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9 Cards in this Set
- Front
- Back
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alcohols:
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compounds whose molecules have a hydroxyl group (OH) attached to a saturated carbon.
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ethers:
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O atom is bonded to 2 C atoms
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nomenclature of alcohols:
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1. longest chain to which the OH is attached gives us the base name
- ending is ol. 2. # the longest chain from the end that gives the C bearing hydroxyl group the lowest # notes: OH has precedence over double and triple bonds common names for alcohols is alkyl alcohol such as methyl alcohol... etc. |
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Nomenclature for ethers:
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1. ethers are frequently given common functional class names
--- listed in alphabetical order both groups that are attached to the O atom and adds the word ether at the end (ex. ethyl methyl ether) 2. IUPAC: ethers are named as alkoxyalkanes, alkoxyalkenes and alkoxyarenes. The RO- group is the alkoxy group (ex:20methoxypentane) 3. cyclic ethers: - use replacement nomenclature in which we relate the cyclic ether to the corresponding hydrocarbon ring system and use the prefix oxa- to indicate that an O atom replaces a CH2 group (ex: oxacyclopropane) |
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are ethers soluble in water?
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yes due to H-bonding
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as alcohols increase in size do they become less or more soluble in water?
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less due to the hydrocarbon portion of the molecule length, long chain alcohols are more "alkane-like".
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acid-catalyzed hydration of alkenes:
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- markovnikov regioselectivity
- reaction is reversible - has limited synthetic utility b/c the carbocation intermidate may rearrange if a more stable or isoenergetic carbocation is possible by hydride or alkanide migration. |
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oxymercuration-demercuration:
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- alkenes react w/ mercuric acetate in a mixture of water and tetrahydrofuran (THF) to produce (hydroxyalkyl)mercury compounds, which can be reduced to alcohols w/ sodium borohydride and water
- markovnikov regioselectivity - generally takes place w/o the complication of rearrangements - is not stereoselective b/c even though the oxymercuration step occurs w/ anti-addition, the demercuration step is not stereoselective (mixture produced) |
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hydroboration- oxidation:
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1. alkene reacts w/ BH3: THF or dibroane to produce an alkylborane.
2. oxidation and hydrolysis of the alkylborane w/ hydrogen peroxide and base yield an alcohol 3. B and H undergo syn addition to the alkene, treatment w/ hydrogen peroxide and base replaces the B w/ OH w/ retention of config. net addition of H and OH occurs w/ anti-markovnikov regioselectivity and syn steroselectivity |
