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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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