(••••) Hoping to make the following diene, a chemist treated the diol shown with acid. Based on the IR spectrum, was the reaction successful? If not, what compound was made instead? [You studied this reaction in Chapter 13.]

Verified step by step guidance

1. Identify the starting material: The problem mentions a diol, which is a compound containing two hydroxyl (OH) groups.
2. Understand the reaction conditions: The diol is treated with acid, which suggests a dehydration reaction might occur, potentially forming a diene.
3. Analyze the IR spectrum: Look for the presence or absence of key functional group signals. A successful conversion to a diene would show a decrease or absence of OH stretch (around 3200-3600 cm^-1) and the presence of C=C stretches (around 1600-1680 cm^-1).
4. Consider alternative products: If the IR spectrum does not show the expected signals for a diene, consider what other products could form under acidic conditions, such as ethers or rearranged alcohols.
5. Conclude based on IR data: Determine if the reaction was successful in forming the diene or if another compound was formed, based on the presence or absence of characteristic IR peaks.

Key Concepts

Diels-Alder Reaction

The Diels-Alder reaction is a cycloaddition reaction between a conjugated diene and a dienophile, forming a six-membered ring. This reaction is a key method in organic synthesis for constructing cyclic compounds and is characterized by its stereospecificity and regioselectivity. Understanding this reaction is crucial for predicting the products formed when treating a diene with acid.

Infrared (IR) Spectroscopy

Infrared spectroscopy is an analytical technique used to identify functional groups in organic compounds by measuring the absorption of infrared light. Different bonds absorb characteristic frequencies of IR radiation, allowing chemists to deduce the presence of specific functional groups. Analyzing the IR spectrum can help determine whether the desired diene was formed or if another compound resulted from the reaction.

Acid-Catalyzed Dehydration

Acid-catalyzed dehydration is a reaction where an alcohol is converted into an alkene through the removal of water, typically facilitated by an acid. This process often involves the formation of a carbocation intermediate, which can lead to rearrangements or side reactions. Recognizing this mechanism is essential for understanding what compound may have been produced instead of the intended diene when the diol is treated with acid.