Chemistry: Spring Semester Lecture Notes



Organic and Biochemistry Name: __________________________AP Chemistry Lecture Outline0201654Video2503(3:10)020000Video2503(3:10)Introduction to Organic and Biochemistryorganic chemistry: biochemistry:-- Carbon is unique among the elements because:-- it can have up to four bonds per C atom -- -- 0139436Video2506(9:10)020000Video2506(9:10)Basic Definitionshydrocarbons: compounds containing only __ and __alkanes: hydrocarbons having only ________ bonds------ structural isomers: same molecular formula, different…alkenes: hydrocarbons having at least one _______ bondalkynes: hydrocarbons having at least one _______ bond402907520039600aromatic hydrocarbons: benzene and compounds w/abenzene-related structure-- –enes, –ynes, and aromatics are _______________4913473257127000-67046Video2509(9:33)020000Video2509(9:33)Finer-Point DefinitionsStraight-chain compounds have…56273897550500 Branched-chain compounds have… 560173010543400 Substituted compounds have… Branches and H-replacing atoms/groups are collectively called…Functional group: a characteristic pattern that makes up a portion of a larger m’cule-- -- importance: -- several examples of fgs:alcoholsketonescarboxylic acidsMany organic compounds are combinations of several categories.514817249101Br00Br4785217137196OBr00OBr4383309224562OOH 00OOH 741704180963Cl00Cl18038435080OH Cl00OH Cl06350Video2512(9:49)020000Video2512(9:49) Organic NomenclatureMemorize the prefixes that tell the # of C atoms in a chain.1 = 2 = 3 = 4 = 5 = 6 = 7 = 8 = 9 = 10 = 1871285209550003469460762000583986776200018531094127500Naming Straight-Chain Alkanes1. Find the longest continuous chain of C atoms. Choose the appropriate prefix.2. The name ends with –ane.EX.Provide the counterpart to the given.propane351957820574000Alkanes: modification for substituent hydrocarbon (HC) groups1. Number the “longest chain” carbons. Start with the end nearest a branch.2. Name and give the #ed location of each substituent. -- HC substituent groups use the prefixes based on the # of Cs, but end in –yl.3. List substituents in alphabetical order. EX. Provide each counterpart.4-ethyl-2-methylhexane11600971573120043132-96688Video2515(10:30)020000Video2515(10:30)Alkanes: modification for non-HC substituents1. The “longest chain” MUST contain the substituent.-- example substituents:–NO2–NH2 –F–Br–I2. Number the chain carbons, starting with the end nearest a substituent. -- A non-HC substituent takes precedence over an HC branch.3. Name and give the #ed location of each substituent.-- If necessary, choose #s so that their sum is as low as possible.EX.Provide each counterpart.3-bromo-2-chlorohexane2-methyl-1-nitrobutane3646170149225NH2NO200NH2NO2222250161290II00IIAlkanes: modification for cycloalkanes-- Use the cyclo- prefix before the “-ane” part.EX. Provide each counterpart.1-bromo-1-chloro-2-methylcyclopentane1117060655490041275-11083Video2518(9:55)020000Video2518(9:55)Alkenes and Alkynes1. The C-chain MUST include the multiple bond. Use –ene or –yne, as appropriate.2. Number so that you get to the multiple bond ASAP.-- The multiple bond takes precedence over branching or substituents.4665632233045003. Use di- or tri- right before –ene or –yne if you have two or three multiple bonds.EX. Provide each counterpart.237010766040001-butyne50159496350ClClCl00ClClCl7-fluoro-6-methyl-3-octyne4. For geometric isomers (different spatial arrangements of atoms), use cis- (same) 1836791241300ClClClClCH3CH2CH3CH2CH2CH3CH2CH300ClClClClCH3CH2CH3CH2CH2CH3CH2CH3 or trans- (opposite). Geometric isomerism is possible only with…EX. C=CC=C41275225545Video2521(7:25)020000Video2521(7:25) Benzene, Phenol, and TolueneThese are the “Big Three” aromatic compounds.For phenols and toluenes, the C to which the–OH or –CH3 is attached is carbon #1.benzene phenol tolueneEX. Provide each counterpart.bromobenzeneethylbenzene2-propylphenol45720012700CH3II00CH3II476186512700CH3NO2O2NNO200CH3NO2O2NNO22400300402590OHNH2H2N00OHNH2H2N4127574666Video2524(5:41)020000Video2524(5:41)ortho-meta-para-dichlorobenzeneFor this class, if a benzene ring is connected to an interior C atom in a hydrocarbon chain, it is called a phenyl (“FENN uhl”) group. It looks like THIS and has the formula…EX. Provide each counterpart.2-bromo-2-chloro-3-phenylpentane3-nitro-2,4-diphenylhexane378667110045BrBr00BrBr16827519050NH200NH24127598568Video2527(8:40)020000Video2527(8:40)AlcoholsAlcohols contain the hydroxyl group.-- low molar mass alcohols are soluble in…-- all alcohols have higher BPs than their parent alkanes Primary (1o) alcohols have one “R” group; secondary (2o) have two; tertiary (3o) have three.Naming Alcohols1. Without being redundant, specify the location of the OH group(s); the suffix is –ol.2. Use di- or tri- right before –ol if you have two or three OHs.EX. Provide each counterpart.1850366100593OH OH00OH OH1-propanol3-ethylphenol 3-ethylcyclohexanol449816020928HOHOOH00HOHOOH5-bromo-6-chloro-2-propyl-1-hexanol20510569215Video2530(10:18)00Video2530(10:18)Functional groups containing the carbonyl groupKetonesAldehydesEstersCarboxylic AcidsNames end in –one, w/the C in the carbonyl having the lowest possible number.Names end in –al, w/the C in the carbonyl being C #1.The C in the carbonyl is C #1. Whatever is attached to the–O– is named first, then the name ends in–oate. Names end in –oic acid, w/the C in the carbonyl being C #1.EX. Provide each counterpart.3-hexanone3-phenylbutanal3864515129540OFF00OFF82469771443OO 00OO 382963733128OO 00OO 86429512412OH00OH3-propylhexanoic acid4,4,4-trifluorobutanoic acidEthers(“EETH erz”)Amines(“uh MEENZ’)Amides(“uh MIDZ” or “AM idz”) 412754876Video2533(2:49)00Video2533(2:49) Other Functional Groups to Recognize41275262255Video2536(7:20)00Video2536(7:20)Organic ReactionsCombustion of hydrocarbons OR compounds w/only C, H, and O: products are…EX. Write the equation for the completecombustion of 2-methyl-2-pentene.Write the equation for the completecombustion of ethylbutanoate.substitution: an H atom is removed and “something else” is put in its place-- In halogenation, a ___________ atom replaces an H.EX. Write an equation for the reactionbetween ethane and chlorine.If more chlorine is provided, the reaction will produce...AND SO ON.Substitution occurs with aromatic compounds, too.685800137795+ Br2catalyst00+ Br2catalyst685800274955catalyst+CH3CH2Cl00catalyst+CH3CH2Cl41275195951Video2539(4:53)00Video2539(4:53)4004490252095HHHH C=C+H2OH2SO400HHHH C=C+H2OH2SO4addition: a multiple bond is broken and two “things” are inserted86048511430HHHH C=C+ Br200HHHH C=C+ Br23871140254000 H–C–C–C–C–HH+Cl2HHH00 H–C–C–C–C–HH+Cl2HHH-16510695860086048557150HHHH C=C+HBr00HHHH C=C+HBrA specific addition rxn is hydrogenation, in which ___ is added across a multiple C-C bond.-- requires a catalyst (usually a finely-divided _________) to rupture the multiple bond135219019685HHHH C=C+H2catalyst00HHHH C=C+H2catalystAnother addition reaction is polymerization. 905510169545HHHH C=C00HHHH C=C3191510160020HHHH C=C00HHHH C=C204877445720HHHH C=C00HHHH C=C429667419240500176659450129“lots” of ethylene00“lots” of ethylene41275170144Video2542(6:26)00Video2542(6:26)condensation (or elimination, or dehydration): _______ is a product-- One reactant provides an ___, the other provides an ___.6858010160H2SO4+ HNO300H2SO4+ HNO354679738318500 CH3CH2OH + CH3OH19818025844500-- Condensation reactions polymerize amino acids into…-- Amides can be formed in condensation rxns between carboxylic acids and amines.EX.Write the equation for the reaction between butanoic acid and ammonia.47359021102610041275172780Video2545(5:33)00Video2545(5:33)Esterification is a condensation reaction that occurs specifically between a carboxylic acid and an alcohol.57829817894400EX.Write the equation for the reaction between butanoic acid and 1-butanol. EX.Write the equation for the reaction between 3-phenyl-2-propenoic acid and ethanol.5468512733300 ................
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