ࡱ> _ pbjbj *vr=\r=\]" nnnnn8|6O8:"""NNNNNNN$QwTO-n#!l"##OnnCO%%%#nnN%#N%%JDTN@2~R$K&NYO0OKfU;%pULTNUnTN""!#%9#M#"""OO%L"""O####U""""""""" > 4: Chapter 3 Alkenes & Alkynes Note Outline Part II Read Chap 3 (Not Sections 11-13, 15b, 17c) and p.153-154 & 157-158: Alkene Addition Reactions Addition in alkenes, rather than substitution as in alkanes Addition of Halogens No ________________________ required as in alkanes ________________________used to test for unsaturation  C = C + Br2 Brown Polar Addition of Water (Hydration) Requires ________________________ Product is an ________________________ H+  C = C + H-OH Polar Addition of Acids (HX & H-OSO3H which is another way to write H2SO4)  C = C + HBr Addition of Hydrogen (Hydrogenation) Requires appropriate catalyst-metal such as ________________________. H2 sits on metal surface and adds to _________________of double bond. IMPORTANT- forms _______if converting from: cycloalkene to cycloalkane OR alkyne to alkene (Requires _______ catalyst, ________________, to stop at __________________)  C = C + H2 Ni, Pd, or Pt Miscellaneous Notes: If either the alkene or the reagent is _______________________________product is possible. If both are ________________________products are possible. ________________ usually forms. The one that predominates is considered to be regiospecific, and its formation follows Markovnikovs Rule. ___________ reactants can be classified as ____________________ or ____________________ Electrophile has a ___________ charge (________________________): & is ________________________ Nucleophile: has a ____________ charge (_____________________) & is ________________________ Leads to electrophilic additions to double bond site on alkenes. The electrophile ALWAYS adds first. USUALLY, the electrophile is ____ but it can be other things. Markovnikoffs Rule: Addition of Unsymetric Reagents to Unsymmetric Alkenes ____________________________part of the reagent bonds to the C ___________________  C = C C + H-OH Carbocation Stability Carbocation: ________________________ that is classified as: May be formed when double bond broken W/Markinovs rule, _____ part of reagent bonds _____, to the C ________________________, so that the ________________________ is produced. Example:  CH2 = CHCH3 + H-OH ?? Pos (H+) adds first: Possible cations: Which is more stable? Follow Markovnikov? Neg (OH-) adds 2nd Restated rule: Electro+ part adds in a way to produce/involve most stable carbocation. Conjugated alkene (diene) addition- Symmetrical - 1 mole of addition reagent Obtain ____ products in _______________portions 1 mole of addition reactant will produce ______ products, each ___________________ 2 moles of addition reactant will produce _____product ______________________________ Example w/1 mole Br2:  C = C C = C + 1Br2 C C = C C (1,4-addition) ( ( Br Br  C C C = C (1,2-addition) ( ( Br Br Carbocation Resonance of conjugated diene above: C = C C = C + 1 Br2 ( Br+ adds: Double bond resonates: 2nd Br adds to both carbocations: Overall reaction equation: Conjugated alkene (diene) addition unsymmetrical - 1 mole of addition reagent: Again obtain 2 products in equal portions H Br ( (  C = C C = C + 1 HBr C ( C C = C or CH3CHBrCH=CH2 H Br ( (  C ( C = C ( C or CH3CH=CCH2Br Carbocation Resonance of above conjugated diene: C = C C = C + 1 HBr ( H+ adds: Double bond resonates: Br- adds to both carbocations: Overall reaction equation: ***Example w/conjugated cyclodiene:  Show resonance forms for carbocation formed from the following:  Conjugated alkene (diene) addition w/ 2 moles addition reactant: Overall Equation: 1st step as above w/1 mole, then adds to 2nd double bond Oxidation w/KMnO4 Test to tell __________________________________________ Produces compound w/______________________________ If alkene, changes from purple soln to brown ppt C = C + KMnO4 + H2O ( C C + MnO2 + KOH ( ( OH OH Purple soln Brown-black ppt Ozonolysis: Oxidation of alkenes w/________________________________________________ Used to ___________________________of double bond Requires: ______ Forms aldehydes ___________, names end in _________ If only 1 aldehyde product formed, the original reactant was 1 of the following: _______________________. Product will be a dial. _________________________________________________ Overall reaction summary:  Example w/ 1-butene: Example w/2-pentene Other examples: Alkyne Additions: Similar to alkene reactions, with the following exceptions: Needs _____________________ to go to alkane. Requires____________of the addition reagent. _____________________________ followed in each of the 2 steps. May stop at alkene If ___________________________ of the addition reagent is available Forms ________________isomer, with 1 exception Exception: _________________________ Forms _________alkene Use _________________________________ to stop at ________________. ____________________________________________________ Symmetrical addition (not H2) w/o catalyst (X2): 1st step forms _____________________________________________ Stops here if _________________________ available 2nd step forms alkane If ________________________ available Symmetrical addition of H2 w/ catalyst: 1st step forms ____________________________. Stops here ___________________________________________ (DOESNT matter the number of moles of H2) 2nd step ______________________________________ ____________________ used Unsymmetrical addition: Follow Markovnikovs rule in each step. Example Equation: CH3Ca"CH + 2 HBr ! 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