For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.
(a)

검증된 단계별 안내

Step 1: Identify the functional groups in the molecule. The molecule contains a terminal alkyne (-C≡CH) and an alcohol (-OH) group.

Step 2: Recognize the reactivity of the functional groups with a strong base. A strong base can deprotonate acidic hydrogens. Terminal alkynes have acidic hydrogens due to the sp-hybridized carbon, and alcohols can also be deprotonated, but the terminal alkyne hydrogen is more acidic.

Step 3: Determine which hydrogen will be removed. The terminal alkyne hydrogen is more acidic (pKa ~25) compared to the alcohol hydrogen (pKa ~16), so the base will preferentially deprotonate the terminal alkyne.

Step 4: Write the product of the reaction. Deprotonation of the terminal alkyne will result in the formation of an alkynide ion (R-C≡C⁻), where R represents the rest of the molecule.

Step 5: Consider the stability of the product. The alkynide ion is stabilized by the strong base, and no further reaction occurs unless additional reagents are introduced.

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Strong Bases in Organic Chemistry

Strong bases, such as sodium hydroxide (NaOH) or potassium tert-butoxide (KOtBu), are capable of deprotonating weak acids, including alcohols. In organic reactions, they can facilitate the formation of alkoxides by removing a proton from the hydroxyl (-OH) group, leading to increased nucleophilicity and reactivity of the resulting alkoxide.

Deprotonation Mechanism

Deprotonation is the process where a proton (H+) is removed from a molecule, often resulting in the formation of a negatively charged species. In the context of alcohols reacting with strong bases, the base abstracts the proton from the hydroxyl group, converting the alcohol into an alkoxide ion, which can then participate in further reactions, such as nucleophilic substitution or elimination.

Reaction Products of Alcohols with Bases

When an alcohol reacts with a strong base, the primary product is typically an alkoxide ion. Depending on the structure of the alcohol and the reaction conditions, this alkoxide can further react with electrophiles or participate in elimination reactions, leading to the formation of alkenes or other functional groups. Understanding the structure of the starting material is crucial for predicting the specific products formed.

For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.(a)