CHEM 2425. Review for Test 3 (chapter 19, 20, 21)

pg. 1 CHEM 2425. Review for Test 3 (chapter 19, 20, 21)

CHEM 2425. Review for Test 3 (chapter 19, 20, 21)

True/False Indicate whether the statement is true or false.

____ 1. An 1H NMR is run on a sample. This spectrum is shown below.

Based on this data the sample is probably an aldehyde.

____ 2. Of the types of reactions that characterize carbonyl groups, the following reaction would be classified as

an α substitution.

____ 3. The correct name for the following compound is 3-oxoheptanal.

____ 4. The correct name for the following compound is trans-1,3-cyclopentanedicarbaldehyde.

____ 5. Consider the following reaction.

The mechanism for this reaction is shown below.



The product of this reaction is a vicinal diol.

____ 7. Many nucleophilic addition reactions of aldehydes and ketones are catalyzed by acid or base. Bases

catalyze hydration by converting the water to hydroxide ion, a much better nucleophile

____ 8. The product of the following reaction would be an imine.

____ 9. The following compound would be classified as a hemiacetal..

____ 10. 3-hydroxybutanal can exist in equilibrium as a cyclic hemiacetal.

____ 11. The following compound can be produced by the reaction of cyclohexanecarbaldehyde and

.

____ 12. The structure of cis-1,3-cyclopentanedicarboxylic acid is shown below.

____ 13. Consider the data in the Table below to answer the following question:

Acidities of Substituted Benzoic and Acetic Acids

pKas at 25°C


Y−C6H4COOH Y Y−CH2COOH meta para H 4.75 4.19 4.19

CN 2.47 3.64 3.55 OCH3 3.57 4.09 4.46

The structure of the strongest acid in the table above is NC−CH2−COOH.

____ 14. Consider the data in the Table below to answer the following question:

Acidities of Substituted Benzoic and Acetic Acids

pKas at 25°C Y−C6H4COOH

Y Y−CH2COOH meta para H 4.75 4.19 4.19

CN 2.47 3.64 3.55 OCH3 3.57 4.09 4.46

The structure of the acid with the strongest conjugate base in the table above is CH3COOH.

____ 15. Benzoic acid can be produced by the treatment of bromobenzene with 1. Mg, ether, and 2.) CO2 followed

by acidification.


The major organic product obtained is


The major organic product obtained is

____ 18. Consider the following 1H NMR to answer the following question.


Spectrum obtained from: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology, 11-07-08) This compound is known to contain both a −C=O group and an −OH group. Based on this spectrum, this compound would be classified as aliphatic carboxylic acid.

____ 19. Based on the following IR spectrum, this compound would be classified as aromatic carboxylic acid.

Spectrum obtained from: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology, 11-07-08)


The expected product is


____ 21. Malonic acid is an example of a β-ketoacid.

____ 22. The following compound should be named as cyanopropane.

____ 23. The product of the following reaction would be classified as a carboxylic acid.

____ 24. Both amides and nitriles are acyl derivatives of carboxylic acids.

____ 25. The correct name of the following structure is phenyl benzoate.


The correct reactant to place in the box is PCl3.


The reactant is a lactam.

____ 28. The correct name for the following compound is propyl cyclohexanoate.


____ 29. Consider the isotopically tagged substance below.

Saponification of this substance will produce the following products.


The structure of the tetrahedral intermediate is

____ 31. Of the following substances, the first and last substance shown are not derivatives of carboxylic acids.

____ 32. It is possible to directly convert an acid anhydride to an acid chloride.

Completion Complete each statement.

Consider the reaction below to answer the following question(s). Use letters where appropriate to answer the questions.


1. The nucleophile in this reaction is _____.

2. The catalyst in this reaction is _____.

3. The product of this reaction is called a(n)___________.

4. The first step in the reaction mechanism is the protonation of the ________group.

Consider each of the spectrum and answer the following questions using the appropriate number.

5. The peak labeled _____ would allow the distinction of an aldehyde from a ketone based on this spectrum.

6. The peak labeled _____ would allow the distinction of an aldehyde from a ketone based on this spectrum.

Answer each of the following questions with the appropriate number.

7. The number of α-hydrogens in the following compound is _____.


8. The number of hydrogens in the following compound that will be exchanged for deuterium upon reaction

with D2O and an acid catalyst is _____.

9. In the following compound, the most acidic hydrogen atom(s) are numbered as _____.

10. Of the compounds shown below, the one numbered _____ has the highest boiling point.

11. Of the compounds shown below, the one numbered _____ is an imine.

12. Of the compounds shown below, the one numbered _____ is an enamine.

13. Of the compounds shown below, the one numbered _____ is an enamine.


14. Provide the correct name for the following compound which can be used to produce aspirin.

15. When CO2 is bubbled through an ether solution of benzylmagnesium bromide, and the resulting mixture is

acidified, ____________ _____ is produced.

16. The strongest acid of the following is indicated by the Roman numeral ______.

17. The strongest acid of the following is indicated by the Roman numeral ______.

Based on the informaton presented below, answer the following questions. An ether solution contains the following components. 2,3,4,5-tetramethylbenzene benzyl alcohol 2-hydroxybenzoic acid This solution is extracted with a 1.0 M solution of NaOH, that is immiscible with ether.

18. The 2,3,4,5-tetramethylbenzene will be recovered from the _______ layer.

19. The benzyl alcohol will be recovered from the _______ layer.

20. The 2-hydroxybenzoic acid will be recovered from the _______ layer.

21. In order to recover the 2-hydroxybenzoic acid, a strong ______ must be added to the appropriate layer.

22. Ethyl propanoate (CH3CH2COOCH2CH3) can be prepared by the reaction of ethanol with ____________

acid.

23. Pentanoic acid can be converted to its methyl ester in very high yield by reaction with

___________________.


24. Consider the following spectrum of a carboxylic acid derivative.

This spectrum indicates the presence of a ___________group.

Consider the following general structures.

Use the Roman numeral of the substance to answer the following questions.

25. The substance that is the most reactive toward nucleophilic acyl substitution is _____.

26. The substance that is the least reactive toward nucleophilic acyl substitution is _____.

27. The substance that is classified as an anhydride is _____.

28. Consider the following 1H NMR spectrum.

The line indicated with the number _____ would indicate the presence of a C=O group.

29. Consider the structure given below.

The systematic name for this compound is:

30. Consider the following reaction.


The name of the product of this reaction is_______________________.

31. Consider the following reaction

The name of the reactant that should be placed in the box is _____________.

32. The structure that best describes the double bond character of the amide bond in acetamide is

shown by the Roman numeral _______.

Consider the following compounds.

Use the numbers shown to answer the following questions. If none of the structures is applicable enter the word none.

33. A lactone is represented by the structure numbered ____.

34. An anhydride is represented by the structure numbered ____.

35. An imide is represented by the structure numbered ____.

Problem

1. What is the IUPAC name of the following compound?



3. What is the major organic product obtained from the following reaction?















16. What is the major organic product obtained from the following sequence of reactions?

























38. What two organic compounds are obtained from the following reaction?


















CHEM 2425. Review for Test 3 (chapter 19, 20, 21) Answer Section

TRUE/FALSE

1. ANS: T PTS: 1

2. ANS: T PTS: 1

3. ANS: F PTS: 1

4. ANS: F PTS: 1

5. ANS: T PTS: 1

6. ANS: F PTS: 1

7. ANS: T PTS: 1

8. ANS: F PTS: 1

9. ANS: T PTS: 1

10. ANS: F PTS: 1

11. ANS: F PTS: 1

12. ANS: T PTS: 1

13. ANS: T PTS: 1

14. ANS: T PTS: 1

15. ANS: T PTS: 1

16. ANS: F PTS: 1

17. ANS: F PTS: 1

18. ANS: F PTS: 1

19. ANS: T PTS: 1

20. ANS: T PTS: 1

21. ANS: F PTS: 1

22. ANS: F PTS: 1

23. ANS: T PTS: 1

24. ANS: F PTS: 1

25. ANS: T PTS: 1

26. ANS: F PTS: 1

27. ANS: F PTS: 1

28. ANS: F PTS: 1

29. ANS: F PTS: 1

30. ANS: F PTS: 1

31. ANS: T PTS: 1

32. ANS: F PTS: 1

COMPLETION

1. ANS: A

PTS: 1

2. ANS: C

PTS: 1


3. ANS: acetal

PTS: 1

4. ANS: carbonyl ketone

PTS: 1

5. ANS: 2

PTS: 1

6. ANS: 1

PTS: 1

7. ANS: 4 four

PTS: 1

8. ANS: 4 four

PTS: 1

9. ANS: 2 two

PTS: 1

10. ANS: 2 two

PTS: 1

11. ANS: 2 two

PTS: 1

12. ANS: 3 three

PTS: 1

13. ANS: 3 three

PTS: 1

14. ANS:


o-hydroxybenzoic acid o-hydroxybenzoic acid 2-hydroxybenzoic acid

PTS: 1

15. ANS: phenylacetic acid phenylethanoic acid

PTS: 1

16. ANS: IV

PTS: 1

17. ANS: III

PTS: 1

18. ANS: ether

PTS: 1

19. ANS: ether

PTS: 1

20. ANS: base basic NaOH aqueous

PTS: 1

21. ANS: acid

PTS: 1

22. ANS: propanoic propionic

PTS: 1

23. ANS: diazomethane

PTS: 1

24. ANS: nitrile

PTS: 1

25. ANS: IV

PTS: 1

26. ANS: II

PTS: 1

27. ANS: 1


PTS: 1

28. ANS: 5

PTS: 1

29. ANS: Ethyl p-aminobenzoate ethyl p-aminobenzoate Ethyl 4-aminobenzoate ethyl 4-aminobenzoate

PTS: 1

30. ANS: hexane-2,6-diol

PTS: 1

31. ANS: methanol methyl alcohol

PTS: 1

32. ANS: II

PTS: 1

33. ANS: 1 one

PTS: 1

34. ANS: 2 two

PTS: 1

35. ANS: 3 three

PTS: 1

PROBLEM

1. ANS:

(S)-2-chloropentanal

PTS: 1

2. ANS: (S)-3-methyl-2-pentanone

PTS: 1


3. ANS:

PTS: 1

4. ANS:

PTS: 1

5. ANS:

PTS: 1

6. ANS:

PTS: 1

7. ANS:

PTS: 1

8. ANS:

PTS: 1

9. ANS:

PTS: 1

10. ANS:


PTS: 1

11. ANS:

PTS: 1

12. ANS:

PTS: 1

13. ANS:

PTS: 1

14. ANS:

PTS: 1

15. ANS:

PTS: 1

16. ANS:


PTS: 1

17. ANS:

PTS: 1

18. ANS:

PTS: 1

19. ANS:

PTS: 1

20. ANS: (Z)-2-butenoic acid

PTS: 1

21. ANS: (E)-3-pentenoic acid

PTS: 1

22. ANS:

PTS: 1

23. ANS:

PTS: 1

24. ANS:


PTS: 1

25. ANS:

PTS: 1

26. ANS:

PTS: 1

27. ANS:

PTS: 1

28. ANS:

PTS: 1

29. ANS:


PTS: 1

30. ANS:

PTS: 1

31. ANS:

PTS: 1

32. ANS: (Z)-ethyl 2-methyl-2-butenoate

PTS: 1

33. ANS: (Z)-N,N-dimethyl-3-pentenamide

PTS: 1

34. ANS:

PTS: 1

35. ANS:

PTS: 1

36. ANS:

PTS: 1

37. ANS:


PTS: 1

38. ANS:

PTS: 1

39. ANS:

PTS: 1

40. ANS:

PTS: 1

41. ANS:

PTS: 1

42. ANS:

PTS: 1

43. ANS:


PTS: 1

44. ANS:

PTS: 1

45. ANS:

PTS: 1

46. ANS:

PTS: 1

47. ANS:

PTS: 1

48. ANS:

PTS: 1

49. ANS:


PTS: 1

50. ANS:

PTS: 1

51. ANS:

PTS: 1

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CHEM 2425. Review for Test 3 (chapter 19, 20, 21)