Organic Chemistry ACS Final (with Complete Solutions) 2024.
Basicity rules correct answers -strong base: unstable/reactive (ED groups)
-weak base: stable (EW groups/more EN/bigger)
Chair conformation correct answers -more stable equitorial (slanted)
-pointing up/pointing down=cis if both up
-elimination: trans and diaxial
Newman projection correct answers -gauche: substituent groups adjacent to eachother
-grab middle and turn to put in plane
Enantiomers correct answers -not superimposable mirror images
-same besides stereochemistry
Diastereomers correct answers -mirror images but one stereocenter stays and another is changed
Meso correct answers -at least two stereo centers
Alkene + HBr correct answers -adds Markonikov
Fischer projection correct answers -vertical plane: away
-horizontal plant: towards
-assign priorities -turn 90 then put on side
Electrophilic addition to alkene correct answers -forms carbocation
-E+ adds
1.Hg(OAc)2, H2o
2.NaBH4
alkene correct answers -forms mercurnium ion -no rearrangement
-Mark addition of OH
1. B2H2
2.H2O2, NaOH
alkene correct answers -anti-Mark addition of OH
-syn addition of the H added
Br2 to alkene correct answers -anti addition
-adds to both sides
-could be allylic shift; 1,2 and 1,4 mixture 1.H2o,H2SO4
2. HgSO4
alkyne correct answers -Mark OH intermediate (enol)
-ketone isolated
Diels Alder correct answers -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 correct answers -H20 is nucleophile
1. (SiaBH)2
2.H2O2, NaOH
alkyne correct answers -anti Mark OH intermediate (enol)
-aldehyde isolated
Halogen addition to alkene correct answers -forms ion (triangle)
-Nucleophile would attack more sub. side
Kinetic product correct answers -fastest
-1,2 additon
-organometallics, strong basic nucleophiles
Thermodynamic product correct answers -more stable alkene
-1,4 addition
-weak basic nucleophiles
HCCl3 and base
alkene correct answers -forms CCl2
-makes triangle with alkene (like an epoxide)
Imine correct answers -carbonyl and primary NH2
-forms a C=NH-R
Enamine correct answers -carbonyl and secondary NH2
-lose water
-forms C=N-R2
1.LiAlH5
2.H3O+ correct answers -reduces aldehydes, ketones, esters, acids
NaBH4
CH3OH correct answers -reduces aldehydes and ketones
Basicity rules correct answers -strong base: unstable/reactive (ED groups)
-weak base: stable (EW groups/more EN/bigger)
Chair conformation correct answers -more stable equitorial (slanted)
-pointing up/pointing down=cis if both up
-elimination: trans and diaxial
Newman projection correct answers -gauche: substituent groups adjacent to eachother
-grab middle and turn to put in plane
Enantiomers correct answers -not superimposable mirror images
-same besides stereochemistry
Diastereomers correct answers -mirror images but one stereocenter stays and another is changed
Meso correct answers -at least two stereo centers
Alkene + HBr correct answers -adds Markonikov
Fischer projection correct answers -vertical plane: away
-horizontal plant: towards
-assign priorities -turn 90 then put on side
Electrophilic addition to alkene correct answers -forms carbocation
-E+ adds
1.Hg(OAc)2, H2o
2.NaBH4
alkene correct answers -forms mercurnium ion -no rearrangement
-Mark addition of OH
1. B2H2
2.H2O2, NaOH
alkene correct answers -anti-Mark addition of OH
-syn addition of the H added
Br2 to alkene correct answers -anti addition
-adds to both sides
-could be allylic shift; 1,2 and 1,4 mixture 1.H2o,H2SO4
2. HgSO4
alkyne correct answers -Mark OH intermediate (enol)
-ketone isolated
Diels Alder correct answers -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 correct answers -H20 is nucleophile
1. (SiaBH)2
2.H2O2, NaOH
alkyne correct answers -anti Mark OH intermediate (enol)
-aldehyde isolated
Halogen addition to alkene correct answers -forms ion (triangle)
-Nucleophile would attack more sub. side
Kinetic product correct answers -fastest
-1,2 additon
-organometallics, strong basic nucleophiles
Thermodynamic product correct answers -more stable alkene
-1,4 addition
-weak basic nucleophiles
HCCl3 and base
alkene correct answers -forms CCl2
-makes triangle with alkene (like an epoxide)
Imine correct answers -carbonyl and primary NH2
-forms a C=NH-R
Enamine correct answers -carbonyl and secondary NH2
-lose water
-forms C=N-R2
1.LiAlH5
2.H3O+ correct answers -reduces aldehydes, ketones, esters, acids
NaBH4
CH3OH correct answers -reduces aldehydes and ketones
