Chapter 12: Problem 5
The reagent used for the following conversion: \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}\) is (a) \(\mathrm{LiAlH}_{4}\) (b) Amalgamated zinc and concerntrated \(\mathrm{HCl}\) (c) Red phosphorus and concentrated HI (d) Soda lime
Short Answer
Step by step solution
Identify the Reaction Type
Determine Suitable Reagent
Analyze Options
Select the Correct Reagent
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Wolff-Kishner Reduction
This reaction starts with the formation of a hydrazone from the carbonyl compound, which then undergoes decompose under heat and basic conditions to result in the alkane and nitrogen gas. Understanding this process is crucial because it highlights a targeted method to modify carbon structures, effectively replacing double-bonded oxygen atoms by hydrogen atoms.
However, important to note, Wolff-Kishner Reduction is not suitable for converting carboxylic acids directly to alkanes, as it requires a specific type of carbonyl group, usually ketones or aldehydes.
Clemmensen Reduction
Clemmensen Reduction works well on ketones and aldehydes, reducing these functional groups to produce alkanes. However, similar to the limitations observed in the Wolff-Kishner Reduction, Clemmensen Reduction is not directly applicable to carboxylic acids. The acidic medium would not suit the stability of carboxylic groups, necessitating alternative routes for reduction.
Students studying these methods should appreciate the complementary nature of Clemmensen and Wolff-Kishner reductions, allowing chemists to choose a reaction pathway based on their specific substrate and experimental conditions.
Carboxylic Acids
These compounds are versatile and show broad reactivity patterns, making them integral to many synthetic and naturally occurring processes. However, directly converting carboxylic acids to simpler hydrocarbons such as alkanes typically requires special reagents and methods.
The conversion involves decarboxylation and often requires special conditions or additional reagents such as red phosphorus and concentrated HI, which facilitate the replacement of the carboxyl group with hydrogen, ultimately forming an alkane.
Alkane Formation
To form an alkane, the functional group \(\text{-COOH}\) in carboxylic acids must be reduced and entirely removed, often through decarboxylation processes. Though challenging, one effective method is using red phosphorus and concentrated HI to accomplish this conversion, as it can efficiently replace the carboxyl group with hydrogen atoms, producing a simpler alkane chain.
A firm grasp of the concepts underpinning alkane formation is beneficial, not only due to the alkanes' importance as fuels and raw materials but also due to their prevalence in many biological systems and industrial applications. Understanding the mechanisms to synthesize them can be remarkably useful in both academic and practical settings.