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Chapter 17: Problem 95

How can you convert \(\mathrm{R}-\mathrm{Cl}\) to \(\mathrm{R}-\mathrm{OH}\) ?

Short Answer

Expert verified
To convert an alkyl chloride (R-Cl) to an alcohol (R-OH), use a nucleophilic substitution reaction (SN2 mechanism) with hydroxide ions (OH-) as the nucleophile. The overall reaction is: \[ R-Cl + OH^- \rightarrow R-OH + Cl^- \] Ensure the alkyl chloride is primary (1º) or secondary (2º), and use a solution of aqueous sodium hydroxide (NaOH) or potassium hydroxide (KOH) as the reagent.

Step by step solution

01

Identify the reaction for converting R-Cl to R-OH

The nucleophilic substitution reaction (specifically, the SN2 mechanism) can be used to convert an alkyl chloride (R-Cl) to an alcohol (R-OH). In this case, we can react the alkyl chloride with a hydroxide ion (OH-) as the nucleophile.
02

Understand the mechanism of the SN2 reaction

In an SN2 reaction, the nucleophile (OH-) attacks the electrophilic carbon atom (the carbon atom attached to the chlorine) from the opposite side of the leaving group (Cl-). This results in the inversion of the chiral center (if there is one) and the formation of the alcohol (R-OH).
03

Write the overall reaction

The overall reaction can be written as follows: \[ R-Cl + OH^- \rightarrow R-OH + Cl^- \]
04

Condition for the SN2 reaction

Ensure that the alkyl chloride is primary (1º) or secondary (2º) for the SN2 reaction to occur. Tertiary (3º) alkyl halides generally do not undergo SN2 reactions.
05

Identify the reagents and conditions

The most common reagent to use in this conversion is a solution of aqueous sodium hydroxide (NaOH) or potassium hydroxide (KOH). These strong bases will provide the necessary hydroxide ions (OH-) for the nucleophilic substitution reaction to occur.

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Most popular questions from this chapter

Where do we start numbering carbons on a main chain when both branches and \(C=C\) or \(C \equiv C\) bonds are present?

Give the line drawing and molecular formula for: (a) 3 -methylpentane (b) 2,3 -dimethyl-2-butene (c) 3 -methyl-1-pentene (d) 5 -methyl-1-hexyne

Do propane, propene, and propyne belong to a homologous series? Explain.

Using the molecular formula \(\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{Cl}_{2}\), draw the structural formula of (a) a molecule that is polar, (b) a molecule that is nonpolar, and (c) a molecule that contains only \(\mathrm{C}-\mathrm{C}\) single bonds.

What class of compounds does the general formula \(\mathrm{R}-\mathrm{OH}\) represent? What does the \(\mathrm{R}\) represent?
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