Chemistry Reactions

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21 Terms

1
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  1. Br2, CH2Cl2


Halogenation


anti-addition of two Br’s


2
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  1. Br2/Cl2, H2O

OR

  1. NBS, H2O, DMSO


Halohydrins


anti-addition of OH and Br, follows Markov

3
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  1. H3O+, THF

OR

  1. Hg(OAc)2, H2O

  2. NaBH4


acid-catalyzed hydration

oxy-mercuration hydration

addition of H& OH, follows Markov, no stereochemistry

4
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  1. BH3, THF

  2. H2O2, OH-


hydroboration

syn-addition of H & OH, anti-Markov

5
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H2, PtO2/Pd/C’


hydrogenation [reduction]

alkane restored

6
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  1. MCPBA, CH2Cl2

OR

  1. Cl2, H2O ← halohydrin

  2. OH-, H2O


epoxidation [oxidation]

syn-addition of an epoxide (3 membered oxygen ring)

7
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  1. MCPBA, CH2Cl2

  2. H3O+, THF


hydroxylation [oxidation]

trans-1,2-diol

8
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  1. OsO4, pyridine

  2. NaHSO3


hydroxylation [oxidation]

cis-1,2-diol

9
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  1. OsO4, acetone/H2O

  2. NMO


hydroxylation [oxidation]

cis-1,2-diol + OsO4 recovered

10
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  1. O3, CH2Cl2, -78

  2. Zn, H3O+

OR

  1. OsO4, NMO ← cis-1,2-diol

  2. HIO4, H2O, THF


ozonolysis [oxidation]

carbonyl groups formed

11
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  1. KMnO4, H2O


cleavage [oxidation]

carbonyl, carboxylic acid, and carbon dioxide possibilites

12
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  1. CHCl3, KOH


carbene addition

syn-addition of 3-membered carbon ring with two trans Cl’s

13
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  1. CH2I2, Zn(Cu)


carbene addition

syn-addition of 3-membered carbon ring

14
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  1. 1,2-dihalogenated alkane + 2eq. KOH, EtOH


generation of alkyne

15
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  1. 2eq. HBr/HCl, CH3CO2H


electrophilic addition of alkyne

anti 1,1 dihalogenated alkane (halogens on same carbon)

16
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  1. alkyne, 2eq. Br2/Cl2, CH2Cl2


halogenation

1 eq. only gives 1,2 halogen alkene

anti addition of four Br’s (1,1,2,2)

17
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  1. HgSO4, H3O+

enol intermediate (C=C-OH) to ketone only


mercury-catalyzed hydration


Addition of OH & H to alkyne, follows Markov, no stereochemistry

18
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  1. 2 eq. BH3, THF

  2. H2O2, OH-

enol intermediate to ketone or aldehyde

hydroboration


addition of OH & H to alkyne, anti-markov

19
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  1. H2, Pd/C or PtO2


hydrogenation [reduction]

alkane restored from alkyne

20
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  1. H2, lindlar catalyst


hydrogenation [reduction]


(syn) cis-alkene restored from alkyne

21
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  1. Li, NH3


hydrogenation [reduction]


(anti) trans-alkene restored from alkyne