reagents

Question 1

TsCl , Py or NEt3

Answer 1

good leaving group, doesnt invert chirality center

Question 2

MCPBA

Answer 2

conver alkene to an epoxide, syn

Question 3

HBr

Answer 3

SN1 mostly for converting OH to halide

protonates OH first to make water that leaves

Question 4

NaOH

Answer 4

strong base so E2, favors zaitsev product (more substituted alkene)

Question 5

tBuOK

Answer 5

E1, non Nuc base, bulky so favor hoffman product

Question 6

NaH

Answer 6

E2 reaction
base, so will eliminate beta H to create alkene
also can use to deprotonate OH groups and then make the OH group thing now a base to add to stuff

Question 7

conc H2SO4 (hot)
(start with OH group)

Answer 7

E1 elimination, because protic solvent,

usually to convert OH to alkene because first protonate OH and then water will remove beta H to get alkene

Question 8

H3O+ (start with alkene)

Answer 8

adds OH to the alkene, usually markovnikov addition

Question 9

Br2 H2O

Answer 9

brominium ion intermediate is formed, it gets water will attack the more substitured

Question 10

1) O3

2) DMS or Zn HOAc

Answer 10

will take the double bond and break to create carbonyls

Question 11

1) OsO4

2) NaHSO4

Answer 11

syn addition of 2 OH to alkene

+ Enantiomer

Question 12

KMnO4, NaOH cold dilute

Answer 12

syn addition of 2 OH to alkene

+ Enantiomer

Question 13

1) RCO3H

2) H3O+

Answer 13

epoxide formed

anti addition of 2 OH

Question 14

H2, Pt

Answer 14

syn addition

full reduction of alkyne to alkane or alkene to alkane

Question 15

1) BH3*THF

2) H2O2, NaOH

Answer 15

syn addition of H and OH to an alkene
antimarkovnikov
+ En

Question 16

1) Hg(OAc)2, H2O

2) NaBH2

Answer 16

alkene to alcohol

markovnikov addition

Question 17

xs HX

Answer 17

converts alkyne to dihalide

Question 18

1) xs NaNH2

2) H2O

Answer 18

converts dihalides to alkynes

water is there to protonate the alkyne again because the NH2 could keep deprotonating it

Question 19

H2, Lindlar

Answer 19

only can reduce alkyne to Z alkene (cis)

Question 20

Na NH3 (l)

Answer 20

alkyne to E alkene (Z)

Question 21

HgSO4, H2SO4 H2O

Answer 21

alkyne to ketone with a methyl at one end (other end would be what ever what originally at the other end of the alkyne)

Question 22

1) R2BH or BH3

2) H2O2, NaOH

Answer 22

alkyne to ketone but one end is H (other end would be what ever what originally at the other end of the alkyne)

Question 23

xs X2, CCl4

Answer 23

alkyne to alkane with 4 halides attached

Question 24

i equiv. X2, CCl4

Answer 24

E alkene (trans) with 2 halides attached

Question 25

Br2, ROOR

Answer 25

radical mechanisms

Br radical will rip off H, pi bond wont do anything in this reaction

Question 26

HBr, ROOR

Answer 26

radical mechanism

pi bond reactions with Br radical

Question 27

Cl2 heat/ hv

Answer 27

not as selective, eveything is made

Question 28

Br2 heat/hv

Answer 28

selective because slower reaction