Organic Chemistry ACS Final Exam Study Questions and Answers with Complete Solution 2024

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