organic chem chapter 10 reagents

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Last updated 6:34 AM on 7/29/26
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12 Terms

1
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HCl

  • carbocation echanism

  • has rearrangement

  • markovnikov alkyl chloride as major product

  • neither syn nor anti stereochemistry

PUT THE CL ON THE MORE SUBSTITUTED CARBON

2
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HBr

  • carbocation mechanism

  • has rearrangement

  • markovnikov alkyl bromide as major product

  • neither syn nor anti stereochemistry

PUT BR ON THE MORE SUBSTITUTED CARBON

3
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HI

  • carbocation mechanism

  • has rearrangement

  • markovnikov alkyl iodide as makor product

  • neither syn nor anti stereochemistry

PUT I ON THE MORE SUBSTITUTED CARBON

4
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H2O/H2SO4 (or H3O+)

  • carbocation mechanism

  • has rearrangement

  • markovnikov alcohol as major product

  • neither syn nor anti stereochemistry

REPLACE THE DOUBLE BOND WITH AN OH

5
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ROH/H2SO4

  • carbocation mechanism

  • has rearrangement

  • markovnikov ether as major product

  • neither syn nor anti stereochemistry

REPLACE THE DOUBLE BOND WITH AN OR

6
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Hg(OAc)2, H2O NaBH4

  • mercurinium ion as mechanism

  • no rearrangement

  • markovnikov alcohol as major product

  • anti stereochemistry

7
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1) BH3THF 2) H2O2, OH-

  • concerted mechanism (like sn2)

  • no rearrangement

  • anti-markovnikov alcohol as major product

  • syn stereochemistry

OH GOES TO THE LESS SUBSTITUTED CARBON

8
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Br2/CH2Cl2

  • mechanism creates a bromonium ion

  • no rearranement

  • vicinal dibromide as major product

  • anti stereochemistry

ERASE THE DOUBLE BOND AND ADD BR TO BOTH CARBONS

9
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Cl2/CH2Cl2

  • mechanism creates a chloronium ion

  • no rearrangement

  • vicinal dichloride as major product

  • anti stereochemistry

ERASE THE DOUBLE BOND AND ADD CL TO BOTH CARBONS

10
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Br2/H2O

  • mechanism creates a bromonium ion

  • no rearrangement

  • markovnikov halohydrin (halogen and OH) as major product

  • anti stereochemistry

ERASE THE DOUBLE BOND AND ADD BR AND OH

(SAME WITH CL2/H2O)

11
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HBr + ROOR

  • mechanism creates a radical

  • no rearrangement

  • anti-markovnikov alkyl bromide as major product

  • not stereospecific

PEROXIDES FLIP THINGS

12
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H2, Pd/C/Pt/Ni

  • catalytic mechanism

  • no rearrangement

  • alkane as major product

  • syn stereochemistry

THINK ERASE THE DOUBLE BOND