Organic Chemistry ACS Final

Basicity rules
-strong base: unstable/reactive (ED groups)
-weak base: stable (EW groups/more EN/bigger)
Chair conformation
-more stable equitorial (slanted)
-pointing up/pointing down=cis if both up
-elimination: trans and diaxial
Newman projection
-gauche: substituent groups adjacent to eachother
-grab middle and turn to put in plane
Enantiomers
-not superimposable mirror images
-same besides stereochemistry
Diastereomers
-mirror images but one stereocenter stays and another is changed
Meso
-at least two stereo centers
Alkene + HBr
-adds Markonikov
Fischer projection
-vertical plane: away
-horizontal plant: towards
-assign priorities
-turn 90 then put on side
Electrophilic addition to alkene
-forms carbocation
-E+ adds
1.Hg(OAc)2, H2o
2.NaBH4
alkene
-forms mercurnium ion
-no rearrangement
-Mark addition of OH
1. B2H2
2.H2O2, NaOH
alkene
-anti-Mark addition of OH
-syn addition of the H added
Br2 to alkene
-anti addition
-adds to both sides
-could be allylic shift; 1,2 and 1,4 mixture
1.H2o,H2SO4
2. HgSO4
alkyne
-Mark OH intermediate (enol)
-ketone isolated
Diels Alder
-diene: two double bonds
-dieneophile: one double bond at least; two EW groups
-partial charges line up
-maintain regioselectivity/stereoselectivity
-endo position most stable substituents (pointing down)
Acid catalyzed hydration of alkenes
-H20 is nucleophile
1. (SiaBH)2
2.H2O2, NaOH
alkyne
-anti Mark OH intermediate (enol)
-aldehyde isolated
Halogen addition to alkene
-forms ion (triangle)
-Nucleophile would attack more sub. side
Kinetic product
-fastest
-1,2 additon
-organometallics, strong basic nucleophiles
Thermodynamic product
-more stable alkene
-1,4 addition
-weak basic nucleophiles
HCCl3 and base
alkene
-forms CCl2
-makes triangle with alkene (like an epoxide)
Imine
-carbonyl and primary NH2
-forms a C=NH-R
Enamine
-carbonyl and secondary NH2
-lose water
-forms C=N-R2
1.LiAlH5
2.H3O+
-reduces aldehydes, ketones, esters, acids
NaBH4
CH3OH
-reduces aldehydes and ketones
PPh3
alkyl halide
NaH or n-butyl Li
-adds double bond C=C in place of carbonyl oxygen
CN addition to carbonyl
-reversible
-adds CN
-makes OH
Gringards and ester
-adds twice
Amides + LAH
-reduces carbonyl into akyl chain with N-R
Carboxylic acid derivative reacitivy
-acid chloride > anhydride > ester > amide
LDA
(CH3)2N-Li+
-produce enolates
Aldol
-two carbonyl atoms attack
-aldehyde more reactive than ketone
-enolate formed: double bond attacks other carbonyl carbon
-then alcohol forms on attacked carbon
-dehydration to alkene by OH-
Claisen condensation
-carbonyl with an ester
-attack alpha hydrogen; form enolate ester
-attacks 2nd eq. of ester; beta keto ester
-treat with acid
-two carbonyls
Alpha halogenation of ketones: acid cat.
-mono halogenation of alpha H
-enol tautomer
-resists futher tautomerization
Primary aklyl halide EAS
-watch for rearrangement
EWG EAS
-cant add NO2 first if wanting to add something else
Radicals
-allylic H’s weakest
-tertiary H next weakest
-retention and inversion of stereochemistry
Peroxides and radicals with alkene
-add to least substituted
-radical still on most substituted
Alkene (diene) free radical polymerization
-end radicals react to create polymer
-bonds fold in to make new double bonds
Chromic acid
-oxidizers
Hot KMnO4
-cleavage product
-oxidizer
Haloform reaction
-I2 or halogen
-KOH
-methyl ketone into carboxylic acid
-oxidizer
-into methyl ketone or acetaldehyde
Peridoic acid (HIO4)
-cleaves vicinal diols
-turns into carbonyl groups
OsO4, H2O2
or KMnO4
-alkene
-forms syn diol
IR spectrum
-lower frequency: longer wavelength
CNMR
-each different type of carbon gives signal
NH2 on IR
-double split around 3500-3300
Benzene on IR
-1600
Hoffman rearrangement (NH2/Br2)
-carboxylic acid
-amine transfers side
CNMR sp3 alkyl C
-10-30
CNMR sp3 C attached to O, N, or X
-50-70
CNMR sp
75-90
CNMR sp2
100-150
CNMR ester, amide, carboxyl C=O
160-180
CNMR aldehyde, ketone C=O
190-200
HNMR sp3 C
1
HNMR C attached to pi system
2
HNMR C attached to O
3-4
HNMR sp2 C
5-6
HNMR aromatic C
7-8
HNMR aldehyde C
10
HNMR carboxylic acid O
11-12

Get access to
knowledge base

MOney Back
Guarantee
No Hidden
Charges
Unlimited
Knowledge base
Become a Member