Organic Chemistry ACS Final
Basicity rules - ANS -strong base: unstable/reactive (ED groups)
-weak base: stable (EW groups/more EN/bigger)
Chair conformation - ANS -more stable equatorial (slanted)
-pointing up/pointing down=cis if both up
K
-elimination: trans and diaxial
C
Newman projection - ANS -gauche: substituent groups adjacent to each other
-grab middle and turn to put in plane
LO
Enantiomers - ANS -not superimposable mirror images
-same besides stereochemistry
Diastereomers - ANS -mirror images but one stereocenter stays and another is
changed
YC
Meso - ANS -at least two stereo centers
Alkene + HBr - ANS -adds Markonikov
D
Fischer projection - ANS -vertical plane: away
-horizontal plant: towards
U
-assign priorities
-turn 90 then put on side
ST
Electrophilic addition to alkene - ANS -forms carbocation
-E+ adds
1.Hg(OAc)2, H2o
2.NaBH4
alkene - ANS -forms mercurnium ion
-no rearrangement
-Mark addition of OH
1. B2H2
, 2.H2O2, NaOH
alkene - ANS -anti-Mark addition of OH
-syn addition of the H added
Br2 to alkene - ANS -anti addition
-adds to both sides
-could be allylic shift; 1,2 and 1,4 mixture
1.H2o,H2SO4
2. HgSO4
K
alkyne - ANS -Mark OH intermediate (enol)
-ketone isolated
C
Diels Alder - ANS -diene: two double bonds
-dieneophile: one double bond at least; two EW groups
LO
-partial charges line up
-maintain regioselectivity/stereoselectivity
-endo position most stable substituents (pointing down)
Acid catalyzed hydration of alkenes - ANS -H20 is nucleophile
YC
1. (SiaBH)2
2.H2O2, NaOH
alkyne - ANS -anti Mark OH intermediate (enol)
-aldehyde isolated
D
Halogen addition to alkene - ANS -forms ion (triangle)
U
-Nucleophile would attack more sub. side
Kinetic product - ANS -fastest
ST
-1,2 additon
-organometallics, strong basic nucleophiles
Thermodynamic product - ANS -more stable alkene
-1,4 addition
-weak basic nucleophiles
HCCl3 and base
alkene - ANS -forms CCl2
-makes triangle with alkene (like an epoxide)
Basicity rules - ANS -strong base: unstable/reactive (ED groups)
-weak base: stable (EW groups/more EN/bigger)
Chair conformation - ANS -more stable equatorial (slanted)
-pointing up/pointing down=cis if both up
K
-elimination: trans and diaxial
C
Newman projection - ANS -gauche: substituent groups adjacent to each other
-grab middle and turn to put in plane
LO
Enantiomers - ANS -not superimposable mirror images
-same besides stereochemistry
Diastereomers - ANS -mirror images but one stereocenter stays and another is
changed
YC
Meso - ANS -at least two stereo centers
Alkene + HBr - ANS -adds Markonikov
D
Fischer projection - ANS -vertical plane: away
-horizontal plant: towards
U
-assign priorities
-turn 90 then put on side
ST
Electrophilic addition to alkene - ANS -forms carbocation
-E+ adds
1.Hg(OAc)2, H2o
2.NaBH4
alkene - ANS -forms mercurnium ion
-no rearrangement
-Mark addition of OH
1. B2H2
, 2.H2O2, NaOH
alkene - ANS -anti-Mark addition of OH
-syn addition of the H added
Br2 to alkene - ANS -anti addition
-adds to both sides
-could be allylic shift; 1,2 and 1,4 mixture
1.H2o,H2SO4
2. HgSO4
K
alkyne - ANS -Mark OH intermediate (enol)
-ketone isolated
C
Diels Alder - ANS -diene: two double bonds
-dieneophile: one double bond at least; two EW groups
LO
-partial charges line up
-maintain regioselectivity/stereoselectivity
-endo position most stable substituents (pointing down)
Acid catalyzed hydration of alkenes - ANS -H20 is nucleophile
YC
1. (SiaBH)2
2.H2O2, NaOH
alkyne - ANS -anti Mark OH intermediate (enol)
-aldehyde isolated
D
Halogen addition to alkene - ANS -forms ion (triangle)
U
-Nucleophile would attack more sub. side
Kinetic product - ANS -fastest
ST
-1,2 additon
-organometallics, strong basic nucleophiles
Thermodynamic product - ANS -more stable alkene
-1,4 addition
-weak basic nucleophiles
HCCl3 and base
alkene - ANS -forms CCl2
-makes triangle with alkene (like an epoxide)
