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Q6.11(vi):
How will you bring about the following conversions? (vi) Ethanol to ethyl fluoride

Solution :

Step 1: Theoretical Analysis of the Conversion Path

The conversion of ethanol ($CH_3CH_2OH$) to ethyl fluoride ($CH_3CH_2F$) involves the replacement of a hydroxyl group ($-OH$) with a fluorine atom ($-F$). Because direct fluorination of alcohols is not feasible via simple nucleophilic substitution with $F^-$, a two-step transformation is required: [Per the limitations of nucleophilic substitution reactions in alcohols].

  • Step A: Convert the alcohol to an alkyl halide (specifically ethyl bromide or ethyl chloride) to introduce a better leaving group.
  • Step B: Perform a nucleophilic substitution (Swarts reaction) to replace the halide with fluorine.

Step 2: Step-by-Step Chemical Synthesis

Step 2.1: Conversion of Ethanol to Ethyl Bromide

Ethanol is treated with phosphorus tribromide ($PBr_3$) to yield ethyl bromide. Phosphorus halides are preferred over $HX$ to prevent side reactions like dehydration. [By nucleophilic substitution mechanism, specifically the conversion of primary alcohols to alkyl halides].

$3CH_3CH_2OH + PBr_3 \rightarrow 3CH_3CH_2Br + H_3PO_3$

Step 2.2: Conversion of Ethyl Bromide to Ethyl Fluoride (Swarts Reaction)

The ethyl bromide is subjected to the Swarts reaction, which uses metallic fluorides such as $AgF$, $Hg_2F_2$, $CoF_2$, or $SbF_3$. [Per the Swarts Reaction mechanism, where the halogen-fluorine exchange is driven by the formation of an insoluble metal halide precipitate].

$CH_3CH_2Br + AgF \rightarrow CH_3CH_2F + AgBr \downarrow$

Step 3: Visual Representation of the Synthetic Route

Ethanol PBr₃ Ethyl Bromide AgF Ethyl Fluoride

Step 4: Summary of Reaction Conditions

Reagent Reaction Type By-product
$PBr_3$ Nucleophilic Substitution $H_3PO_3$
$AgF$ Halogen Exchange (Swarts) $AgBr$

Final Solution: The conversion of ethanol to ethyl fluoride is achieved via a two-step process: first reacting ethanol with $PBr_3$ to form bromoethane, followed by the reaction of bromoethane with silver fluoride ($AgF$) to yield ethyl fluoride.


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