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CHEM 2425. Chapter 18. Ethers and Epoxides, Exams of Organic Chemistry

Indiana State University (ISU)Organic Chemistry

Choose the best reagent for carrying out the following reactions from the list below. Place the letter of the reagent(s) in the box over the reaction arrow.

Typology: Exams

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CHEM 2425. Chapter 18. Ethers and Epoxides; Thiols and Sulfides (homework) W
CHEM 2425. Chapter 18. Ethers and Epoxides; Thiols and Sulfides (homework) W
Short Answer
Drawing Instructions: Draw structures corresponding to each of the given names.
1. Draw: tetrahydrofuran
2. Draw: 12-crown-4
3. Draw: 1-isopropoxycyclopentene
4. Draw: allyl benzyl ether
5. Draw: diethyl ether
6. Draw: 3-methyl-1-butanethiol
7. Draw: cyclopropyl ethyl sulfide
IUPAC Naming Instructions: Provide proper IUPAC names.
8. Name:
9. Name:
10. Name:
Exhibit 18-1
Consider the reaction below to answer the following question(s).
pf3
pf4
pf5
pf8
pf9
pfa
pfd
pfe
pff
pf12
pf13
pf14
pf15

Partial preview of the text

Download CHEM 2425. Chapter 18. Ethers and Epoxides and more Exams Organic Chemistry in PDF only on Docsity!

CHEM 2425. Chapter 18. Ethers and Epoxides; Thiols and Sulfides (homework) W

Short Answer

Drawing Instructions : Draw structures corresponding to each of the given names.

  1. Draw: tetrahydrofuran
  2. Draw: 12-crown-
  3. Draw: 1-isopropoxycyclopentene
  4. Draw: allyl benzyl ether
  5. Draw: diethyl ether
  6. Draw: 3-methyl-1-butanethiol
  7. Draw: cyclopropyl ethyl sulfide

IUPAC Naming Instructions : Provide proper IUPAC names.

  1. Name:
  2. Name:
  3. Name:

Exhibit 18- Consider the reaction below to answer the following question(s).

  1. Refer to Exhibit 18-1. Write the complete stepwise mechanism for the reaction. Show all intermediate structures and all electron flow with arrows.
  2. Refer to Exhibit 18-1. Mechanistically, the Williamson ether synthesis outlined above is:

a. an E1 process b. an SN 1 process c. an E2 process d. an SN 2 process

  1. Refer to Exhibit 18-1. Alternatively, cyclopentyl methyl ether may be synthesized from cyclopentene. Outline a synthesis of cyclopentyl methyl ether from cyclopentene.
  2. Diphenyl ether is inert to cleavage by HI or HBr. Explain.
  3. Write the complete stepwise mechanism for the reaction below. Show all electron flow with arrows and draw all intermediate structures.

Exhibit 18- Consider the data below to answer the following question(s).

Acetals are a special class of ethers which have two ether linkages at a single carbon. Tetrahydropyranyl ethers are acetals that are easily cleaved with mild aqueous acids at room temperature to yield alcohols.

  1. Refer to Exhibit 18-2. Draw arrows showing the electron flow for this reaction on the structures provided below.
  1. Refer to Exhibit 18-3. The synthesis of epoxides by base treatment of halohydrins is an example of an intramolecular:

a. SN 1 reaction b. hydrolysis reaction c. dehydration reaction d. Williamson ether synthesis

Exhibit 18- Propose structure(s) for the starting material(s), reagent(s), or major organic product(s) of the following reactions or sequences of reactions. Show all relevant stereochemistry.

A. NaH, then CH 3 I B. NaOCH 3 , CH 3 OH

C. m - ClC 6 H 4 CO 3 H D. CH 3 MgBr in ether, then H 3 O+

E. warm H 2 SO 4 /H 2 O F. Hg(O 2 CCF 3 ) 2 , CH 3 OH

G. H 2 /Pd H. PCC, CH 2 Cl 2

I. Cl 2 , H 2 O J. LiAlH 4 in ether, then H 3 O+

  1. Complete the synthetic sequence below by drawing the structures of the reaction in the boxes provided.
  2. Show how the ether below could be prepared from toluene and any other necessary reagents. Show all reagents and all intermediate structures.
  3. Propose a synthesis for the following compound using benzene or toluene and any other reagents necessary. Show all major intermediate compounds that would probably be isolated during the course of your synthesis.
  1. Name the compound shown below. Atoms other than carbon and hydrogen are labeled.
  2. Name the following compound. Atoms other than carbon and hydrogen are labeled.
  3. Predict the product of the following reaction.
  4. Draw the structure of the ether that could be used to produce the following compound

Multiple Choice Identify the choice that best completes the statement or answers the question.

a. 6 b. 4 c. 9 d. 5 e. 7 f. 8

____ 47. Consider the following species. Atoms other than carbon and hydrogen are labeled.

Which of the following would be produced upon treatment with I 2 ,? a.

b.

c.

d.

____ 48. What is the product formed upon treatment of the following substance with hydrogen peroxide at room temperature, followed by treatment with a peroxyacid? Atoms other than carbon and hydrogen are labeled.

a.

b.

c.

d.

____ 49. Which of the following will undergo rearrangement upon heating? a. 2-pentenyl phenyl ether

CHEM 2425. Chapter 18. Ethers and Epoxides; Thiols and Sulfides (homework) W

Answer Section

SHORT ANSWER

1. ANS:

PTS: 1

2. ANS:

PTS: 1

3. ANS:

PTS: 1

4. ANS:

PTS: 1

5. ANS:

CH 3 CH 2 OCH 2 CH 3

PTS: 1

6. ANS:

PTS: 1

7. ANS:

PTS: 1

8. ANS:

m -chloroanisole or m -chloromethoxybenzene or ( m -chlorophenyl) methyl ether

PTS: 1

  1. ANS: 1-ethoxy-2,2-dimethylpropane or ethyl neopentyl ether

PTS: 1

  1. ANS: dicyclohexyl sulfide

PTS: 1

  1. ANS:

PTS: 1

12. ANS:

d

PTS: 1

  1. ANS:

PTS: 1

14. ANS:

Acidic ether cleavages are typical nucleophilic substitution reactions that take place by either an SN 1 or SN 2 pathway. Diaryl ethers like diphenyl ether are inert under ordinary acidic conditions because the generation of an aryl cation is an SN 1 process that is energetically unfavorable, and "back-side" attack at the ring carbon bound to oxygen is sterically unfavorable.

PTS: 1

  1. ANS:

PTS: 1

19. ANS:

PTS: 1

20. ANS:

d

PTS: 1

  1. ANS:

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

35. ANS:

PTS: 1

36. ANS:

PTS: 1

37. ANS:

PTS: 1

38. ANS:

PTS: 1

39. ANS:

PTS: 1

40. ANS:

Ethyl hexyl ether or 1-ethyoxyhexane

PTS: 1

  1. ANS: o- mercaptotoluene

PTS: 1

  1. ANS:

PTS: 1

43. ANS: