SolutionsChp14

SolutionsChp14 - 3 MgBr to the lactone followed by hydrolysis O O CH 3-MgBr O O-MgBr BrMgO O CH 3 MgBr H 3 O HO OH 3 Br Mg ether MgBr O H 3 O OH

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Chapter 14 Solutions for Problem Set 1. (a) Primary alcohols can be prepared from a Grignard reagent and formaldehyde followed by hydrolysis. MgBr + H O H (b) This is a secondary alcohol which can be prepared from a Grignard reagent and an aldehyde. OH MgBr + H O OR O H CH 3 MgBr + (c) Primary alcohols can be obtained from formaldehyde and a Grignard reagent. In this case, we can also prepare the compound by opening of an epoxide ring. MgBr + H O H OR MgBr + O (d) Tertiary alcohol can be prepared in the following ways: (a) Reaction of a Grignard reagent with a ketone (b) Two molecules of a Grignard reagent with an ester, or acid chloride.
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+ O CH 3 MgBr + MgBr 2 CH 3 MgBr + O O OEt O Cl 2. This is an ester functionality, but it’s a cyclic ester or a lactone. The transformation can be achieved by adding 2 molecules of CH
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Unformatted text preview: 3 MgBr to the lactone followed by hydrolysis. O O CH 3-MgBr O O-MgBr BrMgO O CH 3 MgBr H 3 O + HO OH 3. Br + Mg ether MgBr + O H 3 O + OH Alternatively, the secondary alcohol can also be obtained by reaction of an aldehyde with a Grignard reagent. H O + MgBr OR O H + MgBr 4. HC CH NaNH 2 HC CNa O H 3 O + OH 5. Secondary alcohols can be prepared by reaction of a Grignard reagent with an aldehyde, or by reaction of two molecules of Grignard reagent with the ester of formic acid followed by hydrolysis. MgBr + H O OR MgBr + H OEt O 2 6. a. CH 4 + O OH b. Ph OH c. OH d. OH e. Ph Ph Ph OH f. 7. R-MgX + O R OMgBr H 3 O + R OH 8. CH 2 Br 2 K +-OC(CH 3 ) 3 (CH 3 ) 3 COH H Br 9. OH OH 10. a. 4 b. 2 c. 3 d. 2 e....
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This note was uploaded on 01/24/2010 for the course CHEM 234 taught by Professor Miranda during the Spring '07 term at Ill. Chicago.

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SolutionsChp14 - 3 MgBr to the lactone followed by hydrolysis O O CH 3-MgBr O O-MgBr BrMgO O CH 3 MgBr H 3 O HO OH 3 Br Mg ether MgBr O H 3 O OH

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