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Flashcards in synthetic rxns opposite Deck (32)
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1

alkene to markov addition of H and OH

1)Hg(OAc)2, H2O, THF
2) NaBH4

2

alkene toMarkov addition of H and OR
(R can be any alkyl or H)

1)Hg(OAc)2, HOR, THF
2) NaBH4

3

alkene to Anti mark OH and H

1)BH3, THF,
2) H2O2, NaOH, H2O

4

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

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

5

alkene to Markov add of H and X
(ex: Mark add of Br and H)

HX, no peroxide, cold, dark
(Ex: HBr w/ no peroxide, cold dark)

6

alkene Epoxide ring

MCPBA
( or proxy acid can do this too)

7

H added to the O on epoxide ring

acid conditions (H3O+)

8

epoxide ring to Antimarkov OR

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)

9

epoxide ring to markov add of OR

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

10

alkene Markov add of Br and OR
(ex: br and oh)

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

11

alkene to Trans Br2
(trans X)

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

12

alkene to cycopropane ring, carbene to alkene

CHCl3 and KOH
or
CH2I2, Zn(Cu)

13

alkene to syn antimarkov OH and H
trans to CH3

1) BH3, THF
2) H2O2, NaOH, H2O

14

alkene to syn added H's
push original groups on carbon to trans

H2 and Pd or Pt

15

Alkyne to alkane

H2 and Pd or Pt metal

16

Alkyne to cis alkene
H's on same side

H2 Ni2B
or
H2 and lindlar catalyst

17

alkyne to trans alkene

Na and NH3

18

1* alcohol to aldehyde

PCC

19

2* alcohol to Ketone
(4 things do this)

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

20

Carboxylic acid from 1* alcohol

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)

21

Aldehyde to carboxylic acid

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

22

syn addition of 2 OH breaking pi bond
trans already present groups

1) OsO4
2) H2O2 or NaHSO4

23

Alkene to 2 split groups each with a capped =O
(Ketone and aldehyde)

1) O3
2) Zn, acetic acid

24

Alkene to 2 split groups capped with =O each
H on carbons oxidized

1) KMnO4 Hot!
2) H30+ and H2O

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

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

x= Br, Cl, or I

26

1)alkyne to trans add of X to each carbon
2) alkene with trans X's to alkane with twin trans X's

1) X2 ( one molar)
2) X2 (excess)

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)

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

28

alkyne to Keto( aldehyde, Ketone, carboxylic acid)
Mark h2o added to alkyn

H2O, H2SO4, HgSO4

29

Alkyne to R-C-C=O
Anti mark of h2o added to alkyn with tauto

1) BH3, THF
2) H2O2, NaOH, H2O

30

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

NaNH2
or Na+ and -NH2