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CHEM:341 Organic Chemistry I Week 7 Notes

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CHEM:341 Organic Chemistry I Week 7 Notes CHEM341

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About this Document

These cover week 7 notes on rings, acidity/bacisity, and nomenclature.
Organic Chemistry
Anna Elizabeth Allen
Class Notes
Organic Chemistry, nomenclature, Rings, Cyclohexane, substituted cyclohexanes
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This 10 page Class Notes was uploaded by Raffasarru on Friday October 7, 2016. The Class Notes belongs to CHEM341 at Colorado State University taught by Anna Elizabeth Allen in Fall 2016. Since its upload, it has received 5 views.


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Date Created: 10/07/16
CHEM:341 Modern Organic Chemistry I Week 7 Notes  Monosubstituted cyclohexane Rings o Methylcyclohexane  Can be substituted in axial or equatorial positions (conformers)    For every one axial conformation, we have 20 equatorial conformations (1:20 ratio)  Trend in monosubstituted cyclohexane rings: Group ???? ????????(equatorial to axial) Methyl 20:1 Ethyl 21:1 Propyl 43:1 Isopropyl 86:1 Tert-butyl 12,000:1 1   Tert-butyl is always equatorial because of the diaxial interactions above o A-Values  A-values are the energy difference between equatorial and axial monosubstituted cyclohexanes  Can be used to estimate size of cyclohexane substituents  Disubstituted Cycloalkane Rings o Isomers possible: cis or trans, and R or S (NO E or Z, only for alkenes) o Stereoisomers: isomers that differ only in the way atoms are oriented in space  Disubstituted Cyclohexane Rings o Consider: 1,4-dimethylcyclohexane  Two possible isomers:   Top is cis, bottoms is trans  Cis has same energy, same stability for each conformation  Trans: the conformation with two equatorial methyl groups is lower energy and more stable o Consider: 1,3-dimethylcyclohexane  Two possible isomers: 2   Top is cis, bottoms is trans  Trans has same energy, same stability for each conformation  Cis: conformation with two equatorial methyl groups is lower energy and more stable  1,3-diaxial interactions: interaction between two axial substituents on the same side of the ring (avoid if possible, high energy)  o Examples: 3  Chapter 6: Acidity and Basicity  Acidity and Basicity o Bronsted-Lowry Acid Definitions: +  Acid is a proton donor (or loses ???? ions) +  Base is proton acceptor (or gains ???? ions (has available set of electrons)) o Bronsted-Lowry Acid/Base reactions are proton transfer reactions o Proton transfers from acid to base − + o ???? − ???? + ???? ⇌ ???? + ???????? o Acid strength is tendency of an acid to donate a proton  Measure strength with ????????  Larger ???? ???? stronger acid (more likely to donate a proton)  However, organic acids are generally week and have very small???????? values −5 −50 (10 to 10  More convenient to use ????????????instead (????????????= −log ????( ????) −5  ???? ???? 10 , ???????? = ???? −50  ???? ???? 10 , ????????????= 50  Smaller ???????? ???? stronger acid o Common ???????? Val????es 4 Acid ???????????? Conjugate Base ???????????? 2???? ????3 + −1.7 or > 0 ????????????,???? ????2 4.8 or 5 + ???? 3???? −9 or 10 ????3???? 10 ????????????,???? ????2 16 or 15 ???????? ,???????? − Alkyne bonded to ???? 25 Alkyne with negative charge at end ???????? 3 38 or 35 − 40 ???????? 2 ???????? 3 −50 or 50 ???? 3  Acid Strength and Conjugate Base o Strength of acid inversely relates to strength of conjugate base o ???????? +???????????? = ????4 o Strong acid donates proton, forming weak base  Conjugate base doesn’t want ???? back  ???????????? + ???? → ???? − ???? + ???????? − o Strong base accepts a proton, forming a weak acid  Conjugate acid doesn’t want to give up ????  ???????? 3 ???? − ???? → ???????? + 4 − o Inverse relationship is useful: we can u????e ???????? values to compare relative acidity of acids as well as the relative basicity of other compounds o Smaller ???????? ????eans stronger acid and weaker the conjugate base  Predicting Outcome of Acid-Base Reaction o Acid-Base reactions represent an equilibrium with two acid base pairs  Acid with its conjugate base and base with conjugate acid  ???????? + ???? ⇌ ???? + ???????? + 5  ???????? ???????????? ???? are acid, conj. base pair  ???? ???????????? ???????? are base, conj. acid pair  Position of equilibrium depends on relative strengths of acid/base pairs o Equilibrium always favors formation of weaker acid and base   Larger arrow toward weaker acid/base o Determine relative strengths of acids without specific ???????? values −  General Rule: anything that stabilizes a conjugate base ???? increases the acidity of the acid ????????  Strategy:  Find conjugate base of acid  Compare conjugate bases (stability)  Use inverse relationship  Acid Strength o Element Identity  Most important factor to determine strength of acid ???????? is the location of ???? on the periodic table  Left to right across periodic table:  Conjugate bases become more stable  Acids become more acidic  More electronegative atoms are better at stabilizing lone pairs  Top to bottom down the periodic table:  Conjugate bases become more stable, weaker  Radius increases, easier to lose ???? 6  Charge spread out over larger area  General Trend:  Across: o Acidity increases left to right o As atom bonded to proton gets more electronegative, acid gets stronger  Down: o Acidity increases top to bottom o As atom bonded to proton increases in radius (and therefore size), acid gets stronger o Inductive Effects  Electronegative atoms don’t have to be directly bonded to the acidic proton to affect acidity. Nearby electronegative atoms will increase the acidity by acting as an electron-withdrawing group  Inductive Effect: pulling of electron density through sigma bonds due to differences in electronegativity   General Rules  Greater electronegativity, greater stabilization (weaker acid)  Closer electronegative, greater stabilization (weaker acid)  Greater number of electronegative atoms, greater stabilization (weaker acid) 7 o Resonance  Ability to draw resonance structures for conjugate base will have big impact on acidity  Ethanol vs. acetic acid  vs.  Ethanol: charge localized on oxygen, stronger base  Acetic Acid: charge delocalized (shared over two atoms) so it’s more stable, stronger acid  General Rule: those with resonance structures make more stable conjugate bases and are stronger acids o Hybridization  Hybridization of the atom directly bonded to proton being lost has big impact on acidity % ???? character Bond (not always, Acidity but general) 25% Single Weakest 33% Double Middle 50% Triple Strongest  General Rule: Higher % ???? character an orbital has, the more stable the electrons that occupy it: more stable conjugate base, stronger acid o Charge  Overall charge of conjugate base has impact on acidity  General Rule: Neutral conjugate base is more stable than a charged conjugate base, stronger acid  Comparing Acids Examples: 8 o o A carboxylic acid would be a sronger acid than the middle one because the middle one only has one major resonance structure while acetic acid has two  Base Strength: any factors that increase the acidity of an acid also decrease the bacisity of conjugate base o Element Identity:  Same row of periodic table, most basic on left (less electronegative)  Same column (group) of periodic table, most basic (smaller radius/size) o Inductive Effects: Weaker inductive effects (nearby electronegative groups) decrease bacisity o Resonance:  Fewer resonance structures increases bacisity  Must be able to use pair of electrons that would attack proton o Hybridization: Smaller % ????-character increases bacisity o Charge: Negatively charged molecules will be more basic than neutral ones  Organic Nomenclature: Alcohols, Amines, and Ethers o Alcohols and amines take priority when it comes to nomenclature and change suffix of name  Find longest carbon chain that contains priority group  Change -e ending to appropriate suffix:  Alcohols: -ol  Amines: -amine  If more than one, di-, tri-, tetra-, etc. are added before suffix  Number carbons to give priority group lowest number o Ethers have no priority and are treated as an alkoxy substituent with -oxy following the carbon chain length on shorter side o Examples: 9   2-ethoxybutane    2-ethyl-3-methylbutan-1-ol   2,2-dimethyl-1,3-propanediol    N,N-diethyl-2-methylpropanamine 10


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