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Midterm Key - UCLA

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Chemistry 144, Fall 2004 Name: KEY<br />

Page 7<br />

6. (20) Propose detailed mechanisms for the following reactions.<br />

Li<br />

OMe<br />

OMe Li NH3<br />

OMe<br />

H<br />

NH2<br />

OMe NH2<br />

OMe<br />

Li<br />

OMe OMe<br />

H 2O<br />

OMe<br />

H +<br />

OMe<br />

Me<br />

O<br />

O<br />

H<br />

H<br />

H 3O +<br />

Net Tautomerization<br />

(1,5 Hydroden shift)<br />

Me<br />

O H<br />

O<br />

H<br />

H<br />

H<br />

O<br />

H<br />

O<br />

O H<br />

H +<br />

O H<br />

H<br />

O<br />

H<br />

O

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