Term
| A __________ is an alcohol with a halogen on the adjacent carbon atom. |
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Definition
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Term
In the presence of water, halogens add to alkenes to form __________.
The electrophilic halogen adds to the alkene to give a __________ ion, which is also electrophilic.
__________ acts as a nucleophile to open the __________ ion and form the halohydrin. |
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Definition
1) Halohydrins
2) Halonium
3) Water
4) Halonium |
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Term
*Mechanism 8-8: Formation of Halohydrins*
Step 1: Electrophilic attack forms a __________ ion.
Step 2: __________ opens the halonium ion; deprotonation gives the __________. |
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Definition
1) Halonium
2) Water
3) Halohydrin |
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Term
| When halogenation takes place with no solvent or with an inert solvent such as __________ __________ or __________, only the __________ ion is available as a nucleophile to attack the halonium ion; the product is a __________. |
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Definition
1) Carbon tetrachloride
2) Chloroform
3) Halide
4) Diihalide |
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Term
When an alkene reacts with a halogen in the presence of a nucleophilic solvent such as __________, a solvent molecule is the most likely nucleophile to attack the __________ ion.
When a __________ molecule attacks the __________ ion, the final product is a halohydrin, with a __________ on one carbon atom and a __________ group on the adjacent carbon atom. |
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Definition
1) Water
2) Halonium
3) Water
4) Halonium
5) Halogen
6) Hydroxyl |
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Term
Stereochemistry of Halohydrin Formation:
Since the mechanism involves a __________ ion, stereochemistry of addition is __________, as in halogenation. |
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Definition
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Term
Orientation of Halohydrin Formation:
Even though a __________ ion is involved instead of a carbocation, the extended version of __________ __________ applies to halohydrin formation.
When propene react with chlorine water, the major product has the electrophile (the __________ atom) bonded to the (less/more) substituted carbon of the double bond with the nucleophile (the __________ group) bonded to the (less/more) substituted carbon. |
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Definition
1) Halonium
2) Markovnikov's Rule
3) Chlorine
4) Less
5) Hydroxyl
6) More |
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Term
The __________ orientation observed in halohydrin formation is explained by the structure of the __________ ion intermediate.
The two carbon atoms bonded to the halogen have partial __________ charges, with a larger charge (and a __________ bond to the halogen) on the (less/more) substituted carbon atom.
The nucleophile (__________) attacks this more substituted, more electrophilic carbon atom, producing a result of both __________ stereochemistry and __________ orientation. |
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Definition
1) Markovnikov
2) Halonium
3) Positive
4) Weaker
5) More
6) Water
7) Anti
8) Markovnikov |
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