1. Organic Chemistry, 6th edition Paula Yurkanis Bruice
Chapter 18
Carbonyl Compounds II
Reactions of Aldehydes and Ketones
More Reactions of Carboxylic Acid Derivatives
Reactions of α,β-Unsaturated Carbonyl Compounds
Brian L. Groh
Minnesota State University, Mankato
Mankato, MN
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

2. Which is the systematic name for the following compound?
18.1
Which is the systematic name for the following compound?
3-methyl-4-oxopentanal
3-methyl-2-oxopentanal
3-methyl-2-oxo-5-pentanal
3-methyl-5-oxo-2-pentanone
3-methylpentan-5-one-1-al
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

3. Which is the systematic name for the following compound?
18.1
Which is the systematic name for the following compound?
3-methyl-4-oxopentanal
3-methyl-2-oxopentanal
3-methyl-2-oxo-5-pentanal
3-methyl-5-oxo-2-pentanone
3-methylpentan-5-one-1-al
The aldehyde group has higher priority than the keto group and is assigned the 1 position.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

4. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
18.2
Which is the correct order of decreasing reactivity toward nucleophilic attack?
Acyl halide
Aldehyde
Carboxylate ion
Carboxylic acid
Ketone
1 > 2 > 3 > 4 > 5
1 > 2 > 5 > 4 > 3
1 > 5 > 2 > 4 > 3
2 > 5 > 1 > 3 > 4
5 > 2 > 1 > 3 > 4
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

5. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
18.2
Which is the correct order of decreasing reactivity toward nucleophilic attack?
Acyl halide
Aldehyde
Carboxylate ion
Carboxylic acid
Ketone
1 > 2 > 3 > 4 > 5
1 > 2 > 5 > 4 > 3
1 > 5 > 2 > 4 > 3
2 > 5 > 1 > 3 > 4
5 > 2 > 1 > 3 > 4
Acid halides are the most reactive carboxylic acid derivative. Aldehydes are more reactive than ketones since they are less hindered and have only one donor group attached to the carbonyl.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

6. Which set of reagents would best accomplish the transformation below?
18.8
Which set of reagents would best accomplish the transformation below?
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

7. Which set of reagents would best accomplish the transformation below?
18.8
Which set of reagents would best accomplish the transformation below?
This is an enamine synthesis commonly used in the Stork reaction.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

8. The role of an acid catalyst in the formation of a ketal is to_____.
18.10
The role of an acid catalyst in the formation of a ketal is to_____.
protonate the C=O making it a better electrophile
protonate the C=O making it more reactive toward weak nucleophiles such as alcohols
protonate the tetrahedral hemiketal which facilitates loss of water
force the equilibrium of the reaction to the right
All of the above
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

9. The role of an acid catalyst in the formation of a ketal is to_____.
18.10
The role of an acid catalyst in the formation of a ketal is to_____.
protonate the C=O making it a better electrophile
protonate the C=O making it more reactive toward weak nucleophiles such as alcohols
protonate the tetrahedral hemiketal which facilitates loss of water
force the equilibrium of the reaction to the right
All of the above
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

10. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
18.13
Which of the following alkenes could not be prepared from cyclohexanone using the Witting reaction?
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

11. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
18.13
Which of the following alkenes could not be prepared from cyclohexanone using the Witting reaction?
The Wittig reagent needed for this alkene cannot be prepared from the highly hindered neopentyl halide.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

12. Which compound is the product of the following sequence of reactions?
18.16
Which compound is the product of the following sequence of reactions?
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

13. Which compound is the product of the following sequence of reactions?
18.16
Which compound is the product of the following sequence of reactions?
1,4-addition of the nitrile followed by hydrolysis gives a saturated keto acid. NaBH4 (CeCl3 not necessary) reduces only the ketone.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.