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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 |