Popular in Essentials of Organic Chemistry
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This 50 page Bundle was uploaded by Nepenthes_Fan on Wednesday August 19, 2015. The Bundle belongs to CHEM 330 at Towson University taught by Mr. Macks in Spring 2015. Since its upload, it has received 44 views. For similar materials see Essentials of Organic Chemistry in Chemistry at Towson University.
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Date Created: 08/19/15
M Mar I believe that scientific knowledge has fractal properties that no matter how much we learn Whatever is left however small it may seem is just as infinitely complex as the whole was to Start with That l think is the secret of the Universe lsaac Asimov Will cover highlights but will not go into detail rather speaking to effects More things to know iRapid talking Above gen chem but clearly underpins biochem and pchem Much of what was learned is selfconsistent but not coherent in the larger scheme Donald J Cram quote Not just collections of individual facts not just formulae Structure can be as imp as formula and more imp than the actual elements at a 1 We learn nomenclature in order to communicate about nomenclature In org chemistry the naming corresponds DlRECTLY to the chemical formulae and structure Acid is even a group The DH and double bonded 0 makes up the acid functional group N 390 RG Cl I EM IS U N AM Bl G U 390 U V 1 r Facts are not science as the dictionary is not literature lVIartin H Fischer Will need to apply facts and make coherent understanding of all facts presented What is Does it Mean to be different In a chemically relevant way Chemicals do not have inherent front and back 39C4H l 00 We use models of ball and stick to show the Threedimensionality of the molecules Can be rotated or tilted a 2V 0 a g I Not always useful to know the explicit formula sometimes more imp to know the shape a M H0 4 mm Haw 63m the same facts but they are diff representations 74quot of lines and placement changes the above have double lines and those are chemically diff First two are butyl alcohol second two are crotal alcohol but are NOT the same because of the Curve after the double bond 3 classes of problems determination of significant fact matching of facts with theory and Articlation of theory exhaust l think the literature of normal science both empircal and theoreticaL Both are hormones but very diff functions Another examples are pseudoephedrine vs methamphetamine Quite simple to turn the former into the latter just by removinng the OH Phenylephrine is also similar same class of molecules bt has extra and is missing a group l Ias similar effects but can39t be made into methamphetamine Week 63m x2444 Wm M y 5 War t Ask for questions or examples or clari cation Check for all announcments on blackboard Course info section on blackboard is the syllabus no paper syllabus lab begins in same room as lecture then moves to the lab room 589 7th is current ed of the textbook Note to self make jipegs of the relavent diagrams in the book to make it easierfaster notes in lecture The letter grade is 65 lecture and 35 lab 4 exams and the final Can drop lowest test grade if more than 3 exams Final counts for 2 in class exam grades Org Chem 2r gr 5 My notes 23 Cycloalkanes l Saturated cyclic hydrocarbons have the general formula an or Man J g a A D Cyclopropame Cyclobutane Cyclopentane Cyclohexane Naming Step li Find the parent Count of carbon atoms in ring and largest substituent chain a lf ring gt substituent name as an alkylsubstituted cycloalkane I l Step Two Number the substituents and write the name lf more than one substituent begin at the one with alphabetical priority and number in such a way that all substituents have the lowest possible 0 a V l CV3 K L Y z 39 39 A N07 5 Problem 23l 8 Name the following 1 nu LL A C a 28 ZiaTrans lsomerism in Cycloalkanes Class Notes Geometry sometimes matters Represents the idea that pieces must t together to work but does not show how the molecules actually look iThe ligand has to if its too big will just wash past it too small won39t have the correct interactions EDNA forms the same geometryshape every time Proteomicsa how do proteins quotknowquot how to fold H g Ct W What is ditiisjust where each thing points 1 quot f f Arbitrary K H 39 If x NEH r g V V Only 3 choices iin the plane of the drawing line icorning forward out of the plane of the drawing wedge going away behind the plane of the drawing dotted or faded line or wedge t t H M 4m Am M Ma V mo MIOW M M a loc Daugu QW mob 80mm Q0 4391 i Egg They have a differeth Relative Geometry Where are the two halogens relative to each other Are they 39CIS near or TRANS tar relative to each other CREEW i ew7 CZC CSC H Hi 39 H w I H BF C 75 We know we are talking about the carbons l and 4 because we do not talk about ll39y drogens we just refer to the quotnot H39s O aw am 0 amp Us and trans only part of the name when you have nonll atoms changing Places relative to one another v M DNA can twist into the helix b c even though there are double bonds between the bases the backbone is all single bonds A I I Always want the substituent to be numbered as low as possible Additionally must start with the alphabetically lrst substituenti Org Chem 22615 Stereochemistry Everything about DNA is curved so if anything wants to connect to it it must have the correct curve the same handedness or it will not t The idea of clockwise and counter clockwise matters This quot39handedness property is called Chirality They are mirror images but not THE SAME More subtlethan cis or trans AKA Absolute Stereochemistry Any times an atom is tetrahedral and is pointed to a speci c thing it can have an absolute stereochemistry 2 EH 7 is 39 9W 40ft cid Yeur hands are Enantiecmers of each other Tel be ehantiemers the Chemicals must be the same isomers as each other H W a 0L u 0quot M44 ux W sesame ampW ECgZ ng estfomwe Can you put these in alphabetical order 0f zume because you know that A comes before B and so on PPLE BUZZ geey Z A Know that baby comes before buzz because even though they have the same rst letter they have different second letters Only look further down the word if you neecl to break the tie between the rst letters Can use the same pattern recognition to determine the stereocenter in a molecule MF 3 Steps Step 0 Recognize its tetralheolral Step 1 Write atomic number Step 2 Putin numerical order Step 3 Make sure they are in order as drawn Even if the molecule is complex it still lhas only 2 stereoclhermiatry only two options tor nandedness 1 th 7 quot 02 A H 5M 02 W i g rm FZJ39 Org Chem 1 2939 Ch 1 Preclass notes Structure and Bonding Acids and Eases Organic Chemistry Only dlistinguishing characteristic of organic molecules is that they allll contain carbon Of presently known 37mil compounds 99 contain carbon quot V 11 Atomic Structure Atom Dense r charged nucleus Suliatomic particles neutrons 0 and protons gExtremely small in o M Electrons have nearly no mass andl encircle the nucleus at M Ma aDiameter of atom v rem H or Angstrom E s 1 usually used 11 100pmf015 in Class Notes Language of org clhem The formula is a good model for determining charge weight etc Maillot lan 4 Ciao Self consistent in that in water this is its nature in reality no such molecule as NaCl Why NaCl does not exist as an NaCl unit lout rather lots of Na and Cla 1 Nair Clquot Mr lElFan l Mam Ms So another reason we tallk alboutNaCl lbeinga unit is lbc it is a 1 11 pairing of neutrality None of the atoms are neutral but they do lbalance each other out The atomic clusture of NaCl is neutral One of the reasons that NaCl sticllts together is that oipip charges attract lonic attraction Cilr 16ish gmol Hard to measure hc gas not solid 14 32H ratio Org molecules have structure in all states of matter Quasar en sm r mo may a 7 No matter what you do methane always retains the 3912 i i I unit Units retain intact nature but change association From otherunitslntermoleculardistance rather 7 Thanintramoleculardistance 739 I I So Drgo chem is more accurate in its 1k Estimation of mass since there are 100 i 39 Actual physical units rather than the W Ionic associations bt Na and Cl A quot 0 x WWl Chlorine gas was used to create a toxic gas diatomic gas We Diatomic molecules have a discrete physical pairing so 02 each Cl is exactly neutraL Not neutral bc they balance out but rather bc each atoms is exactly El and 02ifl Most orgo molecules are atomically zero bc they are Zero in each part at each atom The column an element is in on the periodic table is just one hueristic one way it might be ExilIydrogen can be t or t Bic every atom is stable the methane molecule is very stable without charge attraction what holds molecules together In the case of methane El r Cit faint lls is nearly impossible to exist and Jill is impossible to exist Why What makes l moe stable Look at Ethane The Hydrogen on the first C are speci cally on THAT carbon and the other three are specifically on the other Carbon H a I l I H 144 A Ij ow VVIL XI The chemical formula is ambiguous for Almost everything orgo Both Ethanol above and the other molecule Below are Us but they are NOT the same H So even though the pieces are the same the structures are very different They are str quotctura isomers i Or constitutional isomers So nomenclature in orgo is incredibly important The name talks about the structure not just the39i in the bag Each atom is spaced apart from the other H I By the electrons Sticks are better because it shows how the 39 Electrons are shared bt specific 39 39 Atoms 39 39 So we can repartition the shared ai Essentially saying that one electron is the Carbon39s and one is the hydrogens Ownership of the electrons in a covalent Bond n Bc atomic weight is t2 carbon we can deduce that most of the time carbon has 6 neutrons too But there is some carbon like Hf that has more or less neutrons and are less stable We don39t need to care much about the actual charge bc of the protons in the nucleus just the valence electrons the math will be quite simple We work mostly with the formal charge resulting from the summation of the valence electrons as denoted by the column numbers go the formal charge for each atom and its valence electrons is zeroneutral illii L 1 I lug u as i i a P 1 This is why we incorrectly assign speci c electrons to specific atoms in order to talk about the molecules covalent bonds Water tends to stay discrete units bc Then its a formal charge of U which is Stable 933 574 I a Atomic Structure Electron Contigs Groundstate e conhg is the lowest Energy arrangement Worlked ex quotIII Give the groundasta Electron conhg of Nitrogen N has 7 valence e so it would he 39 l i 1 Q3 ls l52L 52 99 Went over 1 L4 L5 in class with diagrarns of electron sharing 139 Polar Covalent Bonds Electronegativity Electronegativity tends to increase tron1 lgtR and bottomagttop on periodic talsle 39 H 39 239 v M 39 transition Hermie u Inf 7 b The e will be drawn toward the more electronegative atom in the bonding pair 110 Acids and Bases 39l he Bronstedlowry Definition Acid substance that donates a hydrogen ion H 9 3 1 i1 1 Organic acids and bases Org acids clharacterized by presence of positively polarized lhydrogen atom and 2 main lkinds Acids suclh as methanol and acetic acid tlhatcontain an H lbound to an electronegative D 0H Acids suclh as Letone that contain a H bound to a C next to a 30 gt CCH Carpoxylic Acids contain tlre Cfl2H Involved in metabolic patlhwaysw L158 C is l Organic Bases clharacterized by presence of an atom with a lone pair of e that can bond to H Nitrogen containing compounds lilke metlhylamine most common but 0 containing compounds can act as lbases wlhen reacting w a strong enough acid Som lilke Me tlhanol and Acetone act as acids when they donate a proton but act as lbases wlhen ltlhE39ll39 0 atom accepts a proton I O Jquot 9 ll Amino Acids so named lb c they are both amines Wt and carpoxylic acids Cad exist primarily as zwitterion lbc tlhey lhave lbotlh acidic and basic sites Within the same molecule and therefore undergo internal acidebase reaction 112 Acids and Bases Lewis Definition Acid substance that accepts an electron pair Base substance that donates an electron pair Most O and N containing orgo compounds can act as Lewis bases bc they have lone pairs of e2 Ch 2 Alhanes The Nature of Organic Compounds Relatively unreactive 21 Functional Groups a group of atoms within a molecule that has a characteristic chemical behavior Th e ohemis try of every orgo molecule regardless of size and complexity is determined by the functional groups it con tain st Functional groups w Multiple Bonds EAromatic Compounds Ahenes 8 lC Al lltyn es Arenes Functional Groups with Carbonn sineg bonded to an electronegative atom Alkyl l lalid Haloalkane Alcolhol Etlher Plhosplhate If I rr 391 Disulr de Functional Groups w a Carbon0xygen double bond Carbonyl Groups Aldelhyde O Ketone Carboxylic acid Ester A a I 395 1 xquot H CC CC a 39 I 3 C12 a 39 39 KM 39 Thioestg Amide Acid Clhloride 2i2 Allkanes and Allkyl Groups lsomers Alkanes are often described as saturated hydrocarbons bc they contain only carbon and bydrogen and saturated because tl39iey only bave CEO and Call single bonds and thus contain the max of lhydrogens per carbon Have general formula of Cu our wlhere n is any integer Alipba tic bc animal fats contain long carbon cbains similar to allltanes For the tirst 3i combos only one structure possible all can only be me tlhane W can only be etbane Calla J9 Cll l l can only be propane Q Any larger and multiple lkinds of molecules can form f Crux can be either Butane Clito 3 3quotquot or lsobutane drip tilt 3942 Compounds lilke Butane with Us connected in a row are called straightgchain alkanes or normal alkanes and compounds with branclhes C clhains lilke lsobutane care called branched chain alkanes ca ii ritten 2methyipropane to denote wh ere it bran ches Allltyl groups are allltanes where a hydrogen atom has been removed ERemoving a H from methane LL generates a methyl group 5 Removing a H from ethane Cutting generates an ethyl group Cilzws Removal of a hydrogen atom from the end carbon of any reallltane gives the corresponding reallltyl group H atoms can also he removed from an internall carhon generating hranches allltyl groups Propane Prop l Isopropyl D O 0 r I o o o o 6 0 0 b We to are Myer One further note The pre xes sec for secondary and tert for tertiary refer to the of other carbon atomms attached to the branching carbon atom Primary 1 w Secondary JG Tertiag 3 9 Quaternary ftquot 23 Naming BranchedaChain Allkanes REFx Jitterr atomr Where Carbans Whareisthe What isthe Primary Functional Group What Primary Func onal Group Org Chem 2 24 II 5 1 EFI UOrO bUit T ene Permentantly in this shape bcause DOUBLE BONDS DO NOT TWiIST OB CHANGE SHAPE Oan39t become cis because there is an H in the way A iln a double bond the two 3 are permenantly fixed in a planar geometry relative to each other One of the reasons DNA can bend And twist around is that it has SiINGLE BONDS in it39s backbone u Rings have the same properties of a sheet of paper They have two sides and are flat On every corner carbon there is something moving away relative to the flat ring and another coming toward you relative to the rings One of the reasons DNA can form the elongated structure is because the oxygens coming off it are going in OPPOSlTE directions relative to the flat polygon on opposite faces of the ring compared to each other The chain forms an ordered stacking front to back stacking in the third dimension to create a nice double helix FQFUUr w lrrlportant takeaway here is that you can39t just switch the two groups on the corner of a ring You cannot arbitrarily switch two groups on any one atom The atoms can39t pass thru each other directionality is permenant With reference to the hyacinth lab this is why the halogenation reaction and breaking of the double bond will happen in different reactions and have different results based on where the Br39s abachi ks s g 1n 3 w l A W M ID39na can form elongated structure because the pieces of the backbone are TRANS to each other Opp eye Q4 game Orgo 42115 V Iquot V a n A r Wk Q Hd GENT H157 j Liv39M l md rt A f V Z iff luw L MH Fr Hawaii a vmwd gih d f if CE RMgX39 quot13 WLA D 954 4 W T4 4 W 41 11 i397 rlwi u 65 mm f u39f m sllr1 Jr mm H w E E 39 ft f m 0W5 m W h mg I a HI x v Lime WWW u 319 39 I kquJCfI rz V 393 Hr chlwd LI ILIF jh O L f 3 airlute 0m 4mg pwr 39 I h JEEW EEL Cuff orlicmkay 39JC wvbc 39 1 me t kh A V CIAbow m 5 Ho M3 Z SW61 j I 5 439 gal FriCm 399 H a 39 39 H quot 7 quot i 1 aWMfmnTta 5mm 653thle CM ME game s qdwmgg quot 34 with L ER W1 CE 4 5qu 3 mm g i i quot I 1 Quima ra H e 7 1quot HM 3045am draw ns MEG 51 H H ma de m O CFG V I 0 I k quot 1 cu CAEJUIHL JK Arm DIEMW HM74 7 red i gt I I I 9 7 lmah wwrx Fad am Warri w h 4 quot rm 3 jwa39m xmpdwnw Sipdi fin quotm v 1 r t 30135 4 c39lm ql CWWQL WE mfp wi DM iguana Jawj a Mama mmmm I 01 L x L V 1ka 39 1mm W o uaut tkj J39w 30 t 39 VC V 39 7 D f m tjh W 392 mi 1 m orquot mlhm A a gag 7 391 i5 51quot CHEWth an arm Giana d7 T EQAEF Ca I 2 I W 0x WUE I M3 anci39tdm 3m 61M 3qu 166 Fquot Hui 0 xx 9951Aer whamknt rwa W f a K a 0 KJKH 7 mama Wm 39 13 960 8 m 09mm 805 Uomm 853 f rays in a F is g 9 1qu f O Eto ngrxg a pr V 26 Du 3 I 30 r o n n 350 my men A E Z in E 2 o p 9L 8 Z O w w W EL 111 11 i 11 ll 39 II39I II II 11 1 all Ill 50 a AoEfde REE MTWEJ J In x Q0 1 x 0J lt o g 0 k W4 OVvwU 11 R I a If 1k 6 m gt12 L 2 I A b L AI 00 all OD f REL 36133 g o Fa 2 g lt3 EtcTE P 3 emacxx we 3x g 49 a 0 mgpr bv 22 O r Er Quickies 231 Z E of E 5 Edit lt Qamu Q 35 g aft 5st raw 7 bahpx 3031 a mu 5 F r vs 313 0ng ED an 2 3 IW0 00 bOmErS rh tp T no g 5 060 naming m 3 0 03 xmi m K xth This reaction kinda jlust lets the electrons go in the direction they are all being slightly pulled anyway by the dipole Carbonyls are much stronger as a bond than alkenes 30 is stronger than Cit But because not symmetric electronically they are easier to cause change with incoming Susceptible to nucleophilic attack APPLlCATlON OF THOSE 2 FACTS EXPLAIN REACTl39ONS FOR THE REST 39OF SEMESTER Remember when a Nu attacks a trig planar atom it can attack from either face of the planar molecule LL91 PosslBKL NU39CLEIOPHiILiIIC iINiITIATED ME39CHANiISTIC STEP similar to 8112 that way But similar to Snt in their actual geometry and the stereochemical results 9M m m a 39 3 h CM hankfx quotr 4 5 I39mquot HO 5AM cw Le Org Need to be i Simple h CHC Concise t Always number in a way So that the tor the sub 39 Stituent is at the lower iAlways HQ with the lowest Numb being where the substituent is So whilethere are j l 6 carbons one otthem ll 39 Cf Ca C F C lls branching otttheretore This is pentane not hexane I y I Additionally just saying methyl Pentane is not enough also need to say H H What number the extra carbon is branching from F loam M This only needs the name no a since there is only l carbon Rules for naming lVlust be organized lVlust be concise lVlust have the lowest position possible Alohabetioal order llunnerical order quot 22difluoroetl39laPIE H 239liliflueree1thane New lelt39s simplify by gelling ricl eflhe l I39s we can and the carbons i ll 39 Same as Ol quot l same as lf ne elemenlt symbol it means earben H 0 l H H I M be m Fez V o a l i Hf l l all g laws wok w Li39s a W5 Ea l5 H nelte lthis enly werks iflth C has l lquots if the C has a lfermal charge 0f 0 then l lave its have 4 bonds wf lNelthing else named must Be hydregens Cl t t U 7ng I l l 0mg 3 4 g Joell frivolch frivolch ud a invalung 3 I lef39 it ax J The quotTe molecule does not have a satis ecl octet so is E instable but has formal charge stability The Be molecule is FC instable AlNlD octet instable The quotBequot is FE instable and octet stable Electronic Stability We39d Lula hm MW nights m M at Mt Wm itquot WM s mlquot Urge Chem 331 1 5 Putting pieces together i 39 39 if Mquot xn MW 39 T quot7 quot u ewes 393 W Muff 7quotquot W 13 u39mkxmlmnul rm 9 amt 1 obw w an I will 39H nc H 9 M e quot q H I v gt 9 39 m H 39 39 3 4 r1 Paocego 1 42 0 V Ham wurgk oxmg gt0 5 I E FUOMWEDF Pvt Ehgx er 43mm g y 19 WEE 4f 41 Eli 995mm 59 TM 30 3322 am 0 m amazes VA in rant i A g I i L A g EF 00 The EVE lair t W l Rs 6 QB CF W g Q 4 V 50N WP Err S39b gm39mMM lis i
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