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Chapter 12: PROBLEM 12.25 (page 480)

Question: What carbonyl compound is formed when each alcohol is treated with HCrO4––Amberlyst A-26 resin?

a.

b.

c.

Short Answer

Expert verified

Answer

a.

b.

c.


Step by step solution

01

Green chemistry

The practice of substituting reagents that cause environmental toxicity with eco-friendly alternatives is known as green chemistry. Such reagents require lesser solvents and generate lesser waste products.

02

Amberlyst A-26 resin

Amberlyst A-26 resin is a polymeric reagent that acts as an eco-friendly alternative to toxic reagents such as chromic acid. They do not require solvents such as sulfuric acid to perform the oxidation reaction.

The reaction of the resin with different alcohols is shown below:

Application of Amberlyst resin as an oxidizing agent

03

Determination of the type of bond present

The bonds are classified as ionic or covalent based on atomic charges. Two neutral atoms will form a covalent bond, whereas two charged species will form an ionic bond.

04

Determination of product

a.

Oxidation of primary and secondary alcohols using Amberlyst A-26 resin

b.

Oxidation of secondary alcohol using Amberlyst A-26 resin

c.

Oxidation of primary alcohol using Amberlyst A-26 resin

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Most popular questions from this chapter

Question: Stearidonic acid (C18H28O2 ) is an unsaturated fatty acid obtained from oils isolated from hemp and blackcurrant (see also Problem 10.11).

a. What fatty acid is formed when Stearidonic acid is hydrogenated with excess H2 and a Pd catalyst?

b. What fatty acids are formed when stearidonic acid is hydrogenated with one equivalent of H2 and a Pd catalyst?

c. Draw the structure of a possible product formed when stearidonic acid is hydrogenated with one equivalent of H2 and a Pd catalyst, and one double bond is isomerized to a trans isomer.

d. How do the melting points of the following fatty acids compare: stearidonic acid; one of the products formed in part (b); the product drawn in part (c)?

Question: It is sometimes necessary to isomerize a cis alkene to a trans alkene in a synthesis, a process that cannot be accomplished in a single step. Using the reactions that you have learned in Chapters 8–12, devise a stepwise method to convert cis-but-2-ene to trans-but-2-ene.

Question: Draw the structure of two different epoxides that would yield 2-methylpentan-2-ol [ (CH3)2CH(OH)CH2CH2CH3] when reduced with LiAlH4 .

Question: Draw a stepwise mechanism for the reduction of epoxide A to alcohol B using LiAlH4 . What product would be formed if LiAlD4were used as reagent? Indicate the stereochemistry of all stereogenic centers in the product using wedges and dashed wedges.

Question: Epoxidation of the following allylic alcohol using the Sharpess reagent (-)-DET gives two epoxy alcohols in a ratio of 87:13.

  1. Assign structures to the major and minor product.
  2. What is the enantiomeric excess in this reaction?
See all solutions

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