akg - Copyright, Arizona State University Nucleophilic...

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Aldehydes and Ketones 1 Copyright, Arizona State University Copyright, Arizona State University Aldehydes and Ketones Nucleophilic Addition (more. ..) 1 Structure and Nomenclature Dipole Moment ~3.0D Nucleophilic end ( can protonate ) Electrophilic end (reacts with nucleophiles) ~1.8D H 3 C C O CH 3 δ δ OH H 3 C C O CH 3 • C=O Bond has Larger dipole moment than C–O bond because the pi-electrons are more polarizable IUPAC nomenclature uses numbering system Aldehydes - Suffix -al : Ketones - Suffix -one priority: aldehyde > ketone > alcohol > alkene > alkyne > halide (higher priority with higher oxidation) H 3 C CH Cl CH 2 CH 2 C O H 1 2 3 4 5 4-chloropentanal –CHO = C H O sterochemistry ignored • Above, no number for simple aldehyde, C=O must always be 1 H 3 C C CH 2 CH 2 O Cl 1 2 3 4 4-chloro-2-butanone • Above, number to give carbonyl smallest number CH 3 CH 2 C CH 2 CH H 3 C O OH 1 2 3 4 5 6 5-hydroxy-3-hexanone sterochemistry ignored • Above, ketone takes priority over alcohol O H 5-oxohexanal O 1 2 3 4 5 • Above, ketone lower priority than aldehyde, , use "oxo" when ketone is a subsituent O (6S)-chloro-hept-(3E)-en-2-one Cl 1 2 3 4 5 6 • Above, example of multiple suffixes
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Aldehydes and Ketones 2 Copyright, Arizona State University Copyright, Arizona State University Aldehydes/Ketones PROBLEMS Aldehyde/Ketone Nomenclature In each case, give the IUPAC name for the provided structure (ignore stereochemistry unless specified) 1 (easier) O Br Answer Correct Y / N 2 (standard) O Answer Correct Y / N 3 (standard) CHO Br Answer Correct Y / N 4 (standard) Br O H Answer Correct Y / N 5 (standard) H O O Answer Correct Y / N 6 (standard) O OH Cl Answer Correct Y / N Doing problems is the only way that you will learn organic chemistry. You should do problems in the notes, from the textbook and from problem sets. It is CRITICAL that you keep track of what you know and what you don't know. Each notes problem has a "Correct Y / N" box. When you are PROPERLY CONVINCED that you can do a problem, circle "Y", if you can't do the problem circle "N". Keep coming back to those problems with the circled "N", until you can circle the "Y". Here are some ways NOT TO DO PROBLEMS (and when NOT to circle "Y"). .. 1. You do them in a group, someone else in the group gets to the answer before you, you understand why the answer is correct, you therefore assume you can do that problem, you check "Y" 2. You do them on your own, you are not sure about the answer, you check it to see if you are right, you are, you check "Y" 3. You do a problem, it is similar to the one you just did, you look at the answer, you understand the answer, you check "Y" 4. You can't do a problem, you ask for help, you understand the answer, you check "Y" 5. You do a problem, you get it mainly correct, but a little bit wrong, you understand what you did wrong, you check "Y" UNDERSTANDING is different from DOING. In each of the above scenarios you have not proven that you can do the problem, rather you have proven that you CAN'T do the problem without help from others, or without "cheating" on the time it takes to do a problem, or without proving that you can do the problem 100% correct.
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This note was uploaded on 01/07/2012 for the course CHM 234 taught by Professor Iangould during the Spring '12 term at Appalachian State.

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akg - Copyright, Arizona State University Nucleophilic...

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