Organic Chemistry, Week 5
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This 15 page Class Notes was uploaded by Pratiti Ghosh-Dastidar on Sunday October 2, 2016. The Class Notes belongs to 251 at Miami University taught by Dr. Gung in Fall 2016. Since its upload, it has received 4 views. For similar materials see Organic Chemistry 1 in CHM at Miami University.
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Date Created: 10/02/16
Pg-31 Isopropyl methyl cyclohexane is not chiral 1,2 – di methyl cylohexane has cis- and trans- isomers o Cyclohexane V. Cyclopropane Gauche interactions present in both isomers (cis- and trans-) NOTE: We want larger substituent in equatorial position so it doesn’t interact with the Hydrogen in the ring ((more stable). o Axial position possesses steric Strain. Bicyclic Compounds o 3 Classes: 1 Spiro (1 C Shared) 2. Fused bicyclic (2 C Shared) 3. Bridged bicyclic (3 C shared) Pg – 32 1. Spiro Compound 3D Shape: not adequetely reflected by 2D drawing. a. The 2 rings must lie in different perpendicular planes 2. Bi Cyclic – Shares 2 or more Carbons (more prevalent in nature than spiro) Ex) 3. The 2 ndmay fuse on to that first at positions, either cis- or trans- to one another 4. When fusing the 2 ndring onto cyclohexane, it’s important to recall that axial/equatorial sites are different: Trans-diaxial fusion impossible Trans-diequatorial fusion possible. Pg -33 Naming bicyclic compounds: Counting the number of Carbons in the ring system; this gives a base name (i.e. a bicyclic with 8 carbons have a base name “octane”) Number from the bridged (c#1) along the longest bridge first, then the next longest, then the shortest (if there are three bridges) Assign each bridge a number equal to the number of carbons (excluding bridge heads); put those numbers in brackets in ascending order, separated by periods between a “bicycle” suffix and base name. Polycyclic Compounds: Polycyclic can have important applications. Cholesterol is a naturally occurring compound that impacts our health, while tricycloillinone (isolated from wood of Illicium tashiroi) is potential drug for Alzheimer’s disease. o Quite stable compound b/c entirely composed of fused cyclohexanes structures. Ex) diamonds are infinite network of adamantine Pg-34 Review and Preview o A low Pkandicates strong acid (a good proton donor) o Presence of electronegative elements bound to C leads to more polar species o Polar compounds are generally more reactive than unstrained nonpolar compounds. Alkyl Halydes: Nomenclature o CnH2n+1 X= F, Cl, Br or I o Systematic nomenclature is same as alkanes: halides are named as a substituent and listed according to regular numbering and alphabetizing rules Ex) F=Fluoro, Cl=Choloro, Br=Brome and I=iodo Common Names o As molecular weight inc. bp and mp increases Alkyl halides classified based on how alkyl group is attached: (methyl, primary, secondary, tertiary, vinyl) Pg – 35 Alchols o Replace “e” of the alkane parent with “ol” o Give OH group lowest possible number Other common names to memorize Amines o Derivatives of ammonia 1,2, or 3 H atoms are replaced to give primary, secondary, or tertiary amine Pg – 36 X o Primary amines: Name R group and add the suffix “amine” o Higher amines order alkyl substituent alphabetically followed by suffix “amine” o Another way to name primary amines: name them as substituted alkanes with “amino” to designate the NH2 substituent NOTE: Amines are just below alcohols in terms of priority for lowest number when naming Cyclic compounds w/N in the ring have common names: Pg – 37 Amonium Salts (ionic comp.) list substituents alphabetically, followed by “ammonium”, then the name of the counter anion Ethers o 2 ways to name them IUPAC way consider the longest substituent as the parent chain and to name the shorter and the O together as an alkoxy substituent. Common way is to name the 2 groups and list them alphabetically followed by the word “ether” Pg – 38 Alkyl halide: Structure o Carbon and fluorine have similarly sized orbitals overlap well, making strong bonds. Larger halides form progressively weaker bonds to carbon Alcohols are structurally similar to water o The C-N bond length in an amine is between the length of an alkane C-C bond and alcohol C-O bond. Note: o Almost all amines rapidly undergo an “umbrella & flip” at equilibrium hybridized N in the transition state
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