Chapter 8

Question 1

Dehydrohalogenation

Answer 1

net loss of HX

Question 2

Dehydration

Answer 2

net loss of H2O

Question 3

Halogenation

Answer 3

net addition of X2, anti addition, formation of two c-x bonds

Question 4

Halohydrin formation

Answer 4

net addition of HOX

Question 5

Hydration

Answer 5

net addition of H2O

Question 6

3 Hydration methods

Answer 6

1) strong acid catalyst, 2) Oxymercuration (Demurcuration), 3) Hydroboration (oxidation)

Question 7

Oxymercuration/Demurcuration

Answer 7

addition of Mercury II Acetate & tetrahydrofuran or water with sodium borohydride. Produces a mercurinium intermediate, produces a markovnikov product

Question 8

Hydroboration/Oxidation

Answer 8

addition of borane and THF with hydrogen peroxide and hydroxide. results in syn addition of OH and H, anti markovnikov result (OH adds to less substituted C).

Question 9

When Carbon is reduced is ___ electron density.

Answer 9

gains

Question 10

Carbon is reduced by 2 methods

Answer 10

1. new bond between Carbon and less EN atom or 2. breaking a bond between C and a more EN atom (ONX).

Question 11

Hydrogenation

Answer 11

net addition of H2; Pd/c or PtO2 (Adam’s catalyst), results in syn addition of H to each C. These H are sensitive to steric environment of C=C. They are selective for nonaromatic C=C over other pi bonds.

Question 12

oxidation of C ____ the electron density of the atom

Answer 12

decreases

Question 13

oxidation of C by two methods

Answer 13

formation of new bond between C and more EN atom, break bond between C and less EN atom

Question 14

Epoxidation

Answer 14

formation of triangle ring with O and C2

Question 15

Epoxidation by peroxyacid

Answer 15

results in epoxide and carboxylic acid; syn addition

Question 16

Epoxidation by elimination of HX from a Halohydrin

Answer 16

addition of hydroxide and h2o to a halohydrin, removes a anion halide, produced h2o and epoxide

Question 17

Hydroxylation

Answer 17

addition of 2 OH

Question 18

Hydroxylation by hydrolysis of an epoxide

Answer 18

addition of hydronium to epoxide results in hydroxylation anti addition of 2OH

Question 19

hydroxylation by Osmium tetroxide

Answer 19

addition of OsO4, followed by NaHSO3 and H2O or OsO4 and NMO. results in syn addition of 2OH

Question 20

Ozonolysis

Answer 20

the reaction of ozone with an alkene to produce 2 carbonyls. The two carbonyls depend on the degree of substitution of the alkene. disubstituted-two aldehydes. tri- 1 aldehyde, 1 ketone tetra - 2 ketones

Question 21

Oxidation w/ KMnO4

Answer 21

alkenes with c-h bonds become carboxylic acids.

Question 22

Oxidation of diols with HIO4

Answer 22

both OH are replaced with an O.