CHEM 2760 Test 2 Study Guide
CHEM 2760 Test 2 Study Guide 2760
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This 8 page Study Guide was uploaded by Tyler Ebeling on Wednesday October 12, 2016. The Study Guide belongs to 2760 at East Carolina University taught by Shouquan Huo in Fall 2016. Since its upload, it has received 85 views. For similar materials see Organic Chemistry 2 in Organic Chemistry at East Carolina University.
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Date Created: 10/12/16
CHEM 2760 Test 2 Study Guide 10/12/16 Professor: Shouquan Huo Chapter 12: Organometallic Compounds Organomagnesium compounds (Grignard reagents): This is a simple reaction in which an alkyl halide is added to magnesium shavings with ether as a solvent (usually diethyl ether or THF). It’s easy to remember because magnesium is always the metal used, and it always inserts itself in between the halide and the alkyl group, as seen below. Transmetallation: Transmetallation is basically when one metal is replaced by another metal in a metal halide. However, this only occurs when the metal that is attached to the carbon in the metal halide is less electronegative than the metal that is to be added. Organocuprates (Gilman Reagents): Not to be confused with “Grignard reagents,” organocuprates are compounds that are used in coupling reactions. They always appear in the general format of2R CuLi. As seen below, when the organocuprate reacts with an alkyl halide, the alkyl group attached to the organocuprate (CH CH ) replaces 3 2 the halogen (Cl) group. *NOTE* organocuprates cannot react with tertiary alkyl halides. They can, however, react with vinylic halides and aryl halides. Suzuki Reaction: The Suzuki reaction combines the R group of a vinyl or aryl halide with the R group of a compound with boron in it. The reaction takes place in a basic solution with PdL 2 present. It is important to note that a Suzuki reaction will always have a trans conﬁguration. Heck Reaction: The Heck reaction has similarities to the Suzuki reaction with the biggest difference being that instead of involving an organoboron compound, the Heck reaction involves an alkene. It uses the same PdL catalyst2 and the base is often (CH 3H ) 2 3When the reactant is a vinyl halide, the conﬁguration of its double bond is retained. ***You don’t need to know section 12.5 for this test*** Chapter 13: Radicals • Reaction of Alkanes Halogenation reaction: A halogenation reaction is where an alkane reacts with chlorine or bromine to form an alkyl chloride. They only occur at high temperatures or in the presence of light. This reaction, like pretty much all reactions in chapter 13 involves 3 steps: the initiation step, the propagation step, and the termination step. Dr. Huo said that we only need to know the initiation and the propagation step. I would learn the termination step too though, because he said that we could possibly get extra credit for knowing it. Stability of radicals: The stability of radicals is in the same order as the stability of carbocations. This is important to know because the stability of intermediates within a reaction helps determine what the major product will be. It’s important to note that the benzyl radical and the allyl radical are more stable than a tertiary radical. This is because of electron delocalization that occurs between resonance structures. Relative rates of alkyl radical formation for chlorine: Tertiary (5.0) > Secondary (3.8) > Primary (1.0) The numbers above mean that a tertiary radical is 5 times easier to form than a primary radical. A secondary radical is 3.8 times easier to form than a primary. *Note* these numbers only apply to room temperature. Relative rates of alkyl radical formation for bromine: Tertiary (1600) > Secondary (82) > Primary (1) Since tertiary and secondary radical formation is so much easier than primary radical formation, bromine can be used when a speciﬁc product is desired, as it will form much higher percentages of that product than chlorine would in the same reaction. Reactivity-selectivity principle: This principle states that the the more reactive a species is, the less selective it will be. This makes sense if you think about it. If a species is super reactive, it doesn’t care what it reacts with. If it ﬁnds a way to react, it’s gonna do it. Contrarily, if a species isn’t very reactive, it needs ideal conditions to react. This means that it will be picky (selective) about what it reacts with. ***DON’T NEED TO KNOW SECTION 13.6*** The peroxide effect: This is something that is only observed with bromine. Under normal conditions, when HBr reacts with an alkene, the hydrogen adds itself to the carbon with the most hydrogens, and the bromine adds itself to the carbon with the least amount of hydrogens. However, when a peroxide (ROOR) is added, the opposite happens. The hydrogen goes to the sp carbon with the least amount of hydrogens and the bromine goes to the carbon with the most amount of hydrogens. ***I highly recommend looking over section 13.10. Dr. Huo said that there will be synthesis questions on the test, and section 13.10 is good practice. *Don’t need to know section 13.11 or 13.12* List of solvents and what they do: NBS: Used to brominate to an allylic carbon (the carbon next to the double bond but not part of it) Peroxide: Causes anti-Markovnikov addition of Bromine. HI plus ∆ (heat): Turns an ether into a primary alcohol >> NaOCl / CH COO3 0ºC: Turns a primary alcohol into an aldehyde. Br 2r Cl : 2hese are the only molecules that an alkane (single bonds only) can undergo a reaction with. High concentration tert-BuO / tert-BuOH ∆: Not to be confused with high concentration of CH O/3H OH, 3ert-BuOH is an E2 reaction that forms a double bond where the Br was. BuOH is a strong base, so it’s used when an elimination reaction is desired over a substitution reaction. CH O-3CH OH i3 used when a substitution reaction is either unlikely or impossible. Chapter 16: Reactions of Carboxylic Acids/Carboxylic Acid Derivatives Names and structures of compounds that we need to know for the test: Propionic Acid Ethyl Acetate Acetate Acetyl Chloride Benzoic Acid Benzenecarboxamide Urea Sys. name: ethanoic anhydride Benzonitrile Common: acetic anhydride ***Don’t need to know the common names of lactones*** ***Don’t need to know section 16.4, 16.13, or 16.23*** Reactions of acyl chlorides: The reaction of an acyl chloride with an alcohol results in a hydrogen from the alcohol joining with the Cl, and the rest of the alcohol taking the place of the Cl. Hydrolysis of an Ester: The ester reacts with water to form a carboxylic acid and an alcohol. This reaction is slow, so a catalyst is always used (the catalyst is an acid). Transesteriﬁcation reaction: This reaction involves an ester reacting with an alcohol to form a new ester and alcohol. It is also always catalyzed (most often by an acid). Fischer Esteriﬁcation: This reaction is almost the opposite of the hydrolysis of an ester. The starting materials are a carboxylic acid and an alcohol. When those two are treated in the presence of an acid catalyst, an ester is formed. Reaction of amides: Amides do not undergo reactions with water and alcohol under acidic conditions. However, they will react with water and alcohol if the reaction is heated in the presence of an acid. Reactions with water form carboxylic acids, and reactions with alcohols form esters.
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