Term
| purpose of E12: alcohols as nucleophiles |
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Definition
| produce an ester through nucleophilic substitution |
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Term
| E12: alcohols as nucleophiles overall reaction |
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Definition
| 1-butanol + acetic acid = butyl acetate |
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Term
| E12: which layer is on bottom |
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Definition
| water b/c butyl acetate is less dense |
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Term
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Definition
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Term
| IR range for carboxylic acid |
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Definition
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Term
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Definition
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Term
| E12: why alcohols can be nucleophilic |
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Definition
- lone pairs on oxygen
- attack electron-deficient atom (usually C in C=O bond) |
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Term
| E12: when alcohols react with carbonyl groups of carboxylic acids... |
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Definition
| ...a nucleophilic substitution occurs, in which the alcohol replaces the OH of the carboxylic acid, producing an ester |
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Term
| E12: two strategies for overcoming limitations in equilibria in synthesis |
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Definition
- use one reactant in excess
- remove product as it is produced |
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Term
| E12: why does the acid remain in the flask |
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Definition
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Term
| E12: why does the acid remain in the flask |
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Definition
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Term
| potassium permanganate test |
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Definition
positive = stays purple, no C=C
negative = changes to brown, precipitate, C=C |
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Term
| Williamson synthesis goes through a _____ reaction |
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Definition
| Sn2 between a good nucleophile and a suitably alkyl halide |
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Term
| Williamson ether: which is nucleophile and which is alkyl halide? |
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Definition
phenoxide ion (ArO-) is nucleophile
methyl iodide is alkyl halide |
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Term
| role of PTC in Williamson ether synthesis |
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Definition
- to transfer the phenoxide ion from the aqueous phase into the organic phase where the Sn2 reaction occurs
- after the first NaOH solution is added, two layers are formed, with CH3I on bottom and NaOH on top
o two layers are not miscible, so the ArO- will not come into contact with the CH3I, meaning the reaction won’t happen
o the PTC has dual solubility
• soluble in organic layer because of 4 butyl groups
• soluble in aqueous layer because of ionic character |
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Term
| purpose of Williamson ether synthesis |
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Definition
| synthesize an ether, using an Sn2 reaction, and then purify the product using chromatography column with silica gel. The reactant is 4-ethylphenol and tetrabutylammonium bromide and methyl iodide catalyst and react with it, respectively, forming methyl p-ethylphenyl ether. Then characterize by IR. |
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Term
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Definition
- based on polarities
- silica gel is polar & keeps polar molecules
- nonpolar molecules pass through |
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Term
| in Williamson ether synthesis, name 4 potential nucleophiles |
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Definition
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