What reaction occurs when CH3CH2OH is treated with (a) H2SO4? (b) NaH? What happens when CH3CH3

step 1 This is the answer to Chapter 3, problem number one, from the Smith Organic Chemistry textbook.

What reaction occurs when CH3CH2OH is treated with (a)...

Key Concepts

Acid-Catalyzed Dehydration

This concept involves the reaction of an alcohol with a strong acid like sulfuric acid to form an alkene. The process is initiated by the protonation of the hydroxyl group, making it a better leaving group. Subsequent elimination (often E1 mechanism in secondary or tertiary alcohols, and sometimes E2 in primary alcohols under careful conditions) results in the loss of water and formation of a carbon–carbon double bond. This reaction is particularly common with alcohols that can stabilize the intermediate carbocation formed during the process.

Formation of Alkoxides via Deprotonation

When an alcohol reacts with a strong base such as sodium hydride (NaH), the acidic hydrogen in the hydroxyl group is abstracted to form an alkoxide ion. This deprotonation reaction generates a reactive nucleophile that can participate in further reactions like nucleophilic substitution, for example in the Williamson ether synthesis. The alkoxide formation is a key step in many synthetic transformations, showcasing how base-mediated deprotonation can alter the reactivity of organic molecules.

Acidity and Reactivity Differences between Alcohols and Alkanes

This key concept highlights the difference in reactivity between molecules bearing acidic protons, such as alcohols, and those that lack them, like alkanes. Alcohols contain a hydroxyl group with a hydrogen that is relatively acidic and can be removed by strong bases, leading to reactive intermediates like alkoxides. In contrast, alkanes do not have such acidic hydrogens and are generally inert under conditions that promote deprotonation or acid-catalyzed dehydration, explaining why they remain unreactive when exposed to reagents like H?SO? and NaH.

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