Exam 3 study guide
Exam 3 study guide Chem 372
Popular in Organic Chemistry
Popular in Chemistry
This 4 page Study Guide was uploaded by Rachel Taylor on Sunday March 20, 2016. The Study Guide belongs to Chem 372 at Eastern Michigan University taught by Dr. Friebe in Winter 2016. Since its upload, it has received 39 views. For similar materials see Organic Chemistry in Chemistry at Eastern Michigan University.
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Date Created: 03/20/16
Exam 3 study guide: Chapters 19, 20, 25 The ability to name and synthesize carboxylic acid and its derivative through oxidation and reduction reactions is going to be key to this exam. You do not need to memorize each mechanism as you should be able to derive it by knowing how each reagent works. Also knowing how to use organometallic compounds and basic properties of Aldehydes and ketones will also be on the exam. Common reducing agents LiAlH , H 4 Pd2C, NaBH + CH OH4 DIBA3-H, and LiAlH[OC(CH )3 3 3 o LiAlH i4 a very strong reducing agent o NaBH , D4BAL-H, and LiAlH[OC(CH ) ] ar3 3 3e selective o Pd-C reduces C=C first then C=O Common oxidizing agents CrO , Na3r O , 2 7r O 2an2 7gO in NH O2 (sele4tive). o Metal-carbon (RLi, RMgX, R CuLi) bonds react to form carbon-carbon bonds 2 o Organocopper reagents only selectively react with polar bonds (Acid Chlorides, lithium-carbon bonds) Protect OH groups with TBDMS and remove with tetrabutyammonium fluoride. 1. Draw 7-ethyl-5-isopropyl-3-methyldidecanoic acid; Lithium pentanoate; 2,3- dimethylcyclopentanecarboxylic acid. 2. Draw the result of butanoic acid reacting with LiAlH ; NaB4 + CH O4; AgO3H O 2 3. Describe the structure of Amino Acids at low PH, High PH, and isoelectric point. 4. Between aldehydes and ketones, which is more reactive and why? 5. Question given in class: Synthesize 1-phenyl-2-butanol using only the reagents listed above, H 2, CO ,2Benzene, propene, and methanol. Answers 1. 2. No Reaction 3. At low PH (or high concentration of protons), Amino Acids have a net positive charge because the NH ha2 a lone pair and acts as a base turning into NH . At h3gh PH (low concentration of protons), Amino acids have a negative charge because hydroxide ions in the solution take the proton off of the carboxylic acid. The isoelectric form is when the amino acid is primarily neutral. 4. Aldehydes are more reactive because it only has one bulky R group rather than two and therefore the single R group does not stabilize the partial positive charge on the carbon. The electronegative oxygen has a partial negative charge and the carbon it is bonded to has a partial positive charge, therefore two R groups in a ketone would stabilize the partial positive charge making it more stable than an aldehyde.
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