Organic midterm 2

cis-2-butene

trans-2-butene

(Z)-1-bromo-2-chloropropene

(E)-1-bromo-2-chloropropene

Priority rules

1a: Higher atomic number = higher priority

1b: Higher isotopic mass = higher priority

2: If level 1 atoms are the same, work outward until first point of difference

HBr, HI, HCl addition

Halogen goes to most substituted C, alkynes do the same, but twice

Halide addition mechanism (alkene)

Alkyl/Hydride shift

Occurs when intermediate is much more stable (higher degree carbocation), only shifts once

Transition state

an unstable state of maximum free energy (energy barrier) that reactants must pass through as they change to products

Hydrogenation of alkenes

Acid Catalyzed Hydration

Bromohydrin formation mechanism

Br2, H2O

Addition of Br2 mechanism

Oxymercuration-reduction mechanism

Hydroboration-oxidation mechanism

Ozonolysis mechanism

1% HBr, H2O

Anti-Markovnikov HBr addition mechanism

HBr, ROOR

chiral

a chiral object is one that is not superimposable on its mirror image ex. left and right hands

isomer

same chemical formula

constitutional isomer

same formula but different connection

stereoisomer

same formula and connection, different spatial arrangement

enantiomer

mirror image (all centers inverted)

diastereomer

all stereoisomers that are not enantiomers (some but not all centers are inverted)

asymmetric carbon

meso compound

achiral compound with asymmetric carbons

racemate (racemic mixture)

1:1 mixture of two enantiomers, optical rotation: 0

stereocenter

an atom at which the interchange of 2 groups gives a stereoisomer (sp2 and sp3 C)