Chp8-10 Reactions & Mechanisms

Question 1

H2 & Lindlar

Answer 1

alkyne into CIS alkene
(NOT alkane)

Question 2

H2O

Answer 2

markovnikov addition

Question 3

HBr & ROOR

Answer 3

antimarkovnikov
(ROOR is peroxide w/ free radicals)
(+enantiomer)

Question 4

Na & NH3

Answer 4

alkyne into TRANS alkene

Question 5

mCPBA

Answer 5

(is a peroxide)
makes triangle O epoxide

Question 6

2 equiv. HCl

Answer 6

H goes to less sub
then 2 Cl go to more sub
(added: 2 Cl and 2 H)

Question 7

HBr

Answer 7

Br to more sub
H to less sub

Question 8

Br2

Answer 8

add to both sides, because no H
(+enantiomer)

Question 9

Cl2 & H2O

Answer 9

Cl on less sub
OH on more sub

Question 10

O3 & Zn, H2O

Answer 10

aldehyde
(C=O)

Question 11

H2O, H2SO4 & HgSO4

Answer 11

enol -> ketone
OH -> O double

Question 12

2 equiv. Br2

Answer 12

alkane
2 Br & 2 Br

Question 13

BH3, THF & H2O2, NaOH

Answer 13

anti-markovnikov OH addition

Question 14

Hydrogenation
H2

Answer 14

syn addition

Question 15

Hydrohalogenation
HX

Answer 15

markovnikov
X on more sub
H on less sub

Question 16

Hydrohalogenation
HBr & ROOR

Answer 16

antimarkovnikov
H on more sub
Br on less sub

Question 17

Halogenation
X2 & CCl4

Answer 17

anti addition
(two Xs, on different Cs)

Question 18

Halohydrin Formation
X2 & H2O

Answer 18

anti addition
OH more sub
X less sub

Question 19

Acid Catalyzed Hydration
H2SO4 & H2O

Answer 19

anti & syn addition
marknovnikov
OH on more sub
H on less sub
H-shifting

Question 20

Hydroboration Oxidation
BH3 THF & NaOH H2O

Answer 20

anti-markovnikov
OH on less sub
H on more sub

Question 21

Epoxidation
mCPBA

Answer 21

syn addition
forms Oxygen triangle

Question 22

Dihydroxylation

Answer 22

syn addition of two OH,
not together
(or anti addition)

Question 23

Oxidative Cleavage

Answer 23

alkyne/alkene becomes alkene with C=O
(Carbons are oxidized)

Question 24

Ozonolysis
O3
(type of oxidative cleavage)

Answer 24

Add C=O to more sub
Add OH to less sub
Alkyne -> Alkene