Name: Score: /102 = %

ASSIGNMENT NO. 6
CARBOXYLIC ACIDS AND DERIVATIVES

Note: submit only the accompanying answer sheet.

I. Provide the answer on the space provided in the answer sheet. (2 pts each number)

1. Acidic hydrolysis of cyanohydrins converts them to:

or _ .

2. Reduction of an ester or nitrile to an aldehyde can be accomplished using and

temperature.

3. Acyl compounds tend to react by acyl substitution mechanisms because they all have a good

or reasonably good attached to the carbonyl carbon.

4. An acid catalyzed reaction between a carboxylic acid and an alcohol is called a

_ .

5. Base-promoted hydrolysis of esters is sometimes called .

6. The only carboxylic acid derivative with two carbonyl groups is the .

7. The presence of electron-withdrawing substituents close to the carboxylic acid functional group

will the acidity of the molecule.

II. Descriptive Multiple Choice. Write the letter only. (2 pts each)

1. Which compound would be the strongest acid?

2. Which compound would be most reactive toward nucleophilic acyl substitution?

3. The relative reactivity of acyl compounds toward nucleophilic substitution is:

A) Amide > ester > acid anhydride > acyl chloride

B) Acyl chloride > ester > acid anhydride > amide
C) Ester > acyl chloride > acid anhydride > amide
D) Acyl chloride > acid anhydride > ester > amide
E) Acid anhydride > acyl chloride > ester > amide

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4. Which of the following will not undergo hydrolysis to produce carboxylic acid, whether acid
or base is present?

5. An acid chloride is prepared from the related carboxylic acid by reaction with which of these?

A) HCl B) Cl C) SOCl D) HOCl E) AlCl

2 2 3

6. Which of the following reagents will convert insoluble carboxylic acids into soluble one?

A) sodium hydroxide B) sodium bicarbonate C) sodium chloride

D) all of these E) none of these

7. Amides can be synthesized from carboxylic acid with the use of :

A) dicyclohexyl-carbodiimide D) N.N-dimethyl carboxamide

B) pyridinium chlorochromate E) none of these
C) pyridine

8. Heating of the acid, CH3CH2COCH2COOH at 100-150 0C will produce and release

the gas .

A) CH3CH3; CO2 D) CH3CH2COCH3; O2

B) CH3CH2COCH3; CO2 E) None of these
C) CH3CH2COOH; CO2

9. Which of the following methods can be used to synthesize carboxylic acids?

A) Carbonation of Grignard reagents
B) Oxidation of the benzene ring
C) Oxidation of alkenes
D) All of these
E) None of these

10. Which of the following is an anhydride?

A) B) C) D)

11. Which of the following methods would be suitable for making acid chloride C?

A) hexanal + Cl2/heat B) 1-chlorohexane + CrO3

C) hexanoic acid and SOCl2 D) hexanoic acid anhydride + Cl–

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12. What is the acid anhydride that is hydrolyzed?

A) B) C) D)

13. Acetic anhydride is less reactive toward attack by a nucleophile than

A) acetic acid. B) ethyl acetate. C) acetyl chloride. D) acetonitrile.

14. Rank the following acid derivatives in order from most reactive to least reactive.

A) 1 > 4 > 2 > 3 B) 3 > 1 > 2 > 4 C) 2 > 3 > 1 > 4 D) 4 > 2 > 3 > 1

15. Which of the following is not an acid derivative?

A) B) C) D)

16. Predict the product of the following reaction.

A) B) C) D)

17.What is the product formed when benzonitrile is treated with phenylmagnesium bromide
followed by acid hydrolysis?
A) benzophenone B) benzyl alcohol C) benzaldehyde D) triphenylmethyl amine

18. Which of the following products are obtained upon heating ethyl benzoate with dilute
sodium hydroxide?
A) sodium benzoate and ethanol B) benzoic acid and sodium ethoxide
C) benzoic acid and ethanol D) sodium benzoate and sodium ethoxide

19. What is the product of the following reactions? (Write out the 5 steps in your scratch paper.)

A) B) C) D)

20. Which of the following carboxylic acid derivatives is most difficult to hydrolyze?

A) B) C) D)

21. Which compound does not react with ammonia to form propanamide under mild conditions?
A) propanoic acid B) propanoyl chloride C) ethyl propanoate D) propanoic anhydride

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22.Which of the following reagents would be best for reducing an ester to an aldehyde?
A) LiAlH4 in ether B) B2H6 in ether C) NaBH4 in aqueous ethanol
D) diisobutylaluminum hydride (DIBAL-H) in toluene at -78 ºC

23. Which of the following reagents are suitable for reducing an amide to an aldehyde?

A) LiAlH4 in ether B) diisobutylaluminum hydride (DIBALH) in toluene

at -78 ºC
C)LiAlH(t-C4H9O)3 in ether at -
D)NaBH4 in aqueous ethanol
78 ºC
24. Which of the following reactions is most likely to produce ethyl propanoate?
A) sodium ethoxide + propanoic acid B) propanol + acetyl chloride
C) sodium propanoate + acetic anhydride D) potassium propanoate + ethyl iodide

25. Which of the following will be the favored product from the reaction shown below?

26.Which of the following reagents would be best for converting phenylacetamide

(C6H5CH2CONH2) to benzylamine (C6H5CH2NH2)?
A) LiAlH4 in ether. B) i) P2O5 & heat; ii) LiAlH4 in ether.
C) H2 & Pt catalyst. D) aqueous NaOBr.

27. Which of the following reagents and conditions would be best for the preparation
of cyclohexylamine?

A) cyclohexanone + NH3 + NaBH3CN. B) cyclohexylbromide + 2 NH3.

C) cyclohexene + NH3. D) none

28. Which of the following compounds is not a derivative of the carboxylic acids?
a) maleic anhydride b) propanoyl chloride c) N-ethylethanamide

d) acetonitrile e) none of these

29. Which of the following is the poorest starting material in the synthesis of esters?

a) acyl chloride b) acid anhydride c) amides d) none of these e) all of these

30. Which of the following reagents will convert insoluble carboxylic acids into soluble one?
a) sodium hydroxide b) sodium bicarbonate c) sodium chloride d) all of these

31.Cyclic anhydrides can be prepared by heating dicarboxylic acids when anhydride formation
leads to membered rings. a) four b) six c) seven d) eight

32. Saponification is:

a) Fischer Esterification b) base-promoted hydrolysis of esters
c) acid hydrolysis of esters d) all of the above

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III. Predict the major organic product of the following: (2 pts. Each)

1. _

2.

3.

4.

12. _