Bundle: Introduction to General, Organic and Biochemistry, 11th + OWLv2, 4 terms (24 months) Printed Access Card
Bundle: Introduction to General, Organic and Biochemistry, 11th + OWLv2, 4 terms (24 months) Printed Access Card
11th Edition
ISBN: 9781305705159
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
Question
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Chapter 14, Problem 14.37P
Interpretation Introduction

Interpretation:

The reagents and experimental condition should be shown to synthesize each compound given in the diagram from 1-propanol.

Bundle: Introduction to General, Organic and Biochemistry, 11th + OWLv2, 4 terms (24 months) Printed Access Card, Chapter 14, Problem 14.37P , additional homework tip  1

Concept Introduction:

Chemical reaction is the procedure to transform the chemical substance in the new substance. During this procedure sometimes, acid is involved which is the substance which could either accept electron pairs or donate protons in the reactions.

A catalyst is the molecule which is used to speed up the chemical reaction, not being consumed within the procedure. Acids are used as catalysts are needed for an acid catalyzed hydration.

A dehydration reaction is aeration when any organic substance loses the water molecule to form an alkene.

Expert Solution & Answer
Check Mark

Answer to Problem 14.37P

  1. Dehydration- Conc. H2SO4 at 180 C
  2. Hydration- dil. H2SO4
  3. Oxidation- K2Cr2O7, H2SO4
  4. Hydrobromination- HBr
  5. Bromination- Br2
  6. Hydrogenation- H2, Pt/Pd
  7. Oxidation- K2Cr2O7, H2SO4
  8. Oxidation- K2Cr2O7, H2SO4
  9. Oxidation- K2Cr2O7, H2SO4

Explanation of Solution

The reactions which are involved to synthesize each molecule are shown in the below diagram:

Bundle: Introduction to General, Organic and Biochemistry, 11th + OWLv2, 4 terms (24 months) Printed Access Card, Chapter 14, Problem 14.37P , additional homework tip  2

The reagents and experimental condition for each reaction are described below:

  1. Alcohols get converted into their corresponding alkenes through dehydration reaction. Water is formed from the hydroxyl group and hydrogen in the adjacent carbon. Primary alcohols get dehydrated at higher temperatures and in the presence of a strong acid, like sulfuric acid.
  2. Bundle: Introduction to General, Organic and Biochemistry, 11th + OWLv2, 4 terms (24 months) Printed Access Card, Chapter 14, Problem 14.37P , additional homework tip  3

  3. The hydration of an alkene in the presence of an acid like sulfuric acid puts the secondary alcohol in accordance with Markovnikov’s rule. According to the Markovnikov’s rule, the proton of the reagents gets added to the least substituted carbon while the remaining part of the reagent gets added to the most substituted carbon.
  4. Bundle: Introduction to General, Organic and Biochemistry, 11th + OWLv2, 4 terms (24 months) Printed Access Card, Chapter 14, Problem 14.37P , additional homework tip  4

  5. The oxidation of a secondary alcohol by using potassium dichromate and sulfuric acid gives the corresponding ketone.
  6. Bundle: Introduction to General, Organic and Biochemistry, 11th + OWLv2, 4 terms (24 months) Printed Access Card, Chapter 14, Problem 14.37P , additional homework tip  5

  7. The hydrobromination of an alkene by using hydrogen bromide puts the corresponding 2-bromopropane in accordance with Markovnikov’s rule. According to the Markovnikov’s rule, the proton of the reagent gets added to the least substituted carbon while the remaining part of the reagent gets added to the most substituted carbon.
  8. Bundle: Introduction to General, Organic and Biochemistry, 11th + OWLv2, 4 terms (24 months) Printed Access Card, Chapter 14, Problem 14.37P , additional homework tip  6

  9. The bromination of an alkene with bromine gives vicinal dibromo alkanes.
  10. Bundle: Introduction to General, Organic and Biochemistry, 11th + OWLv2, 4 terms (24 months) Printed Access Card, Chapter 14, Problem 14.37P , additional homework tip  7

  11. The hydrogenation of an alkene with hydrogen in the presence of a catalyst, like raney nickel, palladium or platinum, at a high temperature and pressure gives the corresponding alkane.
  12. Bundle: Introduction to General, Organic and Biochemistry, 11th + OWLv2, 4 terms (24 months) Printed Access Card, Chapter 14, Problem 14.37P , additional homework tip  8

  13. The oxidation of a primary alcohol by using potassium dichromate and sulfuric acid gives corresponding carboxylic acid. An intermediate aldehyde is formed in the reaction and is converted into corresponding carboxylic acid if it is not distilled out from the reaction mixture.
  14. Bundle: Introduction to General, Organic and Biochemistry, 11th + OWLv2, 4 terms (24 months) Printed Access Card, Chapter 14, Problem 14.37P , additional homework tip  9

  15. The oxidation of a primary alcohol by using potassium dichromate and sulfuric acid gives an aldehyde and should be distilled out from the reaction mixture to avoid getting further converted into the corresponding carboxylic acid.
  16. Bundle: Introduction to General, Organic and Biochemistry, 11th + OWLv2, 4 terms (24 months) Printed Access Card, Chapter 14, Problem 14.37P , additional homework tip  10

  17. The oxidation of an aldehyde by using potassium dichromate and sulfuric acid gives the corresponding carboxylic acid.
  18. Bundle: Introduction to General, Organic and Biochemistry, 11th + OWLv2, 4 terms (24 months) Printed Access Card, Chapter 14, Problem 14.37P , additional homework tip  11

Conclusion

Thus, the process and reagent used are as follows:

  1. Dehydration- Conc. H2SO4 at 180 C
  2. Hydration- dil. H2SO4
  3. Oxidation- K2Cr2O7, H2SO4
  4. Hydrobromination- HBr
  5. Bromination- Br2
  6. Hydrogenation- H2, Pt/Pd
  7. Oxidation- K2Cr2O7, H2SO4
  8. Oxidation- K2Cr2O7, H2SO4
  9. Oxidation- K2Cr2O7, H2SO4

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Chapter 14 Solutions

Bundle: Introduction to General, Organic and Biochemistry, 11th + OWLv2, 4 terms (24 months) Printed Access Card

Ch. 14 - 14-11 Which of the alcohols in Problem 14-10 are...Ch. 14 - 14-12 Write the 1UPAC name of each compound. (e)...Ch. 14 - Prob. 14.13PCh. 14 - Prob. 14.14PCh. 14 - 14-15 Both alcohols and phenols contain an —OH...Ch. 14 - Prob. 14.16PCh. 14 - 14-17 Explain in terms of noncovalent interactions...Ch. 14 - Prob. 14.18PCh. 14 - Prob. 14.19PCh. 14 - 14-20 Show hydrogen bonding between methanol and...Ch. 14 - 14-21 Show hydrogen bonding between the oxygen of...Ch. 14 - 14-22 Arrange these compounds in order of...Ch. 14 - 14-23 Arrange these compounds in order of...Ch. 14 - 14-24 2-Propanol (isopropyl alcohol) is commonly...Ch. 14 - 14-25 Explain why glycerol is much thicker (more...Ch. 14 - Prob. 14.26PCh. 14 - Prob. 14.27PCh. 14 - 14-28 Give the structural formula of an alkene or...Ch. 14 - Prob. 14.29PCh. 14 - 14-30 Show how to distinguish between cyclohexanol...Ch. 14 - 14-31 Compare the acidity of alcohols and phenols,...Ch. 14 - 14-32 Both 2,6-diisopropylcyclohexanol and the...Ch. 14 - 14-33 Write equations for the reaction of...Ch. 14 - 14-34 Write equations for the reaction of...Ch. 14 - 14-35 Write equations for the reaction of each of...Ch. 14 - 14-36 Show how to convert cyclohexanol to these...Ch. 14 - Prob. 14.37PCh. 14 - Prob. 14.38PCh. 14 - 14-39 Name two important alcohols derived from...Ch. 14 - 14-40 Name two important alcohols derived from...Ch. 14 - Prob. 14.41PCh. 14 - 14-42 Write the common name for each ether. ch3...Ch. 14 - Prob. 14.43PCh. 14 - 14-44 Answer true or false. (a) The functional...Ch. 14 - Prob. 14.45PCh. 14 - Prob. 14.46PCh. 14 - 14-47 Following are structural formulas for...Ch. 14 - 14-48 Explain why methanethiol, CH3SH, has a lower...Ch. 14 - 14-49 Answer true or false. Today, the major...Ch. 14 - Prob. 14.50PCh. 14 - 14-51 (Chemical Connections 14B) When was...Ch. 14 - 14-52 (Chemical Connections 14B) What was Alfred...Ch. 14 - Prob. 14.53PCh. 14 - 14-54 (Chemical Connections 14C) What is the color...Ch. 14 - 14-55 (Chemical Connections 140 The legal...Ch. 14 - 14-56 (Chemical Connections 14D) What does it mean...Ch. 14 - 14-57 (Chemical Connections 14E) What are the...Ch. 14 - Prob. 14.58PCh. 14 - Prob. 14.59PCh. 14 - 14-60 Write a balanced equation for the complete...Ch. 14 - 14-61 Knowing what you do about electronegativity,...Ch. 14 - 14-62 Draw structural formulas and write IUPAC...Ch. 14 - Prob. 14.63PCh. 14 - 14-64 Explain why the boiling point of ethylene...Ch. 14 - Prob. 14.65PCh. 14 - 14-66 1,4-Butanediol, hexane, and 1-pentanol have...Ch. 14 - 14-67 Of the three compounds given in Problem...Ch. 14 - Prob. 14.68PCh. 14 - 14-69 Show how to prepare each compound from...Ch. 14 - 14-70 Show how to prepare each compound from...Ch. 14 - 14-71 The mechanism of the acid-catalyzed...Ch. 14 - Prob. 14.72PCh. 14 - 14-73 Lipoic acid is a growth factor for many...Ch. 14 - 14-74 Following is a structural formula for the...Ch. 14 - Prob. 14.75PCh. 14 - Prob. 14.76PCh. 14 - Prob. 14.77PCh. 14 - 14-78 Consider alkenes A, B, and C. each of which...Ch. 14 - Prob. 14.79P
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