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Chapter 12: PROBLEM 12.24 (page 479)

Question: Draw the organic products in each of the following reactions.

a.

b.

c.

d.

Short Answer

Expert verified

Answer

a.

b.

c.

d.

Step by step solution

01

Oxidation using alcohols

Alcohols can be oxidized into ketones, aldehydes, or carboxylic acids using strong oxidizing agents.

The reactions of different types of alcohols with oxidizing agents are given below:

Oxidation of alcohols

02

Reagents

The reagents that are mostly used are PCC, CrO3 ,H2SO4 /H2SO4, K2Cr2O7

CrO3and K2Cr2O7 are stronger oxidizing agents and are therefore used to convert primary alcohols to carboxylic acids. Secondary alcohols are reactive to all of the reagents.

03

Determining the organic products

a. The given compound is a primary alcohol, which when oxidized with PCC, would produce an aldehyde, as shown below:

Oxidation of primary alcohol using PCC

b. As secondary alcohols get oxidized to form ketone in presence of any Cr6+ reagents, the product would be as shown below

Oxidation of secondary alcohol using PCC

c. When primary alcohol is reacted with , it will produce a carboxylic acid.

Oxidation of primary alcohol using CrO3

d. The secondary alcohol would react with to produce the following ketone.

Oxidation of secondary alcohol using

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Most popular questions from this chapter

Question: One compound that contributes to the “seashore smell”at beaches in Hawai’s is dictyopterene D’ with excess H2in the presence of a Pd catalyst forms butylcycloheptane. Ozonolysis with O3 followed by (CH3)2S forms CH2(CHO)2,HCOCH2CH(CHO)2, and CH3CH2CHO. What are possible structures of dictyopterene D’?

Question:Devise a synthesis of (3R,4S)-3,4-dichlorohexane from acetylene and any needed organic compounds or inorganic reagents.

Question: An unknown compound A of molecular formula C10H18O reacts with H2SO4 to form two compounds (B and C) of molecular formula C10H16. B and C both react with H2 in the presence of Pd-C to form decalin. Ozonolysis of B forms D, and ozonolysis of C forms a diketone E of molecular formula C10H16O2. Identify the structures of compounds A, B, C and E.

Question: Complete the missing information for compounds A, B, and C, each subjected to hydrogenation. The number of rings and π bonds refers to the reactant (A, B, or C) prior to hydrogenation.

Question: How many rings and π bonds are contained in compounds A–C? Draw one possible structure for each compound.

a. Compound A has molecular formula C5H8 and is hydrogenated to a compound having molecular formula C5H10.

b. Compound B has molecular formula C10H16 and is hydrogenated to a compound having molecular formula C10H18 .

c. Compound C has molecular formula C8H8 and is hydrogenated to a compound having molecular formula C8H16.
See all solutions

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