Organic Chemistry 1: Study Guide Test 1
Organic Chemistry 1: Study Guide Test 1 CH320M
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This 8 page Study Guide was uploaded by Heidi Notetaker on Thursday September 24, 2015. The Study Guide belongs to CH320M at University of Texas at Austin taught by Dr. Shabbir in Fall 2015. Since its upload, it has received 96 views. For similar materials see Organic Chemistry 1 in Chemistry at University of Texas at Austin.
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Date Created: 09/24/15
Heidi Shay Study Soup Fall 2015 Organic Chemistry 1 Test 1 Study Guide Electron Con guration and Symbols 7 Octet Rule e Electron Formal Charge y 39 quot t 7 N 1 7 H I y 1 Covalent Bonds E E Emmegaumy 7 Electronegativity 7 H i r Qua mm Meghamcs MO Molecular orbital Resonance 7 w r Functional Groups VB 7 7 valence bond Naming Alkanes and Cycloalkanes a Single valence electron Straw and Sammy V A 7 V Wedge showsan atom coming outin front Drawmg Chair Conformations of thespilane surface 7 r 5 Dash shows an atom going intobehind the 3 7 plane surface 7 Line shows an atom on the plane surface Organic chemistry the study of the compounds of carbon includes hydrogen nitrogen oxygen nitrogen 1 Electronic Con guration description of the orbitals that a particular atom s electrons occupy a Anibau Principle orbitals ll in increasing energy from lowest to highest b Pauli Exclusion Principle only two electrons can occupy an orbital and their spins must be paired c Hood s Rule 5 when orbitals of equal energy are available but there are not enough electrons to ll all of them completely one electron is added to each orbital before a second electron is added the spins of of the sin le electrons are aligned n g a r 7 p a 7 y F 7 Notation for elgectronic configuration ngt S Mme giracm bx gimme Ex Oxygen 1322322p4 39i CH 3 CH CH CC C H3 J1 H H H r Cf H l l l H l tie ache Che ce Ec l l 1 l H H 2 Octet Rule all atoms except H strive to have an outer shell of eight valence electrons which is why molecules reactform bonds Exceptions to the Octet Rule boron B and aluminum A1 are satisfied with 6 valence electrons Lewis dot structures are used to represent an atom and its valence shell electrons Steps for drawing Lewis Structures 1 Count the valence e for the molecule 2 Pick a central atom 3 Fill in bonds and lone pairs 4 Check for fonnal charge Ground State Electron Con guration N Atom W ofValencee ioferin Filled Orbital r quotBonds LonePairs H 1 p 2 f l 7 0 C 4 t 8 4 0 in 5 if s 3 7771 39o p p 6 s 2 i w 2 F1 canal s f 1 a 3 Formal Charge the charge positive negative neutral on an atom in a polyatomic ion or molecule To nd the formal charge draw the correct Lewis structure for the molecule and for each atom compare the number of valence e to the number of valence e in its neutral state If the atom has more valence e than usual it has a negative charge if it has less valence e than usual it has a positive charge a Positive 1 re atom looses a valence e L 63 it 5 2 H b Negative the atom gains a valence e Hm Cm H HafNFH iquot I t H 4 Covalent Bonds and Polarity Covalent bond fonn between atoms that share one or more pairs of electrons to give a noble gas configuration to each each atom aka to satisfy the octet rule Electronegativity a measure of the force of an atom s attraction for electrons the general trend of increasing on the periodic table is from bottom left to top right where F has the highest EN Dipole moment occurs between atoms When there is a difference in values this causes olaritv Notation t x am pi e Atom with greater EN a it as Atom with lesser EN 5 V 5 H i a 8 Ex 6563 45F 1 trooperth Bltt H r Moots moment 5 C r A CF 7 7 r Clips i O Appeal 9 m aw i 7 Arr 3w n M out CLW bgt t l if lfthe difference in EN values isr 7 7 if 7 r Xlt05 7 7 7 7 Nonpolarcovalent bond 05ltXltl9 H W 7 r r r i 7 Polar covalent bond l9ltX Ionic bond values are approximate different tentbooks will have slightly varying numbers Valence Shell Electron Pair Repulsion Theory VSEPR the idea that areas of electron density repel each other so that the geometry of bonds andor lone pairs of electrons around any one atom places these areas as far apart as possible By combing dipole moment and VSEPR theory knowledge it is possible to determine the overall molecular polarity and shape of molecules See e uquot e If r 5 Quantum Mechanics 5 There are two theories or bonding molecular orbital theory MO and valence bond theory VB 1 MO Theory 2 VB Theory W i I H Molecular Orbital Theory Valence Bond Theory tested more More accurate More useful Used to represent diatomic molecules Used to represent larger molecules Notation Notation 0 Sigma bonding sp 2 regions of electron density 0 Sigma star antibonding sp2 3 regions of electron density TE Pi bonding Sp3 4 regions of electron density n Pi star antibonding Schrodinger Equation predicts shape of orbitals involves the hybridization or mixing of atomic n Atoms come together to make bonds or to arrive at orbitals a lower energy state s Determined by regions of high electron density Having ea in antibonding MO is not favorable and 3 a Hybridized orbitals can only make sigma unstable 3 7 7 7 Herr loom tfkcs F o 9 g Tl a a s1 to M 4 2 t r 39 quot a X 1 i r H i H ig 18 39rgp3 t i H quot ix f j I CFCSPg relll S mrec DH I K 39 r S a I F J v N We tr39Ec eSo In C term s Us to Sticui H ijetquot 5 lw t g it l9 Diametery Di Geri bonds is a r l 391 t o OSF Nsp Lair 51mg e 9 LI all be Lexi S A mitts the totoesr I FEESttl looFlok H r N r1 prea C M l 3 CW We Sense HIS CEPZ 77 use Cree 939 gr r can f 6 Resonance the idea that many molecules are best described as a hybrid of several Lewis structures in other words there can be more than one equally accurate structure for a single molecule Rules for drawing resonance structures 1 Do not add electrons or change the number of valence lei 2 Do not move atoms only e The entire molecular structure should stay the same so do not change the connectivity of atoms or remove 5 bonds 3 Place negative charges on the most electronegative atoms 4 Obey the octet rule No more than 8 valence e on each atom 5 Use correct arrow pushing notation End ofthe arrow r w m 7 N 7 W W Pointofthe arrow e e atomthat can potentially donateelectronQ H W 7 an atomthat canpotentially accept electrons Found at lone pairs tr bonds atoms with negative Found at atoms with positive charge atoms that lack j charge 7 anyoctet Most contributing resonance structure characteristics Has the maximum of covalent bonds The maximum of atoms have an octet lled valence orbital Has the least of charges The negative charge is on the most electronegative atoms opposing charges should be far apart page In Ship 7 Functional Groups MEMORIZE Functional groups can be sorted into two main groups carbonyl group and non carbonyl group A carbonyl group is simply a carbon atom doublebonded to an oxygen atom 30 which includes the fanctional groups ketone aldehyde amide carboxylic acid and ester The noncarbonyl groups would include alcohol amine and ether Alcohol Aldehyde Nonacarbonyl groups can be describes as a primary 10 secondary 2 or tertiary 3 quot W quot 39 39 1 depending on how many carbons are attached Amide Amine a Amines classi ed by the number of carbon i l atoms bonded to the N itself L4 Methylamlne Dimethylamine Trimethylamine a l ai iiil w in illillllt a amino Carb oxylic acid Alcohols classi ed by on the number of carbon atoms bonded to the carbon that the OH is attahed to lil 111 tit I I misfit mi LillS etil t l curry semi Ether E1 M1 till Ester i 1quot71 alcohol A L illt ulltll A I36 illttnlml TEST TIP When identifying mctional groups within a big molecule be as specific as possible In other words don t circle a carbonyl group CZO if you can circle a carbonylic acid that the carbonyl group Ketone 5 3 J f r tquot 8 Naming Alkanes and Cycloalkanes 39 Alkanes are named according to a systematic set of rules developed by the International Union of Pure and Applied Chemistry IUPAC RULES 1 Identify the longest carbon chain if there is a cycloalkane it is automatically the main chain 2 Number the carbon chain by maximizing the number of substituents frontloading aka giving the smallest numbers possible to substituents if there is a tie between the above rules number the carbon chain using alphabetical order of substituents 3 Take note of the number of carbons in the chain because that determines the name of the main chain Name the substituents using the form carbon attached substituent name ending wiith suf x yl 5 Put it all together by listing the substituents with their numbers in alphabetical order followed by the main chain name ending in game carbon attached substituent name ending in yl carbon number suf x If there is more than one of the same substituent only write it once and use commas between carbon numbers Do not include pre xes like di trie tetra r tert or sec when alphabetizin g substituents Must include pre xes iso and neo when alphabetizing substituents There is no space between the last substituent name and the suf x Use dashes between carbon numbers and substituent names so that the entire name is connected The IUPAC name of a compound consists of three parts A pre x that tells the number of carbon atoms in the parent chain An in x that tells the nature of the carbon carbon bonds in the parent chain A suf x that tells the class to which the compound belongs Table 22 Pre xes Used in the EUPAC System to anew the Presence of 1 to 20 Carbon Atoms in U nbranched Chain Number of Number of Prefix Carbon Atoms Pre x Carbon atoms me l h undeo l 3 elhg dodeo i prop tridec 3 but 1 tetrader it pent F pentadec 3913 have n hexadece in hcpt T heptadec t nets octadec H non a nonadecv 1L9 dec 39i U eicos 2239 EX UVtPi 6quot i Number of V V S b tituem Name Line Structure carbons quota 39 1 Methyl a isceropgx B mm 6111 le 0 r 77 Fenran 8 2 Ethyl j 37 Propyl 3 Isopropyl quot 4 39 Butyl M Eemwjt egw tgcPriopt lagfzt w 39H Wl em gjl O C T041 6 4 Isnbutyl 4 Secbutyl V N 4 T 1141 F1 39quot quot f f f I e u y E 3 39quot flMi 214 S f nmcs 1tjl t m 5 Pentyl 1 Z 5 Isopentyl H K 3 VK s 2methylbu cyl i aw iso WWW quot 2 1 M mef q by MOM H ex cm ex Neopentyl 77 W 7 77 7 9 Strain and Stability f Newman Projection A way to View a molecule by looking down a carboncarbon single bond to help evaluate the relative orientations of attached groups Newman Projections are either staggered or eclipsed and jwith varying levels of strain and stability Staggered ta hi i H H t It It H ll l thi MHIJI I39I Eolipsed f TTI T39 I I ll it Hitlt39 lit u lntnrtl alumat Huim Xuxitilittl llllljt39l litm jquot Conformation Examples with Butane i Staggered Anti Confonnation soquot H iryt Hquot l a H CH3 Lowest energy STABLE j Torsional steric strain unstable Staggered GadChe iCOnformation CH3 Sterile strain stable Eelipsed Dihedral Chs 3 Highest energy Torsional sterioland angle strain LEAST STABLE A it it E l There are three types of strain an instability within a structure associated with higher internal energy a Sterie strain present in staggered and eclipsed confonnations clue to repulsion between the electron clouds of adjacent atoms 5 3 b Torsional strain present in both eclipsed oonfonnations due to loss of hyperconjugation sigma to sigma star 39 T c Angle strain only present in eclipsed dihedral confonnationhor when two big groups are stacked on top of each other due to deviation from optimum bond angle A 7 Sagger d T s 3 ii A X AI Me a x gtlt 39 ale E J Adjacent S A gtlt m x H X E yjyMH l CE 10 Chair Conformations me Came In exam At each carbona there is one axial an one equatorial hydrogen or other group Axial plane less stable try straight up or straight down not stable Equatorial plane more stable found parallel to the 2 bonds that are not connected to the attached carbon the more substituents in this plane the better 4 Axial a W 1quot Eqmdlftvr l etl 6 quot aid oli radio n A ring ip happens when one chair conformation is sewitEhed to another This means that the axial and equatorial groups switch places and the carbons physically move positions For example all the axial hydrogens become equatorial and all the equatorial hydrogens become axial These two conformations are equivalent but do not look the same EX CH ca Eli Rte 5 r I x a l w 50 clowm9 U u t t it 7 I H r I j xix X f g 1 l at q dawn 039 9 LL 6 j U UQF 1 2 CH 3 is g f f f a Uj cm are Stal0 l if fillLes he editLl t0 Gel
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