Hiram College, Chem. 320, Spring 2010
Puzzle 4
2/19/10
1. Predict the products for the following reactions.
Hiram College, Chem. 320, Spring 2010
2. Do you remember these reactions?
Show syntheses of these compounds. You may start with any alcohols containing four or less
carbons, any inorganic reagents, and any solvents you need.
3. Many of the nucleophilic addition reactions to carbonyl carbons are actually equilibrium
processes. The addition of a Grignard, a hydride, or an acetylide is not a equilibrium process.
Why?
Hiram College, Chem. 320, Spring 2010
4. Addition of alcohols to aldehydes and ketones produces acetals and ketals, respectively. One
example of such a reaction is shown below. Propose a reasonable mechanism for the following
transformation.
5. Using the information above as a guide, predict the products of the following reactions.
Hiram College, Chem. 320, Spring 2010
6. Nitriles are good electrophiles, and tend to undergo reactions similar to those of carbonyl
compounds. One nucleophile they react with quite well is a Grignard reagent. After an acidic
work-up, the product of this sequence is a ketone. Propose a reasonable mechanism for the
following transformation.
7. Based on what you reasoned above, predict the products for the following reactions.
CH3CH2CH2
C N:
1) EtMgBr
2) H3O+
1) PhMgBr
2) H3O+
(CH3) 2CHCH2
C N:
CH3
1) MeMgBr
2) H3O+
C N: