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Chapter 22: Problem 67

How would you synthesize each of the following? a. 1,2 -dibromopropane from propene b. acetone (2-propanone) from an alcohol c. tert-butyl alcohol (2-methyl-2-propanol) from an alkene (See Exercise 62.) d. propanoic acid from an alcohol

Short Answer

Expert verified
a. Add bromine (Br2) to propene in a CCl4 solution, forming 1,2-dibromopropane (CH2Br-CHBr-CH3). b. Oxidize 2-propanol using an oxidizing agent such as KMnO4 or H2CrO4, forming acetone (CH3-C(=O)-CH3). c. Perform a hydroboration-oxidation reaction with isobutene using borane (BH3) as the hydroborating agent and hydrogen peroxide (H2O2) in basic conditions, forming tert-butyl alcohol (CH3)3C-OH. d. First, oxidize propanol to propanal using a mild oxidizing agent. Then, oxidize propanal to propanoic acid using a stronger oxidizing agent like KMnO4 or HNO3.

Step by step solution

01

Reaction with bromine (Br2)

Add bromine (Br2) to propene (CH2=CH-CH3) in a solution of carbon tetrachloride (CCl4). This will result in an anti-addition reaction, with both bromine atoms adding to the double bond, forming 1,2-dibromopropane (CH2Br-CHBr-CH3). b. Synthesis of acetone (2-propanone) from an alcohol
02

Identify the starting alcohol

To synthesize acetone, we need to start with a secondary alcohol. In this case, we need 2-propanol (CH3-CH(OH)-CH3).
03

Oxidation of 2-propanol

Oxidize 2-propanol using an oxidizing agent such as potassium permanganate (KMnO4) or chromic acid (H2CrO4). This will transform the secondary alcohol into a ketone, which is acetone (CH3-C(=O)-CH3). c. Synthesis of tert-butyl alcohol (2-methyl-2-propanol) from an alkene
04

Identify the starting alkene

Synthesize tert-butyl alcohol from isobutene (CH2=C(CH3)2).
05

Hydroboration-oxidation of isobutene

Perform a hydroboration-oxidation reaction with isobutene using borane (BH3) as the hydroborating agent and hydrogen peroxide (H2O2) in basic conditions (e.g., NaOH) as the oxidizing agent. This results in tert-butyl alcohol (CH3)3C-OH. d. Synthesis of propanoic acid from an alcohol
06

Identify the starting alcohol

Identify the starting alcohol: propanol (CH3-CH2-CH2OH).
07

Oxidation of propanol to propanal

Oxidize propanol using a mild oxidizing agent, such as copper catalyst and oxygen gas or pyridinium chlorochromate (PCC). The primary alcohol will first be converted to an aldehyde, specifically propanal (CH3-CH2-C(=O)H).
08

Oxidation of propanal to propanoic acid

Using a stronger oxidizing agent, like potassium permanganate (KMnO4) or nitric acid (HNO3), oxidize propanal to form propanoic acid (CH3-CH2-C(=O)OH).

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Most popular questions from this chapter

Give the structure for each of the following. a. 4 -methyl-1-pentyne b. \(2,3,3\) -trimethyl-1-hexene c. 3 -ethyl-4-decene

Three different organic compounds have the formula \(\mathrm{C}_{3} \mathrm{H}_{8} \mathrm{O}\). Only two of these isomers react with \(\mathrm{KMnO}_{4}\) (a strong oxidizing agent). What are the names of the products when these isomers react with excess \(\mathrm{KMnO}_{4}\) ?

Reagents such as \(\mathrm{HCl}, \mathrm{HBr}\), and \(\mathrm{HOH}\left(\mathrm{H}_{2} \mathrm{O}\right)\) can add across carbon- carbon double and triple bonds, with \(\mathrm{H}\) forming a bond to one of the carbon atoms in the multiple bond and \(\mathrm{Cl}, \mathrm{Br}\), or OH forming a bond to the other carbon atom in the multiple bond. In some cases, two products are possible. For the major organic product, the addition occurs so that the hydrogen atom in the reagent attaches to the carbon atom in the multiple bond that already has the greater number of hydrogen atoms bonded to it. With this rule in mind, draw the structure of the major product in each of the following reactions. a. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}+\mathrm{H}_{2} \mathrm{O} \stackrel{\mathrm{H}^{*}}{\longrightarrow}\) b. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}+\mathrm{HBr} \longrightarrow\) c. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CH}+2 \mathrm{HBr} \longrightarrow\) d. CC1=CCCC1 e. Cl CC=C(C)CC

Give two examples of saturated hydrocarbons. How many other atoms are bonded to each carbon in a saturated hydrocarbon?

Draw all the structural and geometrical (cis-trans) isomers of bromochloropropene.
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