click below
click below
Normal Size Small Size show me how
CHEM 245- Unit 2
Question | Answer |
---|---|
all reactions of benzene are | substitution reactions (to keep aromatic ring structure) |
electron donating groups bond at | 50% ortho, 50% meta |
electron withdrawing groups bond at | 81% meta |
rules for determining aromaticity | cyclic, p-orbital, every p-orbital must overlap, pi cloud must contain an odd pair of electrons (4n+2 total electrons) |
2 most important aromaticity rules | cyclic, 4n+2 total electrons |
when do molecules become non-superimposable mirror images? | >2 substitutions |
clockwise stereochemistry | R |
counterclockwise stereochemistry | S |
chiral | not identical to its mirror images |
achiral | has an internal plane of symmetry |
clockwise (optically) | dextrorotatory (+) |
counterclockwise (optically) | levorotatory (-) |
diastereomer | non-superimposable, non-mirror images |
do diastereomers have the same physical properties? | no |
do enantiomers have the same physical properties? | yes |
# of stereoisomers | 2^(chirality centers) |
meso compounds | mirror image, rotate 180 is the same as original *have chirality centers, but achiral because of the mirror plane |
organohalide elimination trend | more stable with tertiary compounds |
rate law SN2 reactions | k[Nu][R3C-X] |
SN2 reactions | occur in a single step without an intermediate |
SN2 rates | fastest with fewest substitutions; less electronegative anions=better |
SN2 leaving groups | gases are best; stable anions of strong acids 2nd |
what does SN2 stand for? | substitution nucleophilic bimolecular |
what does SN1 stand for? | substitution nucleophilic unimolecular |
rate law SN1 reactions | k[starting material] |
SN1 only occurs under ____ conditions | neutral or acidic |
RDS SN1 | carbocation formation |
are SN1 stereoselective? | nope |
SN1 leaving groups | similar to SN2; less electronegative anions; H2O neutral, OH acidic |
rate law E2 | k[reactant][base] |
E2 requires | an antiperiplanar relationship between a H and LG |
acyclic E2 | more highly substituted alkene is formed (same as cyclic if available) |
E1 rate law | k[starting material] |
if substrates that work well with both E1 and SN1 are combined... | a mixture of SN1 and E1 products will form |
primary alkyl halides will use what mechanism(s)? | SN2 if good nucleophile present E2 if no good nucleophile (base like (CH3)3O) |
secondary alkyl halides will use what mechanism(s)? | SN2 if good nucleophile present- weakly basic E2 if no good nucleophile (base like (CH3)3O) |
tertiary alkyl halides will use what mechanism(s)? | SN1 or E1 under acidic or neutral E2 if basic |
SN2 needs an available ___ to occur | sigma * |
SN1 won't occur if _____ is happening on the molecule | ring strain |
E2 likes what base? | t-butoxide |
E1 makes a | double bond |