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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
To synthesize 1,2-dibromopropane from propene, perform electrophilic addition with Br2 to obtain 2-bromopropane, and then nucleophilic substitution with Br- to form 1,2-dibromopropane. To synthesize acetone from an alcohol, oxidize isopropyl alcohol using K2Cr2O7 or KMnO4. For tert-butyl alcohol from an alkene, hydrate 2-methylpropene with strong acid. Lastly, to synthesize propanoic acid from an alcohol, oxidize 1-propanol using K2Cr2O7 or KMnO4 to form propanoic acid.

Step by step solution

01

Bromination of propene

To synthesize 1,2-dibromopropane from propene, we must first brominate the double bond of the propene molecule. This can be done by adding bromine (Br2) and performing an electrophilic addition reaction. The reaction will follow Markovnikov's rule, adding the first bromine atom to the more substituted carbon, creating a 2-bromopropane intermediate.
02

Nucleophilic substitution of 2-bromopropane

To add the second bromine atom to the molecule, we must perform a nucleophilic substitution reaction. This involves treating the 2-bromopropane intermediate with a good nucleophile such as the bromide ion (Br-) in the presence of a polar aprotic solvent. This will result in the formation of 1,2-dibromopropane. b. Synthesis of acetone (2-propanone) from an alcohol
03

Oxidation of isopropyl alcohol

To synthesize acetone from an alcohol, we must perform oxidation of the alcohol group. Specifically, we want to oxidize isopropyl alcohol (2-propanol). This can be achieved by treating the alcohol with an oxidizing agent, such as potassium dichromate (K2Cr2O7) or potassium permanganate (KMnO4). This will yield acetone (2-propanone) as the main product. c. Synthesis of tert-butyl alcohol (2-methyl-2-propanol) from an alkene
04

Hydration of the alkene

To synthesize tert-butyl alcohol from an alkene, we'll start with 2-methylpropene (isobutylene) as our starting material. We must perform a hydration reaction, which involves adding water to the double bond in the presence of a strong acid catalyst (concentrated sulfuric acid or phosphoric acid). This reaction follows Markovnikov's rule and will produce tert-butyl alcohol (2-methyl-2-propanol). d. Synthesis of propanoic acid from an alcohol
05

Oxidation of 1-propanol

To synthesize propanoic acid from an alcohol, we must perform the oxidation of 1-propanol (n-propyl alcohol). This can be achieved by treating the alcohol with a strong oxidizing agent, such as potassium dichromate (K2Cr2O7) or potassium permanganate (KMnO4). After the oxidation reaction, the primary alcohol is first converted to an aldehyde (propanal) and then to propanoic acid (a carboxylic acid) as the final product.

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Most popular questions from this chapter

A chemical "breathalyzer" test works because ethanol in the breath is oxidized by the dichromate ion (orange) to form acetic acid and chromium(III) ion (green). The balanced reaction is \(3 \mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}(a q)+2 \mathrm{Cr}_{2} \mathrm{O}_{7}^{2-}(a q)+2 \mathrm{H}^{+}(a q) \longrightarrow\) \(3 \mathrm{HC}_{2} \mathrm{H}_{3} \mathrm{O}_{2}(a q)+4 \mathrm{Cr}^{3+}(a q)+11 \mathrm{H}_{2} \mathrm{O}(l)\) You analyze a breathalyzer test in which \(4.2 \mathrm{mg} \mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}\) was reduced. Assuming the volume of the breath was \(0.500 \mathrm{~L}\) at \(30 .{ }^{\circ} \mathrm{C}\) and \(750 . \mathrm{mm} \mathrm{Hg}\), what was the mole percent alcohol of the breath?

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 \(\mathrm{KMnO}_{4} ?\)

Cumene is the starting material for the industrial production of acetone and phenol. The structure of cumene is Give the systematic name for cumene.

Explain why methyl alcohol is soluble in water in all proportions, while stearyl alcohol \(\left[\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{16} \mathrm{OH}\right]\) is a waxy solid that is not soluble in water.

Draw the following. a. cis \(-2\) -hexene b. trans-2-butene c. cis-2,3-dichloro-2-pentene
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