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NCSU CH 220 - Review Session

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CH 220 1st EditionExam # 3 Study Guide Chapter 5- Recognize aromatic compounds and be able to name them using current IUPAC nomenclature. o Monosubstituents – put name of substituent in front of Benzeneo Common names (make sure these are on the worksheet – can use in exam) These common names can be used as parent names in larger compounds: 2-bromotoluene- Understand and be able to predict the products of the following Electrophilic Aromatic Substitution reactions:The halogen can be Br2 or Cl2Needs a catalyst – FeBr3 or FeCl3Needs a catalyst – H2SO4Needs heatResults in benzenesulfonic acid and H2OUses an alkyl group attached to a Cl (has to be a Cl, no other halogen)The alkyl group could be any alkyl groupRequires a catalyst – AlCl3 (Friedel Craft Catalyst)Requires heatIt allows you to make a bond between two carbons, which has high commercial valueCarbonyl group reacts with benzene ring using AlCl3 (Friedel Craft Catalyst)Requires heat of at least 80CThe carbonyl group is very reactive and so ‘opens the door’ for the reaction to happenKnown as functionalization – attaching a functional group in order to extendThe carbonyl group can be attached to any alkyl group - small or large- Understand and be able to explain which groups are ortho/para directors and which groups are meta directorso When asked to name IUPAC, use #s for substituents, for common use o-, m-, p-- Be able to synthesize simple benzene compounds, including substituted benzoic acid derivativesChapter 6- Be able to explain the concept of chirality and recognize chiral centers (asymmetriccarbons, stereocenters) in a given compound.- Be able to recognize and differentiate enantiomers (stereoisomers that have the sameformula, the same connectivity, but different orientation in space, R/S).Uses priority system, like EZ1. Rank 4 different substituents by atomic number and build with model kit2. Hold the lowest priority substituent facing away from you and look at the remaining 3 groups on a plane3. If the priorities 1,2,3 are clockwise then it is designated R (right)4. If the priorities 1,2,3 are counter-clockwise then it is designated S (left)5. If a decision cannot be reached by ranking the first atoms in the substituents, look at the second, third or fourth until there is a difference- Be able to use the sequence rules of Cahn, Ingold, and Prelog to assign theconfiguration of a given stereocenter (R/S system).Chapter 7- Be able to recognize alkyl halides (same as haloalkanes) and name them using currentIUPAC nomenclature.o Triple bond needs to be in the parent chaino Number from end nearest any substituent (halogen or alkyl – neither have priority)oo If two halides or alkyls are equally distant from the ends of the chain, work alphabeticallyoo i.e. 2-bromo-5-methylhexane- Be able to recognize a substrate, nucleophile, and leaving group.o O- is the nucleophile, Cl+ is the leaving group and the methyl group is thesubtrate- Understand and be able to explain (in detail) the mechanism of bimolecularnucleophilic substitution (SN2), unimolecular nucleophilic substitution (SN1),unimolecular elimination (E1) and bimolecular elimination (E2).Reaction Substrates Solvents Nucleophile StereochemistrySn2 Methyl>1>2(never 3)Acetone or DMSO NaCl, NaBr, NaI, NaCN, KCl, KBr, KI, KCNR -> SS -> RElimination reactions E2o Elimination reactions happen when, instead of attacking the Carbon, the nucleophile attacks a hydrogen en route to the Carbono This happens when the nucleophile is a strong base such as NaOH and KOHo By making the nucleophile bigger, meaning that it would be harder to reach the carbon and make it more likely to attack the hydrogeno Using Sodium Methoxide instead of NaOH, there would be a much greater chance of thereaction being an Elimination Reaction (E2) o Produces an alkeneo The nucleophile attacks a hydrogen on the Carbon neighbor of the Carbon with the leaving groupReaction Substrates Solvents Nucleophile StereochemistrySn1 3 > 2never methyl or 1H2OAlcoholHCl, HBr, HI, HCN R -> R&SS -> S&RElimination reactions: E1o OH group is not a good leaving group, so must be protonated, creating water (a good leaving group)o The reaction results in a major and minor product if there is not a strong anionIf there is a strong anion, it will only result in one product- Given a substrate, solvent, leaving group, and nucleophile, be able to predict the majorproduct of a reaction and its correct stereochemistry.- Given a set of conditions, predict the outcome of a reaction in which elimination andsubstitution mechanisms are in competition. Chapter 8- Recognize the alcohol as a functional group and be able to name alcohols using current IUPACnomenclature. Primary, Secondary & Tertiary Alcoholso 1 alcohol is an alcohol attached to a 1 Carbono 2 alcohol is an alcohol attached to a 2 Carbono 3 alcohol is an alcohol attached to a 3 CarbonNaming alcoholso Select longest parent chain (including OH)o Number – OH group has lowest #o Substituents are then numberedo Parent group has –ol suffix- Be able to explain how the structure of alcohols correlates with their physical properties. Properties of alcohols and phenolso They bridge the gap between animals and hydrocarbons/inorganic and organic moleculeso Hydrocarbons are hydrophobico Use hydrogen bonds (don’t draw a line for a hydrogen bond, just use dashes – not a solidbond, but a strong association) Cannot form a solid bond because electrons are otherwise engaged- Understand and be able to explain how to synthesize alcohols by using a hydration reaction (from Chapter 4) or nucleophilic substitution (from Chapter 7), or areduction reaction with sodium borohydride (from Chapter


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