ALDEHYDES AND KETONES

1. Give an IUPAC name of each of the following compounds:

a) b) c) d) e)

2. Write the structures:

a) 4-methyl-2-pentanone c) dibenzyl ketone e) benzophenone

b) benzyl ethyl ketone d) acetophenone f) acetone

3. Predict the product of reaction of butanal with:

1. LiAlH₄ g) aniline

2. NaBH₄ h) dimethylamine / H⁺

3. H₂/Pt i) hydroxylamine

4. 1) CH₃MgI 2) H₃O⁺ j) Ag₂O

e) k) H₂CrO₄

l) hydrazine 1 mol and 0.5 mol

f) methanol / HCl _(g) m) sodium cyanide

4. Repeat the preceding problem for cyclohexanone from a) to m).

5. What is the principal product in each reaction?

a) b)

c) d)

e)

6. Using ethanol as the source of all the carbon atoms, describe efficient syntheses of each of the following, using any necessary organic and inorganic reagents.

1. 
   d) 3-butyn-1-al

2. 
   e) acetaldehyde diethyl acetal

3. 1-butanol f) 3-butyn-2-ol

7. The following five-step synthesis has been reported in the chemical literature. Suggest reagents appropriate for each step.

8. Synthesis of each of the following compounds have been reported in the chemical literature. Using the indicated starting material and any necessary organic or inorganic reagents, describe short sequences of reactions that would be appropriate for each transformation.

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