TOPIC: 18. Aldehydes / Ketones SUBTOPIC: 181. Synthesis 1. Give the major product(s) of the following reaction. CH2OH N+ H ClCrO3 ________________________________________________________________________ ________________________________________________________________________ 2. Give the major product(s) of the following reaction. O NaCN CH3CH2OH H ________________________________________________________________________ ________________________________________________________________________ 3. Show how DIBAH, HAl(i-Bu)2, is used in a reaction by writing an equation. ________________________________________________________________________ ________________________________________________________________________ 4. Show how you would accomplish the following synthetic transformation. Give all reagents and isolated products. H O ________________________________________________________________________ ________________________________________________________________________ 5. Show how you would accomplish the following synthetic transformation. Give all reagents and isolated products. Br O O O H H ________________________________________________________________________ ________________________________________________________________________ 6. Show how you would accomplish the following synthetic transformation. Give all reagents and isolated products. Use benzaldehyde as the only carbon source. O O H ________________________________________________________________________ ________________________________________________________________________ 7. Show how you would accomplish the following synthetic transformation. Give all reagents and isolated products. NCH3 O H ________________________________________________________________________ ________________________________________________________________________ 8. Show how you would accomplish the following synthetic transformation. Give all reagents and isolated products. O O O OEt ________________________________________________________________________ ________________________________________________________________________ 9. Show how you would accomplish the following synthetic transformation. Give all reagents and isolated products. O Br NH2 ________________________________________________________________________ ________________________________________________________________________ 10. Show how you would accomplish the following synthetic transformation. Give all reagents and isolated products. H O _______________________________________________________________________ _______________________________________________________________________ 11. Give the product(s) of the following reaction showing stereochemistry in 3-D and all stereoisomers. OCH3 O HAl -78o C ________________________________________________________________________ ________________________________________________________________________ 12. Write the reagents over the arrow. Number the reagents if they cannot be mixed. CH3 CH3 O ________________________________________________________________________ ________________________________________________________________________ 13. Write the reagents over the arrow. Number the reagents if they cannot be mixed. O ________________________________________________________________________ ________________________________________________________________________ 14. Give the product of the following reaction. O Li Cu Cl ________________________________________________________________________ ________________________________________________________________________ 15. Give the product of the following reaction. OH CrO3 H2SO4 ________________________________________________________________________ ________________________________________________________________________ 16. Write the reagents over the arrow. Number them if they cannot be mixed. H O ________________________________________________________________________ ________________________________________________________________________ 17. Write the reagents over the arrow. Number them if they cannot be mixed. Br Br O ________________________________________________________________________ ________________________________________________________________________ 18. Show how you would accomplish the following synthetic transformation. Give all reagents and isolated products. O H ________________________________________________________________________ ________________________________________________________________________