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Mechanisms
Organic Chemistry
| Question | Answer |
|---|---|
| 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 |
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