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by: Michelle Gulgowski DVM


Marketplace > University of Kentucky > Chemistry > CHE 232 > ORGANIC CHEMISTRY II
Michelle Gulgowski DVM
GPA 3.91


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Class Notes
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This 2 page Class Notes was uploaded by Michelle Gulgowski DVM on Friday October 23, 2015. The Class Notes belongs to CHE 232 at University of Kentucky taught by Staff in Fall. Since its upload, it has received 8 views. For similar materials see /class/228303/che-232-university-of-kentucky in Chemistry at University of Kentucky.

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Date Created: 10/23/15
H N Chapter 16 Dienes Allenes 12 Dienes a orbitals of two 339 bonds are orthogonal don t overlap b 0 13 disubstituted allenes are chiral chemically the two 339 bonds don t in uence each other too much 13 Dienes a O v conjugation i two contiguous 339 bonds interact with one another ii four orbitals two TE two 75 or four p orbitals make four new MOs a can be represented as l and where orbitals of the same arithmetic sign overlap constructively and those of opposite arithmetic sign overlap destructively b called 073 c have 0 3 nodes in order of increasing energy iii only mo and wl are occupied iv energy gap between HOMO and LUMO of 13 diene is smaller than in alkenes so 13 dienes absorb lower energy wavelengths v carried to more conjugated polyenes eventually absorbance occurs in visible range beta carotene conformation i in wo there is a bonding interaction between p orbitals on C2 and C3 of the 13 diene ii rotation about this 0 bond causes this interaction to go away at the 90 dihedral angle mark iii we would predict that rotation about the central bond costs energy it does but not a lot only about 4 5 kcalmol iv the two planar forms are called s cis and s trans not cis and trans which are reserved for configurational stereochemistry about rings and 339 bonds v s trans is lower in energy than s cis by about 2 3 kcalmol due to steric interaction between H atoms on C1 and C4 electrophilic addition reactions i 13 dienes undergo typical electrophilic addition reactions of alkenes ii electrophile always adds to terminal C to form allylic carbocation iii nucleophile can add to carbocation at either allylic position to give 12 or 14 addition product iv addition to terminal C gives more substituted alkene so is favored thermodynamically under conditions where products are in equilibrium with one another via cation v turns out addition to internal C is favored kinetically because nucleophile is closer to internal C after electrophile reacts with terminal C d Diels Alder reaction i 13 dienes react with alkenes to give cyclohexenes ii 39 is 1 42 JJquotinn just like carbene addition to alkenes is conceited 12 cycloaddition iii 13 diene must be s cis a higher energy conformation is required b 13 dienes locked into s cis conformation react much more quickly c 13 dienes locked into s trans conformation don t react at all iv reaction usually proceeds faster when alkene is electron deficient such as with a carbonyl group attached 13 diene is neutral or electron rich such as with a heteroatom attached V as a result of d 39 39 y of alkene is preserved in product vi as a result of concerted mechanism out groups in 13 diene become cis in product as do the in groups viisubstituted 13 dienes react by ortho para rule regiochemistry and out endo cis rule stereochemistry viii retron for D A reaction is cyclohexene a disconnect C3 4 and C5 6 bonds 339 bond is C1 2 b erase aquot bond at C1 2 c put new 339 bonds at C2 3 C1 6 and C4 5 d even when a cyclohexane ring does not have a aquot bond a aquot bond may be introduced v retrosynthetically


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