Alkene Reactions

Question 1

H2, metal (Pd/Ni/Pt)

Answer 1

Pi bond gone/

syn addition

Question 2

H-X

Answer 2

X attaches to more sub

Question 3

H-X

mechanism

Answer 3

X leaves H-X/
Pi bond attacks H/
Carbocation created/
X attacks carbocation

Question 4

acid catalyzed hydration; reagents

Answer 4

H2O, H+ (H2SO4)

Question 5

H2O, H+ (H2SO4)

Answer 5

OH attacks more sub/

H attacks less sub

Question 6

H2O, H+ (H2SO4)

mechanism

Answer 6

Pi bond attacks H+/
Carbocation created/
H2O attacks carbocation, O is +/
H-O bond attacks O+

Question 7

hydroboration-oxidation; reagents

Answer 7

BH3, THF

H2O2, NaOH, H2O

Question 8

BH3, THF

H2O2, NaOH, H2O

Answer 8

OH attacks less sub/
H attacks more sub/
syn addition

Question 9

X2

Answer 9

anti addition of 2 X’s

Question 10

X2

mechanism

Answer 10

X-X bond broken, X leaves/
Other X forms triangle thing with the C’s/
First X attacks one C, triangle broken

Question 11

halohydrin; reagents

Answer 11

X2,

H2O

Question 12

X2

H2O

Answer 12

anti addition of OH-X/
OH on more sub/
X on less sub

Question 13

X2

Nu

Answer 13

anti addition of Nu-X/
Nu on more sub/
X on less sub

eg Cl2, CH3OH

Question 14

X2
H2O/Nu
mechanism

Answer 14

X-X bond broken, X leaves/
Other X forms triangle thing with the C’s/
H2O (Nu) attacks one C, triangle broken, attacks the more pos (most branched C)

Question 15

epoxides; reagents

Answer 15

ROCOOH

Question 16

ROCOOH

Answer 16

makes O triangle thing

Question 17

NaNH2

R-X

Answer 17

alkene –> alkyne

Question 18

NaNH2
R-X
mechanism

Answer 18

Makes C-H into C- and Na+/

Add the R part of R-X to the C-

Question 19

hydrogenation of alkynes; reagents

Answer 19

H2

Lindlar catalyst

Question 20

H2

Lindlar catalyst

Answer 20

alkyne –> cis alkene

Question 21

catalytic hydrogenation; reagents

Answer 21

H2, metal (Pd/Ni/Pt)

Question 22

dissolving metal reduction alkynes; reagents

Answer 22

alkali metal (Li/Na/K), NH3

Question 23

dissolving metal reduction alkynes

Answer 23

alkynes –> trans alkenes

Question 24

osmium

Answer 24

adds 2 OH’s syn

Question 25

osmium reagents

Answer 25

OsO4, SH2/Na2SO3