Orgo Exam 2 General

2 main factors of all reactions

steric hindrance, electronics (hyperconjugation and resonance)

in nucleophile we have electron density in the ____, aka the _____ reactive orbital

HOMO, highest

in electrophiles, we have electron density in the ____, aka the _____ energy orbital

LUMO, lowest

Sn2 attacks from ______ the carbon. If Nu wants to break C-LG, it must ______ donate electrons to largest region of space _______ C. Stereochemistry inverts Y/N

behind, donate, behind, Y

sp3 carbons prefer ____ bond angles, so epoxides are ______

109.5, strained

synthesis of epoxides needs _ or _ _____ ______, _ won’t work.

1’, 2’, alkyl halide, 3’

synthesis of epoxides electronically requires _____ ___________ between _-_ and _-_ for proper orbital overlap

anti conformation, C, O, C, LG

conjugation definition

3+ adjacent atoms with aligned p orbitals

isolated

pi bonds separated by sp3 C

cumulated

adjacent double bonds, sp C, 90 degrees don’t interact

conjugated

all p orbitals parallel, electrons delocalized over 4 C atoms

only ________ lone pairs can be parallel per atom. If atom is already drawn participating in pi bond, lone pairs _____ be parallel. If atom is drawn ________ to __ ____, then lone pair can be parallel and conjugated.

perpendicular, can’t, adjacent, pi bond

molecules that ____ conjugation by reacting tend to be less reactive

lose

molecules that ____ conjugation by reacting tend to be more reactive

gain

aromaticity factors

cyclic, conjugated, planar, 4n+2 pi e

what doesn’t affect aromaticity

division in a ring, heteroatoms, ring size, charge

what does affect aromaticity

resonance

functional groups that ______ e density make ring ____ nucleophilic than benzene and activating it bc of _____________ and ___________ _____ ______

donate, more, hyperconjugation, conjugated lone pairs

NH2 leaving group is

super nucleophilic

functional groups that ______ e density make ring ____ nucleophilic than benzene and ________ it bc of _____________ and ___________ to polarized pi bond outside of ring

remove, less, deactivate, induction, conjugation

EWG Rankings

Ar-NO2, Ar-SO2Me, Ar-C—-N, Ar-ketone

the ____ deactivated for EAS, the ______ for SnAr

more, better

leaving groups ranking

F, Cl, Br, I

best leaving group of all for SnAr

diazonium (N2)