Organic Chemistry
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| Define Hydrogenation | addition of H2 to a multiple bond
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| Hydrogenation | alkene to alkane
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| Notes on Hydrogenation | syn addition
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| H2/Pd, Pt, or Ni | Hydrogenation
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| How does heat affect stability? | less heat = more stable
more heat = less stable
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| Syn Addition | two atoms or groups add to the same face of a double bond
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| Anti Addition | atoms or groups add to opposite faces of the double bond
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| 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
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| slowest to fastest rate of addition | HF<<HCL<HBR<HI
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| weakest acid to strongest acid HI, HF, HCL, HBR | HF<<HCL<HBR<HI
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| 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
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| Name the mechanism and any rule that applies: CH3CH2CH=CH2 + HBR <acetic acid> CH3CH2CH(BR)CH3 | Hydrohalogenation and markovnikov's rule
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| Define Hydrohalogenation | is the electrophilic addition of hydrohalic acids like hydrogen chloride or hydrogen bromide to alkenes to yield the corresponding haloalkanes
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| Hydrohalogenation | Alkene to alkyl halide
Alkyne to Alkenyl Halide
Alkyne to Geminal dihalide
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| Notes on Hydrohalogenation | Markovnikov's Rule
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| Hydrogen Halide ex: HBR, HCL | Hydrohalogenation
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| Define Dehydration | loss of water
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| Dehydration | alcohol to alkene
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| What kind of mechanism does Dehydration take place | E1-carbocation
E2-no carbocation
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| H2SO4 or H3PO4 | Dehydration
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| 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
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| Elimination 2 | alcohol to alkene
no carbocation
H2SO4 or H3PO4
PRIMARY
strong bulky base
sterically hindered
SECONDARY
strong base
sterically hindered
secondary LG
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| 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
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| SN1 | carbocation
forms enantiomers
TERTIARY
protic solvent, good NU, forms enantiomers
SECONDARY
protic solvent, good NU,
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| Very Good NU | I, HS, RS
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| Good NU | Br, OH, RO, CN, N3
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| fair NU | NH3, Cl, F, RCO2
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| Weak NU | H20, ROH
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| Very Weak NU | RCO2H
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| 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,
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| Protic Solvents examples | hydrogen bonding; acidic hydrogen; cations and anions;favor SN1
EXAMPLES
Formic acid, n-Butanol, isopropanol, ethanol, methanol, acetic acid, water
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| Primary | SN2
E2
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| Tertiary | SN1
E1
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| Secondary | all four
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| alkyl halide/AgNO3/aq. EtOH | SN1
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| Alkyl Halide/NaI/acetone | SN2
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| Alcohol/HX | SN1
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| alcohol/SOCl2 or PX3 | SN2
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| alkyl halide/H2O | E1
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| alkyl halide/KOH/heat | E2
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| alcohol/H2SO4/heat | E1
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| Dehydrohalogenation | alkyl halide to alkene
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| What kind of mechanism is Dehydrohalogenation | E2
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| Strong Base | Dehydrohalogenation of E2
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| Free Radical Addition of HBR | Alkene to Alkyl Bromide
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| Notes on Free Radical Addition | Anti-Mark
peroxides needed
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| HBR, Peroxides | Free Radical Addition of HBR
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| Hydration | Alkene to alcohol
Alkyne to ketone
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| Notes on Hydration | Markovnikov's
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| dilute H2SO4, H20 | Hydration
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| Hydroboration-oxidation | Alkene to alcohol
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| Notes on Hydroboration-oxidation | Syn addition, anti-mark
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| 1.B2H6, diglyme/2.H2O2, OH | Hydroboration-oxidation
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| Halogenation | Alkene to vicinal dihalide
alkene to vicinal halohydrin
alkyne to vicinal dihalide-trans alkene
alkyne to tetrahalide
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| Notes on Halogenation | anti addition, OH adds to more substituted Carbon
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| X2, CHCL3, or CCl4 | Halogenation
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| X2, H2O | Halogenation
alkene to vicinal halohydrin
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| Epoxidation | Alkene to epoxide (carboxylic acid)
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| Notes on Epoxidation | Syn addition
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| peroxy acid | Epoxidation
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| Ozonolysis | Alkene to aldehydes or ketones
alkyne to 2 carboxylic acids
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| Notes on Ozonolysis | Ozonide is intermediate
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| 1. O3/ 2. H2O, Zn or (CH3)2S | Ozonolysis
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| Formation of alkyl tosylate | alcohol to alkyl tosylate
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| Notes on alkyl tosylate | -OTs is leaving group
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| Tosylate chloride | Alkyl Tosylate
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| Formation of Alkyne Anion | Terminal Alkyne to Alkyne anion (conj. base)
Na, NH3
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| NaNH2, NH3 | Alkyne Anion
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| Alkylation | Alkyne anion to alkyne
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| Notes on Alkylation | Alkyne anion is LG
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| Methyl or primary alkyl halide | Alkylation
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| Formation of Alkyne | Vicinal dihalide to alkyne
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| Notes of formation of alkyne | double dehydro-halogenation
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| 1. 2NaNH2, NH3/ 2. H2O | Formation of alkyne
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| Hydrogenation of Alkynes | alkyne to alkane
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| 2H2/Pt, Pd, or Ni | Hydrogenation of Alkynes
alkyne to alkane
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| Lindlar Reduction | alkyne to cis alkene
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| Notes on Lindlar Reduction | Syn Addition
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| H2/CaCO3 | Lindlar Reduction
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| Metal Ammonia Reduction | alkyne to trans alkene
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| Notes on Metal Ammonia Reduction | free radical intermediates
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| Na or Li/NH3 | alkyne to trans alkene
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| X2 | Alkyne to vicinal dihalide-trans alkene;halogenation
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| 2X2 | Alkyne to tetrahalide/halogenation
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| HX | alkyne to alkenyl halide;hydrohalogenation
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| 2HX | Alkyne to geminal dihalide;hydrohalogenation
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| 1. H20/ 2. H2SO4, HgSO4 (HgO) | alkyne to Ketone;hydration
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| 1. O3/ 2. H2O | Alkyne to 2 Carboxylic Acids;ozonolysis
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