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Mechanisms

Organic Chemistry

QuestionAnswer
Define Hydrogenation addition of H2 to a multiple bond
Hydrogenation alkene to alkane
Notes on Hydrogenation syn addition
H2/Pd, Pt, or Ni Hydrogenation
How does heat affect stability? less heat = more stable more heat = less stable
Syn Addition two atoms or groups add to the same face of a double bond
Anti Addition atoms or groups add to opposite faces of the double bond
Stereoselectivity a reaction in which a single starting material can give two or more stereoisomeric products but yields one of them in greater amounts than the other
slowest to fastest rate of addition HF<<HCL<HBR<HI
weakest acid to strongest acid HI, HF, HCL, HBR HF<<HCL<HBR<HI
Markovnikov's Rule when an unsymmetrically substituted alkene reacts with a hydrogen halide, the hydrogen adds to the carbon that has the greater number o fhydrogesn, and the halogen adds to the carbon having fewer hydrogens
Name the mechanism and any rule that applies: CH3CH2CH=CH2 + HBR <acetic acid> CH3CH2CH(BR)CH3 Hydrohalogenation and markovnikov's rule
Define Hydrohalogenation is the electrophilic addition of hydrohalic acids like hydrogen chloride or hydrogen bromide to alkenes to yield the corresponding haloalkanes
Hydrohalogenation Alkene to alkyl halide Alkyne to Alkenyl Halide Alkyne to Geminal dihalide
Notes on Hydrohalogenation Markovnikov's Rule
Hydrogen Halide ex: HBR, HCL Hydrohalogenation
Define Dehydration loss of water
Dehydration alcohol to alkene
What kind of mechanism does Dehydration take place E1-carbocation E2-no carbocation
H2SO4 or H3PO4 Dehydration
Elimination 1 alcohol to alkene carbocation present H2SO4 or H3PO4 TERTIARY weak NU, weak base (NH3/CH3NH2/C5H5N or pyridine), heat SECONDARY heat, weak base, weak NU, good LG, steric hindrance
Elimination 2 alcohol to alkene no carbocation H2SO4 or H3PO4 PRIMARY strong bulky base sterically hindered SECONDARY strong base sterically hindered secondary LG
SN2 nucleophillic substitution chirality present=stereochem achiral present=no stereochem PRIMARY aprotic solvent,good NU,strong/weak base, unhindered SECONDARY aprotic solvent, good NU, unhindered, inversion, backside attack), no carbocation
SN1 carbocation forms enantiomers TERTIARY protic solvent, good NU, forms enantiomers SECONDARY protic solvent, good NU,
Very Good NU I, HS, RS
Good NU Br, OH, RO, CN, N3
fair NU NH3, Cl, F, RCO2
Weak NU H20, ROH
Very Weak NU RCO2H
Aprotic Solvents examples no hydrogen bonding; no acidic hydrogen; stabilize ions; favor SN2 EXAMPLES DCM, THF, ethyl acetate, acetone, DMF, MeCN or acetonitrile, DMSN or dimethyl sulfoxide,
Protic Solvents examples hydrogen bonding; acidic hydrogen; cations and anions;favor SN1 EXAMPLES Formic acid, n-Butanol, isopropanol, ethanol, methanol, acetic acid, water
Primary SN2 E2
Tertiary SN1 E1
Secondary all four
alkyl halide/AgNO3/aq. EtOH SN1
Alkyl Halide/NaI/acetone SN2
Alcohol/HX SN1
alcohol/SOCl2 or PX3 SN2
alkyl halide/H2O E1
alkyl halide/KOH/heat E2
alcohol/H2SO4/heat E1
Dehydrohalogenation alkyl halide to alkene
What kind of mechanism is Dehydrohalogenation E2
Strong Base Dehydrohalogenation of E2
Free Radical Addition of HBR Alkene to Alkyl Bromide
Notes on Free Radical Addition Anti-Mark peroxides needed
HBR, Peroxides Free Radical Addition of HBR
Hydration Alkene to alcohol Alkyne to ketone
Notes on Hydration Markovnikov's
dilute H2SO4, H20 Hydration
Hydroboration-oxidation Alkene to alcohol
Notes on Hydroboration-oxidation Syn addition, anti-mark
1.B2H6, diglyme/2.H2O2, OH Hydroboration-oxidation
Halogenation Alkene to vicinal dihalide alkene to vicinal halohydrin alkyne to vicinal dihalide-trans alkene alkyne to tetrahalide
Notes on Halogenation anti addition, OH adds to more substituted Carbon
X2, CHCL3, or CCl4 Halogenation
X2, H2O Halogenation alkene to vicinal halohydrin
Epoxidation Alkene to epoxide (carboxylic acid)
Notes on Epoxidation Syn addition
peroxy acid Epoxidation
Ozonolysis Alkene to aldehydes or ketones alkyne to 2 carboxylic acids
Notes on Ozonolysis Ozonide is intermediate
1. O3/ 2. H2O, Zn or (CH3)2S Ozonolysis
Formation of alkyl tosylate alcohol to alkyl tosylate
Notes on alkyl tosylate -OTs is leaving group
Tosylate chloride Alkyl Tosylate
Formation of Alkyne Anion Terminal Alkyne to Alkyne anion (conj. base) Na, NH3
NaNH2, NH3 Alkyne Anion
Alkylation Alkyne anion to alkyne
Notes on Alkylation Alkyne anion is LG
Methyl or primary alkyl halide Alkylation
Formation of Alkyne Vicinal dihalide to alkyne
Notes of formation of alkyne double dehydro-halogenation
1. 2NaNH2, NH3/ 2. H2O Formation of alkyne
Hydrogenation of Alkynes alkyne to alkane
2H2/Pt, Pd, or Ni Hydrogenation of Alkynes alkyne to alkane
Lindlar Reduction alkyne to cis alkene
Notes on Lindlar Reduction Syn Addition
H2/CaCO3 Lindlar Reduction
Metal Ammonia Reduction alkyne to trans alkene
Notes on Metal Ammonia Reduction free radical intermediates
Na or Li/NH3 alkyne to trans alkene
X2 Alkyne to vicinal dihalide-trans alkene;halogenation
2X2 Alkyne to tetrahalide/halogenation
HX alkyne to alkenyl halide;hydrohalogenation
2HX Alkyne to geminal dihalide;hydrohalogenation
1. H20/ 2. H2SO4, HgSO4 (HgO) alkyne to Ketone;hydration
1. O3/ 2. H2O Alkyne to 2 Carboxylic Acids;ozonolysis
Created by: studentdee on 2011-04-30



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