Alkene Reactions

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14 Terms

1
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When reacting with H-Br, what are the two groups that you get? Which side? Stereochemistry? Regiochemistry?

You get H and Br.

H adds to the side with more H’s on it.

2 syn + 2 anti

Look for cation rearrangements.

2
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When reacting with dilute H3O+, what are the two groups that you get? Which side? Stereochemistry?

You get H and OH.

H adds to the side with more H’s on it.

2 syn + 2 anti

Look for cation rearrangements.

3
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When reacting with H-Br with ROOR, what are the two groups that you get? Which side? Stereochemistry?

You get H and Br.

H adds to the side with least H’s on it.

2 syn + 2 anti

There are no cation rearrangements.

4
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When reacting with 1. Hg(OAc)2, HOH with 2. NaBH4, what are the two groups that you get? Which side? Stereochemistry?

You get H and OH.

H adds to the side with more H’s on it.

2 syn + 2 anti

There are no cation rearrangements.

5
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When reacting with 1. BH3 THF with 2. NaOH, HOOH, what are the two groups that you get? Which side? Stereochemistry?

You get H and OH.

H adds to the side with least H’s on it.

2 syn

There are no cation rearrangements.

6
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When reacting with H2, what are the two groups that you get? Which side? Stereochemistry?

You get H and H.

No regio chemistry.

2 syn

No carbocation rearrangements.

7
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When reacting with Br2, what are the two groups that you get? Which side? Stereochemistry?

You get Br and Br.

No regio chemistry.

2 anti

No carbocation rearrangements.

8
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When reacting with mCPBA/ peroxyacids, what are the two groups that you get? Which side? Stereochemistry?

You get a ring with O.

No regional chemistry.

No carbocation rearrangements.

9
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When reacting with mCPBA/peroxyacids under acidic conditions, what are the two groups that you get? What about with an alcohol? Which side? Stereochemistry? (ring opening under acidic conditions)

For H3O+ You get OH and OH, the second water adding to the side with less H’s.

For H3O+ with an alcohol, you get OH and OR, the OR group adding to the side with less H’s.

2 anti

No carbocation rearrangements.

10
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When reacting with mCPBA/peroxyacids under basic conditions, what are the two groups that you get? What about with an alcohol? Which side? Stereochemistry? (ring opening under basic conditions)

With just a base (NaOH) You get OH and OH.

The OH adds to the side with more H’s.


With a base and an alcohol, you get OH and OR.

The OR group adds to the side with more H’s.


2 anti

No carbocation rearrangements.

11
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When reacting with OsO4 with NMO or NaHSO3, what are the two groups that you get? Which side? Stereochemistry?

You get OH and OH.

2 syn

No carbocation rearrangements

12
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When reacting with cold KMnO4 with NaOH, what are the two groups that you get? Which side? Stereochemistry?

You get OH and OH.

2 syn

No carbonation rearrangements.

13
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When reacting with rt KMnO4, what are the two groups that you get? Which side? Stereochemistry?

They separate the double bond and instead connect to Oxygen.

One side, when you get a ketone stop. On the other, you get an aldehyde. Add another oxygen to turn it into Carboxylic acid.

14
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When reacting with O3 with Zn or DMS, what are the two groups that you get? Which side? Stereochemistry?

They separate the double bond and instead connect to Oxygen. Stop there.