Dolbier HW Solutions 302

Dolbier HW Solutions 302 - 6 H 5 CH 2 OH to benzaldehyde b...

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A-3. Write the structure of the major organic product formed in the reaction of 2-propanol with each of the following reagents: ( a ) Sodium amide (NaNH 2 ) ( b ) Potassium dichromate (K 2 Cr 2 O 7 ) in aqueous sulfuric acid, heat ( c ) PDC in dichloromethane ( d ) Acetic acid in the presence of dissolved hydrogen chloride ( e ) in the presence of pyridine ( f ) in the presence of pyridine ( g ) in the presence of pyridine A-4. Outline two synthetic schemes for the preparation of 3-methyl-1-butanol using different Grignard reagents. A-5. Give the structure of the reactant, reagent, or product omitted from each of the following. Show stereochemistry where important. ( a ) ( b ) ( c ) A-6. Give the reagents necessary to carry out each of the following transformations: ( a ) Conversion of benzyl alcohol (C
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Unformatted text preview: 6 H 5 CH 2 OH) to benzaldehyde ( b ) Conversion of benzyl alcohol to benzoic acid (C 6 H 5 CO 2 H) ( c ) Conversion of to ( d ) Conversion of cyclohexene to cis-1,2-cyclohexanediol A-7. Provide structures for compounds A to C in the following reaction scheme: K 2 Cr 2 O 7 H 1 , H 2 O CH 3 OH, H 1 1. LiAlH 4 2. H 2 O H 1 , heat A(C 5 H 12 O 2 ) B(C 5 H 8 O 3 ) C(C 6 H 10 O 3 ) A 1 CH 3 OH H 3 C O CHCH 2 CH 2 CH 2 OH H 2 C CHCH 2 CH 2 CO 2 H H 2 C (C 6 H 5 CH O) OsO 4 , (CH 3 ) 3 COOH (CH 3 ) 3 COH, HO 2 ? 2,3-butanediol (chiral diastereomer) H 1 heat ? (a diol) CH 3 O OH OH H CH 3 HIO 4 ? CH 3 COCCH 3 O O CCl CH 3 CH 2 O SO 2 Cl H 3 C (CH 3 COH) O 396 ALCOHOLS, DIOLS, AND THIOLS...
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This note was uploaded on 09/28/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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