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Chapter 21 Skills

1.  Provide IUPAC names for carboxylic acids and their derivatives.

2.  Recall the spectroscopic properties of carboxylic acids and their

derivatives.3.  Predict which part of a carboxylic acid (or a derivative) will act as an

acid/electrophile. Explain.

4.  Predict which part of a carboxylic acid (or a derivative) will act as a

base/nucleophile. Explain.

5.  Recognize the ability of carboxylic acids to act as Brønsted-Lowry

acids. Recall the use of Ka or pKa to describe acid strength.

6.  Be able to predict (qualitatively) the strength of various carboxylic

acids. Explain.

7.  Compare the similarities and differences between carboxylic acidsand carboxylate ions. Predict which form predominates at a given pH.

How does that affect solubility?

8.  Recall the oxidation reactions that produce carboxylic acids.

9.  Predict the product when a Grignard reagent is added to CO2 

(followed by H3O+). Provide a mechanism.

10. Predict the product when a nitrile reacts with H3O+ or OH-/H2O.

Provide a mechanism.

11. Predict the product when a carboxylic acid reacts with OH- followed

by R-X. Provide a mechanism. Describe the limitations of this reaction.12. Predict the product when a carboxylic acid reacts with RLi (followed

by H3O+). Provide a mechanism.

13. Predict the product when a carboxylic acid reacts with LiAlH4 

(followed by H3O+). Provide a mechanism.

14. Predict the product when a carboxylic acid reacts with BH3-THF.

15. Predict the product when a carboxylic acid reacts with ROH in the

presence of H+. Provide a mechanism. Understand the application of Le

Chatelier’s principle to produce the desired result. 

16. Predict the product when a carboxylic acid reacts with ROH in thepresence of OR-. Provide a mechanism.

17. Predict the product when a carboxylic acid reacts with either SOCl2 

or (COCl)2. Provide a mechanism.

18. Be able to predict (qualitatively) the reactivity/stability of various

carboxylic acid derivatives. Provide an explanation. Describe the

evidence that supports the explanation.

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19. Predict the product when a carboxylic acid derivative is reacted with

a nucleophile. Recognize what conditions are required (acidic, basic or

neutral). Provide a mechanism, including appropriate intermediates for

the conditions. Recognize when no reaction will occur.

20. Describe why “bad” leaving groups are permitted when carboxylic acidderivatives react with strong nucleophiles.

21. Describe why pyridine is frequently added when acid chlorides react

with neutral nucleophiles.

22. Recognize what conditions are necessary to hydrolyze each carboxylic

acid derivative. Predict when the hydrolysis of a carboxylic acid

derivative is in equilibrium versus when it has a driving force.

23. Recognize which reactions to convert between carboxylic acid

derivatives are favorable. Provide reagents.

24. Predict the product when a carboxylic acid derivative reacts withLiAlH4 (followed by H3O

+). Provide a mechanism (acid chlorides and

esters only).

25. Predict the product when a carboxylic acid derivative reacts with RLi

or RMgBr (followed by H3O+). Provide a mechanism.

26. Predict the product when an acid chloride reacts with R2CuLi (followed

by H3O+). Provide a mechanism.

27. Predict the product when an acid chloride reacts with LiAlH(OtBu)3 

(followed by H3O+). Provide a mechanism.

28. Predict the product when an ester reacts with DIBAH (followed by

H3O+).

29. Provide a mechanism to an unknown reaction that is consistent with

the reaction conditions.

30. For the reactions listed above, be able to determine the reagents if

given the starting material and the product. Also be able to determine

the starting material if given the reagents and the product.

31. Be able to propose short syntheses using a combination of the

reactions listed above.