Organic Chemsitry II Final
Organic Chemsitry II Final Chem 342
U of L
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This 19 page Study Guide was uploaded by Mary-elizabeth Notetaker on Monday April 25, 2016. The Study Guide belongs to Chem 342 at University of Louisville taught by Dr. Richter in Spring 2016. Since its upload, it has received 90 views. For similar materials see Organic Chemistry 2 in Chemistry at University of Louisville.
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Date Created: 04/25/16
“units of unsaturation” = (# H atoms in “parent” saturated compound - # H atoms in “actual” compound )/2 # H atoms in “parent” saturated compound = 2n + 2 Ignore O Treat halogens as H Every N reduces “removes” 1 H in compound from count IR C:triple:N 2260-2200 C:triple:C 2260-2100 C=C 1680-1600 C=N 1650-1550 Benzene: 1600, 1500-1430 o Flat but rigid btwn 2000 & 3000 C=O 1780-1650 o Carbonyl ~1700…ketone characteristic Strong… small peak >~3000 o Aldehyde also has weak Fermi Doublet (2820 & 2720) Carbonyl peak slightly above 1700 o Ester absorbs a little more further up C-O 1250-1050 C-N 1230-1020 O-H o In alcohol: 3650-2500 broad o In carboxylic acid: 3300-2500 very broad & ~short Merges with sp2 peaks Wider carbonyl group peak N-H 3500-3300 o Amino: mild peak ~ 3200/3300 # fingers= # H’s attached to N If no H’s will be no N peak o Amide: carbonyl peak is broad and above 1700 Sp2 C peak attaches to Fermi Doublet peak ~3200 C-H 3300-2700 NMR- more e- withdrawing group=more deshielded(downfield) Methyl protons: ~1 Allylic protons: 1.5-2.5 Halogens: 2.5-4.5 Methylene protons: ~3.2 Vinylic: 4.5-6.5 Benzene protons: 6-8 Aldehyde or carboxylic acid: >9 To find splitting pattern: # protons bonded to atom + 1 NBS- selective reduction w/ Hbr addition DBU- Aromaticity: Cyclic, planar, sp/sp2 hybridized atoms in ring Huckle’s Rule: 4n+2 pi electrons delocalized Activators(top..ortho/para)/Deactivators(bottom…meta): Amines: NH2,NHR,NR2 OH/OR R groups Halogens(deactivate but o/p) CHO,COR,COOR,COOH, Amid o Sometimes esters if connected through carbonyl, bc deactivated CN SO3H +NO2 +NR3 In reactions producing molecules with electrophilic C’s, the most electrophilic is the most favored LG(Z) ability exs: Cl>OCH3 OCOR>NHCH3 OH>NH2 Difficult to remember.. BH3 w/ H2O2 & -OH replaces C=C with OH on one C and H on the other KmNO4 turns all open allylic positions into carboxylic acids(CA) H3PO2 takes +N2 H CrO3/H2SO4 adds O3 to ring O3/H20 takes C:triplebond:C to CA CrO3 takes OH CA Most acidic has ability to accept most H’s (?) More electrophilic group makes reaction more favorable/faster (?) Pi bonds are broken during the slow step of reactions Alpha Proton Acidity: Carbons in organometallics(and ylides) are nucleophilic Also: Carbons with negative charge Generally equilibrium in a reaction lies to the side with charged molecules, and opposite the side with excess of something(if applicable) Hemiacetals: one OR and one OH Acetals: 2OR
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