO4 (cold) then H2O (hot) H2SO4 or H3PO4 [H /H3O ] + H2O (warm and dilute) (1) Hg(OAc)2/THF-H2O (2) NaBH4, OH(1) Hg(O2CCF3)2/THF-R-OH (2) NaBH4, OH(1) BH3:THF (2) H2O2, OHB2H6 or BH3:THF R3B H2O2, aq. NaOH R3B CH3CO2H + Heat Cl2 or Br2 / in CCl4 (non-nucleophilic solvents) Cl2 or Br2 / in aq. Solution :CH2N N + Heat or Light [:CH2]
+ + + +

Name of Reaction
Dehydrohalogenation of alkyl halides Dehydrohalogenation of alkyl halides Acid-catalyzed dehydration of alcohols ( conc. acid for 1 , weaker for 2 ,3 ) Synthesis of alkene Synthesis of terminal alkyne H Hydrogenation of alkenes/alkynes Hydrogenation of alkynes Hydrogenation of alkynes Hydrogen Halides to Alkenes Hydrogen Halides to Alkenes Sulfuric Acid to Alkenes Alcohol from Alkyl Hydrogen Sulfates Acid-catalyzed hydration Oxymercuration-demercuration Solvomercuration-demercuration Hydroboration-Oxidation Hydroboration Oxidation and hydrolysis of alkylboranes Protonolysis of alkylboranes Bromine and chlorine to alkene Halohydrin formation (haloalcohol) Reactions with Carbenes

Type of Reaction
Elimination (Best with E2) [hydrogen on C removed] Elimination (Best with E2) [hydrogen on C removed] Elimination (1 =E2) (2 ,3 =E1)
Protinate OH group, leaves as H2O

Starting Material
Alkane Alkyl Halide (Anti coplanar T.S. preferred) Alkane Alkyl Halide (Anti coplanar T.S. preferred) Alkane with OH group Alkane or Alkene (alkanes need 2 equivalents of NH2) Terminal Alkyne Alkene or alkyne Alkyne Alkyne Alkene Alkene Alkene Alkene Alkene Alkene Alkene Alkene Alkene Alkylborane Alkylborane Alkene Alkene Alkene

Final Product
Alkene [More substituted alkene Zaitsevs Rule] Alkene [Less substituted alkene Hofmanns rule] Alkene with double bond between and carbons Alkene (with 1 eq. NH2) Alkyne (with 2 eq. NH2) Substituted Alkyne Alkane Trans-Alkene Syn-Alkene Alkane w/ H & X (racemic) Alkane w/ H bonded to C atom with fewest H atoms Alkane (alkyl hydrogen sulfate) Alkane (alcohol) Alkane (alcohol) Alkane (alcohol) Ether Alcohol (syn) Trialkylborane [syn] (boron attaches to least sub. C) Alkane (alcohol) Alkylborane with replaced substituent Alkane or cycloalkane Trans vicinal dihalide Alkane (major = halohydrin, minor = vic-dihalide) Cycloalkane

Elimination (NH2 takes H and bumps off halogen) Substitution (NH2 removes terminal H, leaves open +) Addition syn addition across double or triple bond Addition anti across triple bond Addition syn across triple bond Markovnikov Addition Anit-Markovnikov Addition Markovnikov Addition Markovnikov Addition then substitution Markovnikov Addition w/ rearrangement of Markovnikov addition w/o rearrangement Markovnikov addition w/o rearrangement ending in ether Anti-Markovnikov hydration of double bond Anti-Markovniov addition of BH3 to double bond Anti-Markovnikov addition of water to alkene Syn Substitution Anti-addition of halogen across double bond Anti-addition of halogen and OH group across double bond Addition to double bond to form cyclic ring

t-BuOK/CHCl3 or t-BuOK/CHBr3 CH2I2/Zn(Cu) in diethyl either (1) OsO4, pyridine (1) cold dilute KMnO4 (2) NaHSO3/H2O (2) OH-, H2O (1) KMnO4, OH-, + Heat (2) H3O+ (1) O3, CH2Cl2, -78 (2) Me2S Cl2 or Br2 in CCl4 (look at # of mols) HX (HI, HBr, HCl, HF) [X-] HBr/CH3COBr/alumina/CH2Cl2 HBr/peroxides [ROOR] R-C C-R R-C C-R Cl2/h Br2/h Br2/ROOR HBr/ROOR ROOR BF3/H2O NaNH2/NH3 PBr3 or SOCl2 MeSO2 (Ms-) or Ts- or CF3SO2 (Tf-) R-OH in H2SO4 NaR, NaOR (1) O3 (2) HOAc (acetic acid) (1) KMnO4, OH(2) H3O+

Dihalocarbenes (will maintain original cis/trans formation) Carbenoid addition (will maintain original cis/trans formation) Syn 1,2-Dihydroxylation Oxidative cleavage of double bond Ozonolysis Bromine and chlorine to alkyne (can
add twice depending on # of equivalents)

Addition of :CX2 (if R groups are trans, they will stay trans) Addition of CH2 group to form cycloalkane Syn addition of OH (1,2diols) Double bond cut in half (gives 1
double bond to the C and 1 single bond to O-)

Alkene or cycloalkene Alkene or cycloalkene Alkene Alkene Alkene Alkyne Alkyne Alkyne Alkyne Alkyne Alkyne Alkane or Alkene Alkane or Alkene Alkane or Alkene Alkene Alkene Alkene Alkene Alcohol Alcohol Alcohol Alcohol (Preferably Me, 1 )

Alkane or cycloalkane w/ X2 added stereospecifically Alkane or Cycloalkane Alkane syn 1,2-Diol Two alkenes w/ at least 1 double bond to O in each Two alkenes w/ double bonds to O Alkene w/ 1 mol equivalent Alkane w/ 2 mol equivalent Alkene w/ 1 mol equivalent Alkane w/ 2 mol equivalent Alkene Alkene (E) and (Z) Alkene (carboxylic acid) Alkene (carboxylic acid) Chloroalkane Bromoalkane (selective) Haloalkane Bromoalkane (AntiMarkovnikov) Polymer (normally massive) Cationic alkane chains Anionic alkane chains Alkyl halide Alkane Ether Ether

Double bond cut in half (puts an

O at the end of both new double bonds)

Addition of hydrogen halides to alkynes (watch #of mols) Addition of HBr facilitated with CH3COBr Addition of HBr in presence of peroxides Oxidative cleavage of alkynes Oxidative cleavage of alkynes Halogenation through radicals Halogenation through radicals Halogenation through radicals Addition of hydrogen bromide to alkene Radical Polymerization Acid-catalyzed polymerizations Base-catalyzed polymerizations Alkyl bromide and alkyl chloride addition Tosylates, Mesylates, and Triflates used as leaving groups Dehydration of a primary alcohol to form an ether Williamson Ether Synthesis

Anti-addition of halogen across double bond Markovnikov addition of HX across double bond Markovnikov addition of Br with good yield Anti-Markovnikov addition of HBr across double bond Cleavage at triple bond and 2 formed carboxylic acids Cleavage at triple bond and 2 formed carboxylic acids Halogen homolytically splits adds via SN1 Halogen homolytically splits adds via SN1 Bromine radicals can be initiated by peroxides Anti-Markovnikov addition of Br radical across double bond Radical is formed and chains are built that are enormous Cations are formed that act like radicals Anions are formed that act like radicals The alcohols unshared electron initiates the reaction Allows for a desired configuration at oxygen The H is removed from the oxygen and it adds an R group The H is removed from the oxygen and it adds an R group

(1) Hg(O2CCF3)2, t-BuOH (2) NaBH4, HOH2SO4/isobutylene TBSCL/TBS ROR ROR MCPBA Epoxide Epoxide H3O+ (acid) OR- (base) HBr 2 HBr (strong acid)

Alkoxymercuration-Demercuration Primary alcohol converted to t-Butyl ether (t-Butyl protecting group) Silyl ether protecting group Dialkyl ether reacting with acid to form oxonium salt Cleavage of ethers Epoxidation (syn addition of O at double bond forming C-O-C ring) Acid-catalyzed ring opening of epoxide (more sub. Carbon) Base-catalyzed ring opening of epoxide (less sub. Carbon) Anti 1, 2-Dihydroxylation (cis will be enantiomers, trans will be meso)

MCPBA/H+, H2O

Mercury adds and alcohol adds, removed an ROR left H is removed and t-Butyl group added at O H is removed and added at O, removed and left with ROR H atom is added to a lone pair on the oxygen atom Two SN1 reactions on same oxygen, O leaves as H2O An oxygen atom is added at double bond. Forms ring. H is removed from acid and H2O molecule attacks at (+) OR- attacks a C and lone pair on O pulls in an H Alkene is turned into a epoxide then anti addit. of OH

Alkene Alcohol (primary) Alcohol (primary) Ether (dialkyl-diethyl) Ether Alkene Epoxide Epoxide Alkene then Epoxide

Ether at double bond t-Butyl Ether Protected ether Oxonium Salt R-X Epoxide (cyclic ether) Diol (-OH groups add on both C from ring) RO- adds on a C and an H is added on O 1, 2-Diol