Some examples from this set of practice questions
1.
What protecting group must be used to synthesize methylene from a carbonyl group?
Answer: Thiol Acetals can be used with Rainey Nickel and H3o+ to turn a carbonyl group (Ketone/aldehydes/esters) into hydrocarbons
2.
What are the limitations of using Grignard\'s reagent in a reaction?
Answer: - No water or acidic protons can be in the substrate (OH-, NH-, SH-, etc.) - No electrophilic/multiple bonds (This causes Grignard\'s to attack both carbonyl carbons) (N2,NO, SO, CN) -Grignard\'s will attack twice if the reaction has acid halides and esters.
3.
What are the limitations of using Gilmann\'s reagent in a reaction?
Answer: - Gilmann\'s doesn\'t react with carbonyl groups -Gilmann will not react with an alkene if there is no carbonyl group attached as well - Gilmann will attack in a 1,4 addition if there is a carbonyl with an alkene -Gilmann attacks in a conjugate addition if the reaction is with the normal organocuperate
4.
What normally attacks at the alpha position?
Answer: - Grignard\'s reagent - Organolithium - LDA and substrate
5.
What normally attacks at the Beta Position?
Answer: - Organocuperates - Thiols - Enolates
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