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Class Note for CHEM 3332 with Professor Bean at UH


Class Note for CHEM 3332 with Professor Bean at UH

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This 11 page Class Notes was uploaded by an elite notetaker on Friday February 6, 2015. The Class Notes belongs to a course at University of Houston taught by a professor in Fall. Since its upload, it has received 16 views.

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Date Created: 02/06/15
1664 V1 52 C h e m 3 3 3 2 CHAPTER 15 Conjugated Systems Orbital Symmetry UV Spectroscopy Types of Dienes RCHCH CHCHR RCHCH CH2 CHCHR RCHCCHR Nomenclature review alkenes diene Preparation of Conjugated diene elimination of HX from allylic halide O Nasnigm gt Stability of Conjugated Dienes Compare heats of hydrogenation 1 AHohydrog 2 3 H 2 IP dgt expeth observe 3 CH2CH CHCH2 m expect observe 4 CH2CH CHCH CH3 33239 expect observe Explanation of Stability VS CchHQ CH2CH3 Allyl Cation H20 2 CH CH2 H C Stability CH3 1 2 allyl 3 substituted allyl How does conjugation affect reactivity H Br gt CH2CH CHCH2 Br2 H3O Mechanism of addition of HBr CH2CH CHCH2 HB39 CH2 CH2 HBr 0 C CHQ ICH CHZCHQ H Br ratio of products at low temperature at high temperature HBr 40 C H Br ICH2 CHCH ICH2 H Br The process above is an example of Hate Kinetic versus Equilibrium Thermodynamic Control 13m womb I w 1 I C H3CHCH Hz 39 25JL 5 W c Hg g vCHE39CHz CH 4quot 2 quot 39 cbn chem M MD gt Km 6001229 12 moo CH3 ICHCHCHZ 8r 19 ADD CHBCH CHCHzBr 5 Allylic Bromination B Br2 low conc gt light HBr Consider allylic bromination in an asymmetric alkene H 4 Br Br lt CH2 CH CHCH3 Bro gt CH2 CH CHCH3 8N2 Displacement Reactions of Allylic Halides and Tosylates Nu A CH3CH2CH2 Br gt Nu B CH2CH CH2 Br gt A CH CH H 2Nu 3 2CL4H l Br 3 CH2C AH HCL4H Br Example CH2CH CH2Br Nu IC39IIIIIH CH30H2 H Nu H Nu C m gt IC H lt H 3 r gt The Diels Alder Reaction a 4 2 cycloaddition and a Nobel Prize winning reaction D w A gt D w Mechanism gt gt The dienophile 1 Must have at least one good electron withdrawing group to be reactive electron withdrawal by resonance IS best 0 H CH OCH CH 3 2 3 O o O 0 if C H example other dienophiles TcozCHs 2 Stereochemistry of the dienophile is maintained gt0on3 alt A 00on3 CHsOgC A b I gt c302cgtH3 3 The Endo Rule The electron withdrawing substituent of the dienophile prefers to occupy the endo position on the new ring system Y X Example a gt J A H gt C n O O bgt lEKO A O Explanation One more quotendoquot example CH3OQC I A I gt l COQCHs The Diene 1 Electron donating groups enhance reactivity but are not required Examples alkyl groups R alkoxy groups RO K CH3O 2 Conformation H H CH3 CH3 H30 H gt H CH3 3 Translating the stereochemistry of the diene to the product H CH0 a CH3 A I H l CH3 lo DielsAlder Reactions Using Unsymmetrical Reagents Two possible orientations for reagents in the transition state Example 1 D A l E 23 l D 2 Example 2 U lp E o l E Explanation Stability of imaginary intermediate that results from imaginary electron flow from donating to wrthdrawrng group or the quotpush pullquot mechanism CH3O CH30 CH3 1 lk H gt CH gt On 0 H u o 039 M OO l l O o CHsO C CH3O c C H 3 f H a H oo Unsymmetrical Example CH3 UV VIS Spectroscopy our most quotexcitingquot technique Pi molecular orbitals of CH2 CH CHCH2 CH2 CH2 W


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