Excellent question. If you break down exams, then you will notice a good number of these types of questions. They are deceptively challenging and in all likelihood have some of the lowest raw scores of the different question types. One of the things we tell our students in class is that different question types require different approaches. Many, many people make the massive mistake of focusing on content in their studies and never realize how important it is to do exactly what you just did: ask about a style of question and an algorithm to solve it.
For that type of question, one of the biggest errors people tend to make is second-guessing themselves based on special cases they create to fit an answer choice. As you consider each choice, ask yourself if you are making a "special case" to make that answer correct. If you are, then it is likely not the best answer. Second-guessing both wastes time and often leads you farther from a best answer rather than get you closer.
Consider the following question.
Q. What is the most likely explanation for the broadness of the IR signal at 3461 cm-1 for 3-methylcyclo-2-pentenol being broader than the IR signal at 3482 cm-1 for 1-methylcyclo-2-pentenol?
A. Resonance of the hydroxyl is maximized by ring structures.
B. Steric hindrance prevents the structures from getting as close together to form a strong hydrogen bond.
C. Alkyl groups donate electron density to nearby substituents and make them better electron pair donors.
D. Ring structures experience the least entropy when they have substituents on the same carbon in the ring.
This is an easy question to get lost in tempting wrong answers. You need to make strong decisions and stick to them. Resonance of a hydroxyl lone pair into a π-bond is not impacted by ring structures unless there is ring strain (causing poor π-orbital overlap), so choice A should be eliminated and forgotten. Steric hindrance is a valid explanation for two structures not getting close enough to form a strong H-bond, so tertiary alcohols would have narrower hydroxyl absorbances than secondary alcohols due to less H-bonding. Choice B is still standing and we used a generic explanation, not a special case, so it is looking like a good choice. Choice C is a completely true but irrelevant answer that can suck up your time. Alkyl groups do donate electron density through the inductive effect, and that can definitely impact nearby substituents. However, that is not the best explanation here, as the methyl is not impacting the hydroxyl group. Choice C must eliminated and not considered again. Ring structures have reduced entropy, but again, that is irrelevant to the question. This becomes another potential time sink if you overthink it. Adding substituents may or may not affect the entropy, but that ultimately has no impact on the broadness of the IR signal. Only choice B is a generic statement that explains the observation.
The biggest advice is to make strong decisions, avoid special cases, recognize when an answer is irrelevant to the question, and refuse to question yourself once you have made your choice.
Good luck!
