Methyl acetate (CH;COOCH3) is formed by the reaction of acetic acid with methyl alcohol. If the methyl alcohol is labeled with oxygen-18, the oxygen-18 ends up in the methyl acetate: CH;COH + HSOCH3 CH;Č18OCH3 + H,O (a) Do the C-OH bond of the acid and the O-H bond of the alcohol break in the reaction, or do the O-H bond of the acid and the C-OH bond of the alcohol break? (b) Imagine a similar experiment using the radioisotope H, which is called tritium and is usually denoted T. Would the reaction between CH;COOH and TOCH; provide the same information about which bond is broken as does the above experiment with Hl$OCH;?

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Methyl acetate (CH;COOCH3) is formed by the reaction
of acetic acid with methyl alcohol. If the methyl alcohol
is labeled with oxygen-18, the oxygen-18 ends up in the
methyl acetate:
CH;COH + HSOCH3
CH;Č18OCH3 + H,O
(a) Do the C-OH bond of the acid and the O-H bond
of the alcohol break in the reaction, or do the O-H bond
of the acid and the C-OH bond of the alcohol break?
(b) Imagine a similar experiment using the radioisotope H,
which is called tritium and is usually denoted T. Would the
reaction between CH;COOH and TOCH; provide the same
information about which bond is broken as does the above
experiment with Hl$OCH;?
Transcribed Image Text:Methyl acetate (CH;COOCH3) is formed by the reaction of acetic acid with methyl alcohol. If the methyl alcohol is labeled with oxygen-18, the oxygen-18 ends up in the methyl acetate: CH;COH + HSOCH3 CH;Č18OCH3 + H,O (a) Do the C-OH bond of the acid and the O-H bond of the alcohol break in the reaction, or do the O-H bond of the acid and the C-OH bond of the alcohol break? (b) Imagine a similar experiment using the radioisotope H, which is called tritium and is usually denoted T. Would the reaction between CH;COOH and TOCH; provide the same information about which bond is broken as does the above experiment with Hl$OCH;?
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