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Alkohol, Epoxides, Dehydrohalogenation, Nucleophilic Subsitution,…
Alkohol
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Alkyne
- Alkynes contain a triple bond.
- Removal of two molecules of HX from a vicinal or
geminal dihalide produces an alkyne, called dehydrohalogenation
Alkyl Halides
When alcohols react with a hydrogen halide, a substitution takes place producing an alkyl halide and water
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- The order of reactivity of alcohols is 3° > 2° > 1° methyl.
- The order of reactivity of the hydrogen halides is HI > HBr > HCl (HF is generally unreactive).
- The reaction is acid catalyzed.
- Alcohols react with the strongly acidic hydrogen halides HCl, HBr, and HI, but they do not react with nonacidic NaCl, NaBr, or NaI.
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Ether
An ester is an organic compound that is a derivative of a carboxylic acid in which the hydrogen atom of the hydroxyl group has been replaced with an alkyl group. The structure is the product of a carboxylic acid (the R -portion) and an alcohol (the R′ -portion).
Nomenclature
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The more complex alkyl group is the alkane name. The small group (with the oxygen) becomes an "alkoxy" group.
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Alkane
Halogenation
R-H + X2, heat or hv ------> R-X + HX
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a) heat or light required for reaction. b) X2: Cl2 > Br2 I2 c) yields mixtures d) H: 3o > 2o > 1o > CH4 e) bromine is more selective
Epoxides
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- peroxyacid use to convert alkene to epoxides
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- epoxides are much more reactive than ethers in nucleophilic substitution reactions because the strain in their three-membered ring is
relieved when the ring opens
Dehydrohalogenation
- Alkenes can be obtained from haloalkanes (alkyl halides)
- If two alkenes may be formed due to dehydrohalogenation of a haloalkane, the one which is most substituted is the main product.
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- diethyl ether or ethyl ether
- t-butyl methyl ether or methyl t-butyl ether
- 2-Methyl-2-methoxypropane
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- This method involves an SN2 attack of the alkoxide on an unhindered primary halide or tosylate.
- The alkoxide is commonly made by adding Na, K, or NaH to the alcohol.
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