front 1 Polar Aprotic Solvents | back 1 F- > Cl- > Br- > I- Nucleophilicity = Basicity Solvates cations |
front 2 Polar Protic Solvents | back 2 I- > Br- > Cl- > F- Nucleophilicity /=/ Basicity Solvates cations and anions |
front 3 SN1 Reactions | back 3 - formation of a carbocation - love polar protic solvents - result in EQUAL mixture of stereoismers (R and S) racemic mixture - 3 > 2 > 1 > CH3 (1 and CH3 do not do SN1 reactions) |
front 4 SN1 Reaction Rate | back 4 only the concentration of the alkyl halide affects the reaction rate rate = [alkyl halide] |
front 5 SN2 Reactions | back 5 - backattack - love polar aprotic solvents - can result in inversion of configuration if reaction is on a chiral carbon (if not, config. is retained) - CH3 > 1 > 2 > 3 (3 does not undergo SN2) |
front 6 E1 and E2 Reaction | back 6 3 > 2 > 1 |
front 7 SN2 Reaction Rate | back 7 concentration of alkyl halide and nucleophile affects reaction rate [alkyl halide][Nu] |
front 8 Examples of polar protic solvents | back 8 H20, MeoH, EtOH, acetic acid, ammonia (contains a Hydrogen) |
front 9 Examples of polar aprotic solvents | back 9 DMSO, DMF, acetone, acetonitrile, CN-, I- |
front 10 Elimination is favored when | back 10 - using a strong base (pka > 14) and has a negative charge - high temperature - 2 or 3 alkyl halide - using a strong, bulky base such as isopropyide or tert-butoxide |
front 11 Zaitsev's Rule | back 11 formation of the most substituted alkene is favored with a small base this is because the most substituted alkene is the most stable most stable -> major product |
front 12 E2 reactions on cyclic molecules | back 12 must be anti-coplanar |
front 13 Cis formations on cyclic molecules yield how many products | back 13 2 |
front 14 Trans formations on cyclic molecules yield how many products | back 14 1 |
front 15 True/False Trans alkenes are more stable than cis alkenes | back 15 True |
front 16 when 2 alkenes can be formed, the most substituted will predominate when... | back 16 a strong unhindered base is used |
front 17 when 2 alkenes can be formed, the least substituted will predominate when... | back 17 a strong, bulky base is used |
front 18 when substituents are all facing up, the molecule is... | back 18 cis |
front 19 when one substituent is facing up and the other is facing down, the molecule is... | back 19 trans |
front 20 the halogen must be _____ in order to react with a labile hydrogen. | back 20 anti-coplanar |
front 21 What kind of reagent would you use to eliminate a halogen? | back 21 A strong, bulky base |
front 22 Basicity is a ____ matter | back 22 thermodynamic |
front 23 Nucleophilicity is a _____ matter | back 23 kinetics |
front 24 Regioselectivity | back 24 When more than one constitutional isomer is produced and one predominates |
front 25 Stereoselectivity | back 25 When more than one stereoisomer is produced and one predominates |
front 26 E ( entegegen) | back 26 when heaviest groups are on opposite sides of the plane (based on atomic weight) |
front 27 Z (Zusamenn) | back 27 when heaviest groups are on the same side of the plane (atomic weight) |
front 28 the most substituted has the ... | back 28 lowest heat of hydrogenation |