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. Brominate propene using Br2 to form 1,2-dibromopropane. \[ \text{Propene + Br}_2 \rightarrow \text{1,2-dibromopropane}\] b. Oxidize propan-2-ol using K2Cr2O7 and H2SO4 to form acetone (2-propanone). \[ \text{Propan-2-ol + K}_2\text{Cr}_2\text{O}_7 + \text{H}_2\text{SO}_4 \xrightarrow[]{\Delta} \text{2-propanone (acetone)}\] c. Hydrate 2-methylpropene using H2O and H2SO4 to form tert-butyl alcohol (2-methyl-2-propanol). \[ \text{2-Methylpropene} + \text{H}_2\text{O} + \text{H}_2\text{SO}_4 \rightarrow \text{tert-butyl alcohol (2-methyl-2-propanol)}\] d. Oxidize propan-1-ol using K2Cr2O7 and H2SO4 to form propanoic acid. \[ \text{Propan-1-ol} + 2 \, \text{K}_2\text{Cr}_2\text{O}_7 + 2 \, \text{H}_2\text{SO}_4 \xrightarrow[]{\Delta} \text{Propanoic acid}\]

Step by step solution

01

Bromination of propene

Add one equivalent of bromine (Br2) to the propene molecule. The bromination of an alkene is an electrophilic addition reaction. Br2 will add across the double bond of propene, forming 1,2-dibromopropane as the product. \[ \text{Propene + Br}_2 \rightarrow \text{1,2-dibromopropane}\] b. Synthesis of acetone (2-propanone) from an alcohol
02

Identify the precursor alcohol

Determine the alcohol precursor from which we can synthesize acetone. It is propan-2-ol, given that oxidation of this secondary alcohol will result in a ketone.
03

Oxidation of propan-2-ol

Oxidize propan-2-ol using an appropriate oxidizing agent, such as potassium dichromate (K2Cr2O7) and concentrated sulfuric acid (H2SO4), and then heat the solution. This reaction will transform the secondary alcohol into 2-propanone (acetone). \[ \text{Propan-2-ol + K}_2\text{Cr}_2\text{O}_7 + \text{H}_2\text{SO}_4 \xrightarrow[]{\Delta} \text{2-propanone (acetone)}\] c. Synthesis of tert-butyl alcohol (2-methyl-2-propanol) from an alkene
04

Identify the precursor alkene

Determine the alkene precursor from which we can synthesize tert-butyl alcohol. It is 2-methylpropene, given that hydration of this alkene will result in a tertiary alcohol.
05

Hydration of 2-methylpropene

Hydrate 2-methylpropene using water (H2O) in the presence of an acid catalyst, such as concentrated sulfuric acid (H2SO4) or phosphoric acid (H3PO4). This reaction will result in the formation of tert-butyl alcohol (2-methyl-2-propanol). \[ \text{2-Methylpropene} + \text{H}_2\text{O} + \text{H}_2\text{SO}_4 \rightarrow \text{tert-butyl alcohol (2-methyl-2-propanol)}\] d. Synthesis of propanoic acid from an alcohol
06

Identify the precursor alcohol

Determine the alcohol precursor from which we can synthesize propanoic acid. It is propan-1-ol, given that oxidation of this primary alcohol will result in a carboxylic acid.
07

Oxidation of propan-1-ol

Oxidize propan-1-ol using an appropriate oxidizing agent, such as potassium dichromate (K2Cr2O7) and concentrated sulfuric acid (H2SO4), and then heat the solution to reflux. This reaction will transform the primary alcohol into propanal (an aldehyde) first, followed by further oxidation into propanoic acid. \[ \text{Propan-1-ol} + 2 \, \text{K}_2\text{Cr}_2\text{O}_7 + 2 \, \text{H}_2\text{SO}_4 \xrightarrow[]{\Delta} \text{Propanoic acid}\]

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