Which compound reacts with CH3CH2OH in the presence of an acid catalyst to give

Question

Which compound reacts with CH3CH2OH in the presence of an acid catalyst to give the compound CH3CH2CH2CO2CH2CH3? 1. CH3CH2CH2CH2Br 2. CH3CH2COCH3 3. CH3CH=CHCOH 4. CH3CH2CH2COH 5. CH3CH2CH2COOH I wasn't sure how to draw the double bonds between the oxygen and their corresponding carbons, but I think it is pretty self-explanatory as there are no charges. Thanks!!!

Explanation / Answer

this is the reaction...and it's called an "esterification" reaction ....O....... ....... ...... ...... ....O ....||...... ...... ....... ...... .......|| R-C-OH + HO-R' ----> R-C-OR' + H2O ...... ....?... .??... .... .... .... ... .... .... ...? ... .these three combine to form... . this your reaction... ....... ....... ....... ..O ..... ..... ...... ..... .|| CH3-CH2-CH2-C-O-CH2-CH3 is formed by what + HO-CH2-CH3 ???? answer is ....... ....... ....... ..O ..... ..... ...... ..... .|| CH3-CH2-CH2-C-O-H... butyric acid ************ ....... ....... ....... ..O ..... ..... ...... ..... .|| CH3-CH2-CH2-C-O-Cl.. doesn't exist but this does ....... ....... ....... ..O ..... ..... ...... ..... .|| CH3-CH2-CH2-C-Cl.. and this is an acyl chloride and that can react with ethanol to form the ethyl butanoate product. However this reaction is usually run in basic conditions to neutralize the resulting HCl and drive the reaction to completion.

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