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CHM 234| Pericyclic Reaction (Cont.)

by: Alvin Notetaker

CHM 234| Pericyclic Reaction (Cont.) CHM 234

Marketplace > Arizona State University > Chemistry > CHM 234 > CHM 234 Pericyclic Reaction Cont
Alvin Notetaker
GPA 3.33

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About this Document

Topic Pericyclic Reaction Aromatic chapter
General Organic Chemistry II
Class Notes
Organic Chemistry
25 ?




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This 7 page Class Notes was uploaded by Alvin Notetaker on Sunday March 20, 2016. The Class Notes belongs to CHM 234 at Arizona State University taught by Pillai in Fall 2015. Since its upload, it has received 17 views. For similar materials see General Organic Chemistry II in Chemistry at Arizona State University.

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Date Created: 03/20/16
Pericyclic Reactions    Predicting the product when both reagents are unsymmetrically substituted  D ­ Donating group  W ­ Withdrawing group  Formation of 1,4 ­ Product    Example:    Formation of 1,2 ­ Product    Example:      The formation of ​ 1,3 ­ Product​ will not form.    If a Diels–​Alder reaction creates a product with a chiral center, than it will product a racemic  mixture.    Retrosynthetic Analysis of the Diels Alder Reaction      MO Description of Cycloadditions  If there is a conversation of orbital symmetry, then it is symmetry­allowed​ .  When the orbital doesn’t overlap, it is ​symmetry­forbidden.​     This is a [2+2] cycloaddition. Here, an electron in the HOMO will move to LUMO in the other.  When [2+2] cycloaddition is react with ​ heat, the orbital will create symmetry­forbidden, so​  light  is the only way a [2+2] cycloaddition can react.      Electrocyclic Reactions      Thermal  Photochemical (light)  Four π electrons  Conrotatory  Disrotatory  Six π electrons  Disrotatory  Conrotatory  Disrotatory​ ­ New sigma orbital will rotate ​opposite​  of each other to form a sigma bond.  Conrotatory​  ­ New sigma orbital will rotate the ​same ​way of each other to form a sigma bond.    Six π electrons  Thermal & Photochemical    Four π electrons  Thermal & Photochemical      Sigmatropic Rearrangements  [3,3] Sigmatropic rearrangement  Shows where the new sigma bond forms (3 position) and where the old sigma bond breaks (1  position).    The Cope Rearrangement  A [3,3] sigmatropic rearrangement where ​ all six of the cyclic system is carbon​ .      The Claisen Rearrangement  A [3,3] sigmatropic rearrangement where it is observed to have ​ vinylic ethers​ .    Example:      [1,5] sigmatropic rearrangement    Example:      UV­Vis Spectroscopy  The ​necessary energy​ , excited electron from HOMO to LUMO, is either the ​ UV or visible  region ​ of the spectrum.  UV­Vis spectroscopy gives ​ structural information​  about molecules.    A = log   I0 I   More conjugation gives a smaller HOMO to LUMO gap.    Chromophore ​ ­ Absorbing UV­VIS light (The conjugated chain).  Auxochromes ​ ­ Group of atoms attached to a chromophore.      Chapter 18 Aromatic Compounds  Aromatic includes benzenes and benzene derivatives.    Nomenclature of Benzene Derivatives  Monosubstituted Derivatives of Benzene  For some compound, the name comes from the parent name (benzene).    Other names:    If the substituent chain has a longer carbon chain, then it will become the parent chain.    1­phenylheptane    Disubstituted Derivatives of Benzenes  Based on the position of two substituents, it will be either ortho, meta, para.  Ortho = adjacent  Meta = separated by one carbon  Para = Opposite of one another      1,2­dibromobenzene  ortho­dibromobenzene    Common name for dimethyl benzene is x ​ylene    meta­xylene  1,3­dimethylbenzene    Polysubstituted Derivatives of Benzenes  ● Identify and name the parent  ● Identify and name the substituents  ● Assign a locant to each substituents  ● Arrange the substituents alphabetically      Parent chain  Name  Phenol  4­bromo­2­methylphenol  Toluene  5­bromo­2­hydroxytoluene  Benzene  4­bromo­1­hydroxy­2­methylbenzene      Stability of Benzene    Benzene is stable because its bonding orbitals are filled with electrons.    Cyclobutadiene and Cyclooctatetraene stability  Both are unstable. There MO are not filled with electrons like benzene.  Cyclobutadiene react with itself at ­78°C to make cyclooctatetraene.    Hückel’s Rule  A cyclic compound must have odd number of pi electrons pairs to be aromatic.    Aromatic Compounds  ● Cyclic  ● Planer  ● Every ring atom must have a p orbital  ● Odd number of pair of pi electrons    MO Theory and Frost Circles    The unpaired electron makes cyclobutadiene very reactive.  The unpaired electrons makes this a ​ntiaromatic. 


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