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$OCH;?
Methyl acetate (CH;COOCH3) is formed by the reaction of acetic acid with methyl alcohol. If the methyl alcohol is labeled with oxygen-18, the oxygen-18 ends up in the methyl acetate: CH;COH + HSOCH3 CH;Č18OCH3 + H,O (a) Do the C-OH bond of the acid and the O-H bond of the alcohol break in the reaction, or do the O-H bond of the acid and the C-OH bond of the alcohol break? (b) Imagine a similar experiment using the radioisotope H, which is called tritium and is usually denoted T. Would the reaction between CH;COOH and TOCH; provide the same information about which bond is broken as does the above experiment with Hl$OCH;?
Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter10: Organic Chemistry
Section: Chapter Questions
Problem 10.57P: Aspirin is prepared by the reaction of salicylic- acid with acetic anhydride as shown in the...
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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$OCH;?](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F8a4e5106-9880-4867-a0ca-754fd95ceb44%2F7df43a07-cadd-4365-aa19-84f68ee78aa4%2F7vxspfo.png&w=3840&q=75)
Transcribed Image Text:Methyl acetate (CH;COOCH3) is formed by the reaction
of acetic acid with methyl alcohol. If the methyl alcohol
is labeled with oxygen-18, the oxygen-18 ends up in the
methyl acetate:
CH;COH + HSOCH3
CH;Č18OCH3 + H,O
(a) Do the C-OH bond of the acid and the O-H bond
of the alcohol break in the reaction, or do the O-H bond
of the acid and the C-OH bond of the alcohol break?
(b) Imagine a similar experiment using the radioisotope H,
which is called tritium and is usually denoted T. Would the
reaction between CH;COOH and TOCH; provide the same
information about which bond is broken as does the above
experiment with Hl$OCH;?
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