Addition of oxygen nucleophiles: ROH add'n w/acid cat.; prep. of stable acetals 18.13) ● ● aldehydes/ketones react w/ROH to form unstable/unisolable hemiacetals aldehydes/ketones react w/2 equiv. of ROH and acid catalyst to afford stable/isolable acetals, with a hemiacetal as a mechanistic intermediate Sample rxn: Propose the mechanism: + 2 CH3 H H* (cat.) X OCH3 + (chap. 17 & 18) Note: acetal carbon has same oxid. state as C=O carbon OCH3 H an acetal (NOT an ether or "diether")

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Addition of oxygen nucleophiles: ROH add'n w/acid cat.; prep. of stable acetals
(18.13)
aldehydes/ketones react w/ROH to form unstable/unisolable hemiacetals
aldehydes/ketones react w/2 equiv. of ROH and acid catalyst to afford stable/isolable acetals,
with a hemiacetal as a mechanistic intermediate
Sample rxn:
Propose the mechanism:
CH3
2:0
H
H* (cat.)
OCH 3
OCH 3
an acetal (NOT an ether or "diether")
+
(chap. 17 & 18)
H
Note:
acetal carbon has
same oxid. state
as C=O carbon
11
Transcribed Image Text:Addition of oxygen nucleophiles: ROH add'n w/acid cat.; prep. of stable acetals (18.13) aldehydes/ketones react w/ROH to form unstable/unisolable hemiacetals aldehydes/ketones react w/2 equiv. of ROH and acid catalyst to afford stable/isolable acetals, with a hemiacetal as a mechanistic intermediate Sample rxn: Propose the mechanism: CH3 2:0 H H* (cat.) OCH 3 OCH 3 an acetal (NOT an ether or "diether") + (chap. 17 & 18) H Note: acetal carbon has same oxid. state as C=O carbon 11
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