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_organometallics wkst

_organometallics wkst - Chapter 15 Organometallics 1...

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Chapter 15: Organometallics 1. Grignard reactions can be performed in all of the following solvents except: a. THF b. ether c. chloroform 2. Which halogens are best for the Grignard reagent RMgX: a. I b. Br c. Cl d. F 3. Organometallic reactions must be performed: a. without oxygen b. without water c. under Ar or N 2 4. Vinyl halides react best with: a. Gilman reagents (R 2 CuLi) b. Grignard reagents (RMgBr) c. Simmons-Smith reagents (CH 2 I 2 , ZnCu) 5. “Killing” a reaction with hydrogen source: Alcohol, 1 o /2 o amine, terminal alkyne ( RC CH ), water, phenol, thiol, carboxylic acid a. Li + H 2 O b. MgBr + CH 3 OH c. NH 3 + 3 Li d. MgI C HC H C M g B r + + CH 3 CH 3 6. Making a Grignard reagent: Br MgBr 7. Grignard reaction: attacks least hindered side of epoxide. Indicate single or racemic product. a. MgBr O H CH 3 H H OH CH 3 H H H + 1. ether 2. HCl (aq) (S)
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b. Find two ways to synthesize the product with an epoxide and a Grignard reagent. OH 8. Gilman’s reagent. Indicate single or racemic product.
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