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Addition of Br 2 , Diols, and Cleavage of a double bond

Addition of Br 2 , Diols, and Cleavage of a double bond. Addition of Bromine. Bromine adds across a double bond in a trans- fashion. Creates a “bromonium” ion as an intermediate with two bonds to two different carbons, one longer than the other. Mechanism (Addition of Br 2 ).

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Addition of Br 2 , Diols, and Cleavage of a double bond

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  1. Addition of Br2, Diols, and Cleavage of a double bond

  2. Addition of Bromine Bromine adds across a double bond in a trans-fashion. Creates a “bromonium” ion as an intermediate with two bonds to two different carbons, one longer than the other.

  3. Mechanism (Addition of Br2)

  4. Addition of a cis-diol A cis-diol is a diol where both –OH groups are pointing in the same direction. There are two ways to create a diol, with either osmium tetroxide (OsO4) or cold, dilute permangante (KMnO4).

  5. Cis-Diols

  6. Cleavage of Double Bond Double bonds are cleaved by either warm, concentrated KMnO4 and Ozone (O3). The ends are left as either ketones, aldehydes or carboxylic acids.

  7. Double Bond Cleavage • Note that in cyclic alkenes, the bond breaks and turns into a straight chain aldehyde and ketone.

  8. What is the product of the following reaction?

  9. Incorrect Try Again

  10. Correct!

  11. What is the product of the following reaction?

  12. Incorrect Try Again

  13. Correct!

  14. What is the product of the following reaction?

  15. Incorrect Try Again

  16. Correct!

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