synthetic rxns opposite

Question 1

alkene to markov addition of H and OH

Answer 1

1) Hg(OAc)2, H2O, THF

2) NaBH4

Question 2

alkene toMarkov addition of H and OR

R can be any alkyl or H

Answer 2

1) Hg(OAc)2, HOR, THF

2) NaBH4

Question 3

alkene to Anti mark OH and H

Answer 3

1) BH3, THF,

2) H2O2, NaOH, H2O

Question 4

alkene to Anti mark add of X and H
(X= Br, Cl, I)
ANtimark add of Br

Answer 4

HX and peroxide, light and heat
(ex: HBr and peroxide w/ light and heat)
(Peroxide = ROOR ex H2O2)

Question 5

alkene to Markov add of H and X

ex: Mark add of Br and H

Answer 5

HX, no peroxide, cold, dark

Ex: HBr w/ no peroxide, cold dark

Question 6

alkene Epoxide ring

Answer 6

MCPBA

or proxy acid can do this too

Question 7

H added to the O on epoxide ring

Answer 7

acid conditions (H3O+)

Question 8

epoxide ring to Antimarkov OR

Answer 8

1)strong base RO- or R2N- or R- (R= h or alkyl)
2) diluted acid
opens up ring to most sub C becomes OH
OR adds to least sub C from the top pushing H down
Cis CH3 and OR
Cis H and OH( OH under most sub C)

Question 9

epoxide ring to markov add of OR

Answer 9

H3O+ and HOR
(HOR can = water or any alkyl)
ring opens to least sub C
OR adds on to back of most sub C pushing group down

Question 10

alkene Markov add of Br and OR

ex: br and oh

Answer 10

Br2 and HOR

Br added first to form bromonium ring
breaks opening to least sub C
OR( OH) out competes second Br adds to back side

Question 11

alkene to Trans Br2

trans X

Answer 11

Br2
forms bromonium ring
second Br added to backside of as ring breaks
forms trans not cis

Question 12

alkene to cycopropane ring, carbene to alkene

Answer 12

CHCl3 and KOH
or
CH2I2, Zn(Cu)

Question 13

alkene to syn antimarkov OH and H

trans to CH3

Answer 13

1) BH3, THF

2) H2O2, NaOH, H2O

Question 14

alkene to syn added H’s

push original groups on carbon to trans

Answer 14

H2 and Pd or Pt

Question 15

Alkyne to alkane

Answer 15

H2 and Pd or Pt metal

Question 16

Alkyne to cis alkene

H’s on same side

Answer 16

H2 Ni2B
or
H2 and lindlar catalyst

Question 17

alkyne to trans alkene

Answer 17

Na and NH3

Question 18

1* alcohol to aldehyde

Answer 18

PCC

Question 19

2* alcohol to Ketone

4 things do this

Answer 19

KMnO4
or
Na2Cr2O7, Acid(H2SO4 or H3O+) , H20
or
CrO3, acid, water
or 
PCC

Question 20

Carboxylic acid from 1* alcohol

Answer 20

1)PCC 2) KMnO4 or Na2Cr2O7, acid, water or CrO3, acid, water ( this will stop it at an aldehyde then to a carboxylic acid
or
KMnO4 or Na2Cr2O7, acid, water or CrO3, acid, water
(will take you straight, no stop)

Question 21

Aldehyde to carboxylic acid

Answer 21

KMnO4
or Na2Cr2O7, acid, water
or CrO3, acid, water

Question 22

syn addition of 2 OH breaking pi bond

trans already present groups

Answer 22

1) OsO4

2) H2O2 or NaHSO4

Question 23

Alkene to 2 split groups each with a capped =O

Ketone and aldehyde

Answer 23

1) O3

2) Zn, acetic acid

Question 24

Alkene to 2 split groups capped with =O each

H on carbons oxidized

Answer 24

1) KMnO4 Hot!

2) H30+ and H2O

Question 25

1) alkyne to alkene with Markov add of H X

2) alkene with X on most sub to alkane with Markov add of 2nd X and H to most sub C again

Answer 25

1) HX cold, dark, no peroxide (one molar)
2) HX cold dark no peroxide (excess)

x= Br, Cl, or I

Question 26

1) alkyne to trans add of X to each carbon

2) alkene with trans X’s to alkane with twin trans X’s

Answer 26

1) X2 ( one molar)

2) X2 (excess)

Question 27

Tautomerization
double bond moves from C=C to C=O
H from Oh moves to fill C octet

Enol( = and OH present) to Keto( either aldehyde, ketone)

Answer 27

tautomerization
or 
D3O+ 
(this is automatic when enroll is present
enol to keto)

Question 28

alkyne to Keto( aldehyde, Ketone, carboxylic acid)

Mark h2o added to alkyn

Answer 28

H2O, H2SO4, HgSO4

Question 29

Alkyne to R-C-C=O

Anti mark of h2o added to alkyn with tauto

Answer 29

1) BH3, THF

2) H2O2, NaOH, H2O

Question 30

Alkyne to alkyne with C losing an H and being deprotonated to C- or C: (which is C-)

Answer 30

NaNH2

or Na+ and -NH2

Question 31

RCN (CN has triple bond) to R-C(=O)NH2

Answer 31

H20, H2SO4

Question 32

H3O+ h2o

Answer 32

Markov oh but after rearrangement