Orgchem

Front 1

isomer

Back 1

Isomers are different compounds with the same molecular formula

Front 2

Stereoisomer

Back 2

isomers that differ only in the way the atoms are oriented in space. They have the same functional group and the same IUPAC name except for prefi xes such as cis, trans, R, and S.

• Enantiomers—stereoisomers that are nonsuperimposable mirror images of each other (5.4).
• Diastereomers—stereoisomers that are not mirror images of each other (5.7).

Front 3

chiral

Back 3

not superimposable
upon its mirror image.

Front 4

enantiomers

Back 4

Enantiomers are mirror images that are not superimposable

Front 5

R and S configuration of stereogenic centers

Back 5

R=clockwise
S=Counter...

Front 6

Diastereomers

Back 6

stereoisomers that are not mirror images of each other

Front 7

Constitutional isomers

Back 7

isomers that differ in the way the atoms are connected to each other. aka structural isomer

• different IUPAC names
• the same or different functional groups
• different physical and chemical properties

Front 8

Max stereoisomers

Back 8

For n stereogenic centers, the maximum number of stereoisomers is 2n

Front 9

Structural Isomer

Back 9

Two compounds that have the same molecular formula but differ in the way the atoms are connected to each other. Structural isomers are also called constitutional isomers.

Front 10

Alkene + HBr/ROOR, hv --> ________

Back 10

Halogenates less substituted C

Front 11

Alkene + NBS/(hv or ROOR) --> _____

Back 11

The allyl radical is more stable than other radicals because two resonance structures can be
drawn for it

Front 12

Radical vs Ionic Bromination

Back 12

• Treatment of cyclohexene with Br2 (in an organic solvent like CCl4) leads to addition via
ionic intermediates (Section 10.13).
• Treatment of cyclohexene with NBS (+ hν or ROOR) leads to allylic substitution, via
radical intermediates.

Front 13

Halide + KOC(CH3)3, DBU, and DBN

(Bulky, nonnucleophilic bases)

Back 13

favor elimination over substitution

Front 14

Alkyll Halide + t-butoxide --> _____

Back 14

E2 Elimination rxn.

Front 15

Secondary R-X + CH3O-/DMSO -->

Back 15

SN2 Substitution
Inverts config.

Front 16

H2O and ROH

Back 16

Polar protic solvents
(O – H or N – H)

favored for E1 and SN1

Front 17

DMSO, Acetone, DMF, THF, HMPA

Back 17

Polar aprotic solvents
(no O – H or N – H)

favored for E2 and SN2

Front 18

Primary R-X + CH3O- -->

Back 18

SN2 prod

Front 19

Secondary R-X + CH3O-/CH3OH -->

Back 19

E2 Prod

Front 20

Tertiary R-X + CH30- -->

Back 20

E2 Prod

Front 21

Tertiary R-X + CH3OH/hv -->

Back 21

SN1 Prod

Front 22

Tertiary R-X + acetone/hv -->

Back 22

E1 Prod

Front 23

Nucleophiles for Sub

Back 23

-CN, N3-, HS-
CH3O- (Strong base)
CH3OH

Front 24

Most reactive halide?

Back 24

Primary>secondary>tertiary

more room for Nu to attack.

Front 25

Strong Nucleophiles

Back 25

neg charge, have weak conj acid, stronger going left and down the periodic table

Ex. OH-, I- in polar protic solvent

Front 26

The Zaitsev rule:

Back 26

The major product in a elimination has the more substituted double
bond.