Organic Chemistry Structures of Organic Compounds

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Elimination (6)We saw above that OH - + an alkyl halide gives an alcohol (an S N 2 reaction). This is true only if COLDDILUTE OH - (KOH, NaOH) is used. If HOT CONCENTRATED (e.g., > 3M) is used, a second orderELIMINATION occurs to give an alkene.HBrHOTCONCH 2O +KOHIn this reaction, the HO - is acting as base, not a nucleophile.The attack of at the carbon is slower than the attack of the base at the HRate Law; Rate = k[RX][OH - ]; called E2 (elimination bimolecular)Bond MakingBrHHHHHRHRHRHHOH-HO-bond breakingGenerally the more carbon groups on a double bond, the more stable it is: Saytzeff’s ruleCl+ NaOHheat+Bromo-3-methylbutanemajor3 methyl butaneminorOrganometallics (7)We can completely alter the electronic distribution in a molecule by converting an alkyl halide into anorganometallic compound.
H 3 C δ + -Iδ -+ Mg → H 3 C δ- -Mg δ+ -I methylmagnesium iodideBr+ LietherLi+LiBrThese are carbanions (very strong bases and nucleophiles). This is one of the few reactions we learn inyear 1 from which C-C bonds can be formed. THIS IS AN IMPORTANT REACTION!8 Reaction of Organometallics with water (the carbanion is a strong base)δ-δ+MgBr+ H OHetherH+ HOMgBrpKa 15.5pKa ca. 50#1)9 Reaction of Organometallics with ketones or aldehydes (IMPORTANT C-C bond formationδ-δ+MgBr+RRδ+ δ-OetherRROMgBrH 3O +RROHketonealcohol10 Reaction with CO 2 (IMPORTANT C-C bond formation #2)δ-δ+MgBr+Oδ+ δ-OetherOOMgBrH 3O + O OHpH ca. 2carboxylic acidAlkenesPreparation of Alkenes
Page 1 and 2: Organic ChemistryYou will need to b
Page 3 and 4: C=C, CH,AromaticC=O, C-O, C-C, CHCa
Page 5 and 6: These combine to give a π-bondHHCC
Page 7 and 8: Your eyeH HHHH HH HHHHHWhen there a
Page 9 and 10: longest chain = 4= butane2) if same
Page 11 and 12: Therefore C=C is more reactive than
Page 13 and 14: 1. Molecular FormulaC 4 H 8 C 3 H 8
Page 15 and 16: hard to start reactions. Reactions
Page 19 and 20: 793(C 5 H 10 )4.1 AAlkyl Halides ?
Page 21 and 22: Called S N 2 “substitution nucleo
Page 23: Cl+ Ag + ClAg C + ClpptAgNuNuThis i
Page 27 and 28: These are extremely reactive almost
Page 29 and 30: HXHC +XHXX = OH, need H + as cataly
Page 31 and 32: Alcohols PreparationS N 2 of alkyl
Page 33 and 34: Reactions of AlcoholsPreparation of
Page 35 and 36: 3 o Alcoholno reaction at normal te
Page 37 and 38: ON+H 2NNH 2 NH2 +H 2Oin EtOHO+H 2NN
Page 39 and 40: (Phenyl acetic acid)1 o Alcohol + A

Organic Chemistry Structures of Organic Compounds

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