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Study guide 1

by: Juan Urquilla

Study guide 1 CH 320

Juan Urquilla


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these notes cover all of the main topics discussed in lecture and in the book. I recommend doing extra practice problems aside from the homework.
Organic Chemistry I
Dr. Colapret
Study Guide
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This 12 page Study Guide was uploaded by Juan Urquilla on Sunday October 2, 2016. The Study Guide belongs to CH 320 at University of Texas at Austin taught by Dr. Colapret in Fall 2016. Since its upload, it has received 4 views. For similar materials see Organic Chemistry I in Chemistry at University of Texas at Austin.


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Date Created: 10/02/16
Organic Chemisty Test 1 Major Topics in Chapter 1 (Covalent bonds and shape of molecules)  Formula/Functional Groups  Hybridization  Resonance structure Organic chemistry – study of compounds of carbon Difference between Isomers and Resonance Resonance – difference only in the position of their electrons Isomers – Same formula but different arrangement of atoms in molecules and different properties. Figure 1: example of isomer Figure 1: Example of resonance, only electrons change. Isomers cause molecule to have different physical properties than others. To find how many isomers in a molecule, there is a formula.. kyrocarbon – carbon that is asymmetrical, carbon attached to four different groups and not associated with any double bonds, triple bonds, methyl groups and CH2 (functional groups). n = if 2 kyrocarbons = 2 4. FUNCTIONAL GROUPS Functional Groups – atom/group within a molecule with set chemical and physical properties. (Help to determine primary, secondary, teritiary)  Alcohol -OH  Amines – N, -NH ,2-NH 3  Aldehyde  Ketone -  Carboxylic Acid -  Derivatives of Carboxylic acid – Ester = Amide = MEMORIZE : Hybridization of atomic orbitals Count how many sigma around C,N,O and pi bonds. # sigma bond = # hybridized = hybridized orbital % of S and P character Hybridization – atomic orbitals are combined form hybridized orbitials How to recognize by looking at bonds ???? Why is this important ? HYBRIDZATION ALLOWS FOR BONDING !!!! In case you forget: Between 2s and 2p = total of four orbitals hybridization affects energy level and if they will be equal. Deals with C, N, and O. P orbital has 3 atomic orbitals S orbital has 1 atomic orbital WHAT DOES SP , SP , SPMEAN ?? 3  SP = four hybridized orbitals (one s, and three p) 2  Sp = three hybridzed orbitals (one s, and two p)  SP = two hybridized orbitals (one s, and one p) 3 SP hybridization, (one s, three p) four hybridized orbitals – 109.5 Example: CH , (carbon) Sp hybrid orbitals, this is able to make four bonds one for each sp orbital such 4 as with H 2 SP Hybridization (one s, and 2 p) 120 2 Example: C H2, 4carbon) sp hybrid orbitals and p orbital are able to bond with other element, four bonds. SP Hybridzation ( one s, and one p) Example: C 2 ,2(carbon) sp hybrid orbitals and 2 p orbitals are able to make four bonds 2 for sp and 2 for p. Resonance Chapter 2: Alkanes and Cycloalkanes Hydrocarbon – compound composed of only carbon and hydrogen There are several types of Hydrocarbons: alkanes, alkenes, alkynes and arenes ALKANES ARE TETRAHEDRAL = 109.5 Alkanes: Saturated hydrocarbons Saturated hydrocarbon – carbon-carbon single bonds Alkanes called aliphatic hydrocarbons because they look like long carbon chains of animal fats Alkane general formula: C H n 2n+2 (ex: 4 carbons, H 10) Unsaturated hydrocarbons – one or more carbon-carbon double bonds, triple bonds, or benzene rings. Line-angle formula show carbons and hydrogens in a line format. pentane can also be written as CH (3H )2 3 3 Constitutional isomers: same molecular formula, different structure. IUPAC system System of prefixes to show the presence of how many atoms. (nomenclature) Alkane – single bonds (keep –ane ending) (7 carbons = hept) Alkane has two kinds of chains – parent chain (long carbon chain) and substituent chain (sticking out of main chain). Name alkanes with substituient:  Find the longest chain of carbons !!!! (choose parent with greatest number of substituents.)  Use prefix to indicate number of carbons in each substituient (ends in yl)  Give substituent lowest values when numbering.  If more than one substiuent use prefixes di, tri, tetra, etc. to show how many.  If more than one substituent, name in alphabetical order Prefix, infix, and suffix Ex: Propane (prop – 3 carbons, an – single bonds, e – hydrocarbon) Cycloalkanes (general formula C n 2n  Ex: cyclopropane  Ring structures of alkanes Naming cycloalkanes Video: Conformations of alkanes and cycloalkanes (3-D shape) Strain – measure of energy in a compound due to structural distortion. Conformation – 3-D shape of atoms resulting from single bond rotations. ( Alkanes Ex: Staggered conformation – H bond are far away from each other (most stable) Eclipse conformation – H bonds are as close as possible to each other (least stable) Newman projection – drawing down axis of C-C bond. C closest to you has lines coming from circle. LEAST INTERACTIONS = LEAST ENERGY. Gauche and anti: Gauche – relationship between atoms or groups Torsional strain – strain that arises when carbon has hydrogens that overlap butanes Cycloalkanes Small ring strain – A strain associated with ring sizes below six. Cyclopropane Cyclopropane Cyclobutane Cyclopentane Cyclohexane Chair confirmation – 3-D shape of cyclohexane (more stable, since hydrogen far away)  Axial – hydrogens that are going up or down  Equatorial – hydrogen going to the left and right The chair confirmation can be converted to the boat confirmation Boat confirmation – 3-D shape of cyclohexane (less stable, since hydrogen are close) Cis, Trans Isomerism in Cycloalkanes and Bicycloalkanes Cycloalkanes Constitutional isomers – same molecular formula but different structure Stereoisomers – different compounds with same molecular formula but different orientation of atoms. Cis – substituents on the same side Trans – substituents on opposite sides Physical properties of Alkanes and Cycloalkanes Alkanes are non-polar and only have dispersion forces Low molecular weight alkanes – gases High molecular weight alkanes – liquids Very high molecular weight alkanes – solids Least branched – high boiling point (example: Hexane because it is a straight chain. Most branched – lowest boiling point Sources and importance of Alkanes  Natural gas  Petroleum  Synthesis gas Chapter 3 Plane of symmetry – imaginary line passing through an object Center of symmetry – a point situated so that components are located on opposite sides. Chirality – molecules that are not superposable on their mirror image.  Property of whole object not individual atom Chiral – not superimposable on mirror image Achiral – superimposable mirror image Achiral molecules WILL have at least one place of symmetry. Chiral carbons – C bonded to four different groups (usually a carbon) ( THE BOTTOM PICTURE CAN HAVE THE F IN THE MIDDLE AND THE CL ON THE SIDE AND DOES MAKING IT CHIRAL. To find how many isomers in a molecule, there is a formula.. chirocarbon – carbon that is asymmetrical, carbon attached to four different groups and not associated with any double bonds, triple bonds, methyl groups and CH2 (functional groups). n = if 2 kyrocarbons = 2 4. Constitutional isomers Same things but different connectivity Stereoisomers Same things, same connectivity but 3-D shape is different Neo and Iso The prefix "iso" is used when all carbons except one form a continuous chain. This one carbon is part of an isopropyl group at the end of the chain. Common name: Common name: isopentane isopentyl alcohol IUPAC name: 2-methylbutane IUPAC name: 3-methyl-1- butanol The prefix "neo" is used when all but two carbons form a continuous chain, and these two carbons are part of a terminal Common name: neopentyl Common name: neopentane alcohol IUPAC name: 2,2-dimethylpropane IUPAC name: 2,2-dimethyl- 1-propanol


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