Dolbier HW Solutions 374

Dolbier HW Solutions 374 - 468 ALDEHYDES AND KETONES:...

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B-13. Which sequence represents the best synthesis of hexanal? CH 3 CH 2 CH 2 CH 2 CH 2 CH ? O Hexanal ( a )1 .C H 3 CH 2 CH 2 CH 2 Br 1 NaC > CH ( c . 2. H 2 O, H 2 SO 4 , HgSO 4 2. CH 3 MgBr, diethyl ether 3. H 3 O 1 4. PCC, CH 2 Cl 2 ( b . ( d . CH 3 CH 2 CH 2 CH 2 MgBr 1 H 2 C CH 2 O CH 3 CH 2 CH 2 CH 2 CCH 3 O CH 3 CH 2 CH 2 CH CH 3 COOH CH 2 1 O 468 ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP 2. 2. H 3 O 1 3. LiAlH 4 3. PCC, CH 2 Cl 2 4. H 2 O 5. PCC, CH 2 Cl 2 B-14. The amino ketone shown undergoes a spontaneous cyclization on standing. What is the
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