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Last updated 5:01 PM on 6/30/26
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6 Terms

1
New cards

HX (X= Cl, Br, I)

  • intermediate

    • carbocation

  • rearrange?

    • yes

  • stereoselectivity

    • random

  • regioselectivity (where does H/electrophile add? Markovnikov/anti or not selective)

    • markovnikov to give the more stable carbocation

  • functional group of the products that form

    • alkyl halides which can go on to do nucleophilic substitution

2
New cards

H2SO4/H2O

  • intermediate

    • carbocation

  • rearrange?

    • yes

  • stereoselectivity

    • random

  • regioselectivity (where does H/electrophile add? Markovnikov/anti or not selective)

    • markovnikov to give the more stable carbocation

  • functional group of the products that form

    • alcohol

3
New cards

  1. Hg(OAc)2, ROH

  2. NaBH4

  • intermediate

    • bridged

  • rearrange?

    • no

  • stereoselectivity

    • anti because bridged

  • regioselectivity (where does H/electrophile add? Markovnikov/anti or not selective)

    • markovnikov

  • functional group of the products that form

    • alcohol/ether

4
New cards

  1. BH3

  2. H2O2, NaOH, H2O

  • intermediate

    • syn addition

  • rearrange?

    • no

  • stereoselectivity

    • syn

  • regioselectivity (where does H/electrophile add? Markovnikov/anti or not selective)

    • anti markov.

  • functional group of the products that form

    • alcohol/ether

5
New cards

X2/CH2Cl2 X = Cl, Br, I

  • intermediate

    • bridged

  • rearrange?

    • no

  • stereoselectivity

    • anti

  • regioselectivity (where does H/electrophile add? Markovnikov/anti or not selective)

    • NA

  • functional group of the products that form

    • dihalide

6
New cards

X2/H2O (X = Cl, Br, I)

  • intermediate

  • rearrange?

    • No

  • stereoselectivity

    • anti

  • regioselectivity (where does H/electrophile add? Markovnikov/anti or not selective)

    • N/A

  • functional group of the products that form

    • halohydrin