Tag: Multistep Mechanisms

Surprising Scores in Unit 4

At the end of the semester the students are typically burned out, busy with all of their final assignments, and in general do not perform as well on the last unit exam compared to the other three units. At Old Dominion University we teach addition to alkenes and alkynes in the last unit, a very

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Free Energy Diagrams Help Free Students from Memorization

Most organic professors can agree that we want our students to understand concepts and big pictures rather than memorize a list of facts. When determining the outcome or major product of a reaction, I’ve found that using free energy diagrams is a great way to facilitate concept based understanding over memorization. But despite their long-term

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Chapter 7: Elementary Steps but Giant Conceptual Leaps

If writing mechanisms is like giving good directions, then each elementary step is similar to saying “turn left at the stop sign.”  You might have to turn right many times during one trip just as you might need multiple acid-base steps during one mechanistic pathway. Joel’s “Most Common Elementary Steps” chapter lays out each possible

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Is Learning Organic Chemistry like Learning a New Language?

Over the years, I’ve heard many organic faculty use the phrase: “Learning organic chemistry is like learning a foreign language.” I’ve certainly used the phrase myself to give advice to my own students, in an attempt to convey that both subjects are cumulative and require a lot of practice. This year, however, I find myself

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Why a Mechanistic Organization Improves Understanding in Large Lectures

One of my favorite TV commercials is the AT&T, “Bigger is Better, It’s Not that Complicated” ad that features unscripted responses of elementary school children about why faster, bigger, larger, etc. is better.  Unlike cell coverage, bigger lecture size is not necessarily better. Over the years, I have done a number of things to make

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The Organization Makes Mechanisms Part of the Routine

A number of years ago I had a student come to me at the end of Organic II and ask, “What happened to the SN2 reaction?” She wanted to know why we had spent so much time on this one reaction in order to move on to the next unit and then never discussed this

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Practice Makes Permanent

Golf can frustrate my husband more than any other sport he plays. He recently asked a friend, who is a golf instructor, how to improve his game. The friend responded by saying that, “Practice does not make perfect, practice makes permanent.” If you are practicing with errors, it does not matter how much you practice,

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Improvements on Retrosynthetic Analysis

Success in organic chemistry is heavily reliant on a student’s ability to identify patterns. Until recently, I organized my course by functional group. It was only after I adopted Joel Karty’s approach that I recognized that the variety of reactions used to synthesize each functional group can vary widely and that this variance makes it

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The Benefits of a Mechanistically Organized Book When Teaching a 2-cycle Approach

Two-cycle organic chemistry is a pedagogical approach that has gained in popularity over the last couple decades. It’s a rather simple idea: The first semester course is treated as something of a survey, dealing primarily with the fundamentals, whereas the second semester revisits many of the same topics from the first semester, but treating them

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Chemical Intuition and the Reasonableness of Mechanisms

Each year, after I teach my class the overview of the ten most-common elementary steps, I feel a great sense of satisfaction because I begin to see students mastering two critical aspects of elementary steps: Drawing curved arrows in the correct way, and correctly predicting products when they are told which step occurs. But after

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