chm 2210 organic chemistry 1 final review, jeslin

7/23/2019 CHM 2210 Organic Chemistry 1 Final Review, Jeslin

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Organic Chemistry 1 Final Review Instructor: Dr. Frazer

SI Leader: eslin

Constitutional Isomers: Diferent compounds that have the samemolecular ormula but diferent in the sequence in which their atomsare bonded, that is, their connectivity but not number o bonds (olderterm: structural isomers.

Chemical Bonds: he !ctet "ule# $ow to %rite &ewis 'tructures#

)ceptions to the !ctet "ule

* lectrone+ativity: he ability o an atom to attract electrons

* lements o the third period and beyond have d orbitals that can beused or bondin+ and thus can e)ceed the octet rule (e+: ' or -

* lements such as boron and beryllium can have ewer than ei+htelectrons (e+: B/-

* !)y+ens are very rarely bonded to other o)y+ens in stable moleculesbecause these pero)y +roups are very unstable and reactive.


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ormal Char+es

* 0 1 -(B 2 3-, where 1 is the +roup number, B is one electron or

each covalent bond and 3 is the number o unshared electrons.

"esonance heory

*"esonance structures are not real representations o the actualmolecule.

* he actual molecule is a hybrid o all resonance contributors

* 4 double5headed arrow is used to equate resonance structures

* "esonance structures stabili6e a molecule or ion, especiallywhen the resonance structures are equivalent and is7nown as resonance stabili6ation

* he more stable an individual resonance contributor is on its own,the +reater its contribution to the overall hybrid structure


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Determination o 'tability or "esonance 'tructures

*he ollowin+ is in order o decreasin+ si+ni8cance:

9. he more covalent bonds a structure has, the more stable it is

. Char+e separation (ormal char+es- decreases stability

/. ;e+ative char+es on the more electrone+ative elements andpositive char+e on the more electropositive elements are more

avorable


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* he auli )clusion rinciples states that a ma)imum o twoelectrons may be placed in each orbital but only when the spins othe electrons are paired.* $und>s "ule states that, when de+enerate orbitals are considered,we add one electron to each with their spins unpaired until each

de+enerate orbital contains one electron. 4terward, the second seto electrons are aided to pair the spins.

sp, sp, sp/$ybridi6ation, shape and an+le


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unctional ?roups

"eactions and heir =echanisms

* 'ubstitutions are the characteristics reactions o saturatedcompounds such as al7anes and al7yl halides and oaromatic compounds where one +roup replaces another

* 4dditions are characteristic o compounds with multiple bondswhere all parts o the addin+ rea+ent appear in the product

* liminations are the opposite o additions where one moleculesloses the elements o another small molecule

* liminations are useul in creatin+ compounds with multiplebonds


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* "earran+ements are when a molecule under+oes areor+ani6ation o its constituent parts

4cid5Base "eactions

* 4 Br@nsted5&owry acid is a substance that can donate a proton* 4 Br@nsted5&owry base is a substance that can accept a proton* 4ccordin+ to &ewis acid5base theory, acids are electron pairacceptors while bases are electron pair donors

* 4 carbocation is an ion with a positive char+e on the carbon atomwhile a carbanion is an ion with a ne+atively char+e carbon atom.* Carbocations, and all lewis acids, are electrophiles, which means

that they are electron5see7in+ rea+ents to achieve a ull octet.* Carbanions, and all lewis bases, are nucleophiles, which meansthey see7 a positive center other than a proton, especially that o apositively char+ed carbon atom!RIO""""""Standard Free#$nergy Change% delta &

I34C ;omenclature* ndin+s o al7ane names end in 5ane, and the standard pre8)esapply to how many carbon atoms there are (meth5, eth5, prop5, but5,

pent-

, etc.-* 4n al7yl +roup has one hydro+en removed rom an al7ane, and thenames have a suA) o yl.* 4n alcohol +roup has the name endin+ o ol.

;omenclature or Bicyclic Compounds* Bicycloal7anes are compounds containin+ two used or brid+edrin+s with the name o the al7ane correspondin+ to the total numbero carbon atoms


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* he carbon atoms common to both rin+s are 7nown asbrid+eheads with each bond or chain o atoms connectin+ thebrid+ehead atoms bein+ called a brid+e* %ith the name, we also interpose an e)pression in brac7ets thatdenotes the number o carbon atoms in each brid+e in order o

decreasin+ len+th. used rin+s have 6ero carbon atoms in the brid+e(e+:Bicyclo..9heptane-* ;umber the lar+est cyclic section 8rst rom the brid+ehead

;ewman roEections

Chair Conormations (rin+ Fips-

Chirality, 'tereochemistry, and Isomerism

* Chiral obEects are those that can e)ist in ri+ht and let handedorms

* I the mirror ima+e o an obEect can be superposed onto itsel thenit is considered achiral

* Isomers are diferent compounds that have the same molecularormula

* Constitutional isomers have the same molecular ormula butdiferent connectivity

* 'tereoisomers have their atoms connected in the same sequence,but they difer in the arran+ement o their atoms in space (e+: cisand trans isomers-

* nantiomers are stereoisomers whose molecules are non5superimposable mirror ima+es o each other (optical isomers-

* Diastereomers are stereoisomers whose molecules are not mirrorima+es o each other

* o create a diastereomer +iven the structure o one molecule

simply chan+e a dashed wed+e to a solid wed+e99, or vice versawithout it creatin+ a mirror ima+e or do a cis5trans swap

* 4 chiral molecule is one that is not superimposable on its mirrorima+e (thereore, all enantiomers are pairs o chiral molecules-

* 4 molecule will not be chiral i it possess a plane o symmetry(meso compound-


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* " and ' systemGG

'ubstitution and limination reactions


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4ddition "eactions


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4lcohols and thers


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po)ides

4cid Cataly6ed

'now the (ase#catalyzed ones too"


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4lcohols

?"I?;4"DG

chm 2210 organic chemistry 1 final review, jeslin

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