1.

Using curved arrow formalism, draw each step of the chemistry to form an alcohol using organometallic chemistry with chlorobutene, lithium in ether,propanaldehyde (an aldehyde) and the an acid for workup.

• Step 1 forming the organometallic reagent (show product but no arrows)
• Step 2 SN2 chemistry with the carbonyl (show arrows and product)
• Step 3 workup with acid (show arrows and products.

2.

Using curved arrow formalism, draw each step of the chemistry to form an alcohol using organometallic chemistry withiodoethane, magnesium in ether, ethyl methyl ketone and the acid for workup.

• Step 1 forming the organometallic reagent (show product but no arrows)
• Step 2 SN2 chemistry with the carbonyl (show arrows and product)
• Step 3 workup with acid (show arrows and product)

3. Using an example provided as a template in the drawing file, design the synthesis of two primary alcohols. Propose the structures of the starting alkyl halides.

4. Using an example provided as a template in the drawing file, design the two different methods to synthesize the secondary alcohol. Propose the structures of both the starting alkyl halides and the aldehyde.

5. design the three different methods to synthesize the tertiary alcohol. Propose the structures of the starting alkyl halides and the ketones. You can use the same steps to solve form the structures as you did for solving for the primary and secondary alcohol, just with the tertiary alcohol, you need to draw 3 lines.

6. Complete the challenge question to synthesis a unique tertiary alcohol using organometallic chemistry. There is only one way that this alcohol can be made.