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CH 220 1st Edition Final Exam Study Guide  Recognize and be able to explain the difference between ionic and covalent bonds.  Be able to draw Lewis structures for compounds containing C, N, O, H, F, Cl, Br, and I.  Be able to explain the concept of hybridization, and recognize the type of hybridization in a given carbon center and the number of hybrid orbitals in a given structure.  Be able to explain what a polar covalent bond is, and be able to determine the direction of expected polarity for a given molecule.  Be able to identify constitutional (or structural isomers).  Be able to draw extended, condensed, and bond-line structures of alkanes and cycloalkanes.  Be able to recognize basic functional groups (all the functional groups in the worksheet I sent you).  Using IUPAC rules, be able to name alkanes, haloalkanes, and cycloalkanes.  Be able to recognize and draw cis- and trans- isomers in disubstituted small ring systems (cycloalkane with two substituents).  Be able to draw and identify axial and equatorial substituents in cyclohexane and recognize the lower energy conformers in systems with more than one substituent.  Recognize alkenes and cycloalkenes and be able to name them using IUPAC nomenclature.  Recognize primary, secondary, and tertiary carbons.  Be able to name alkenes using the E/Z system o Draw a line down the double bond and assess which of the bonds has the element with the highest atomic weight attached o Both on “zee zame zide”  Be able to name alkynes o Any organic compound with a C-C triple bond o Same naming conventions as alkenes, but using a ‘-yne’ suffix  Be able to apply Markovnikov’s rule to the reactions of alkenes o Hydrohalogenation and Hydration use follow Markovnikov’s rule – the Hydrogen will always bond to the carbon with the most Hydrogen neighbors  Understand and be able to explain electrophilic addition reactions involving alkenes: o Addition of HX (hydrohalogenation) with mechanism  Goes through a carbocation phase  Markovnikov’s rule o Addition of water to make alcohols (as a reversible reaction)  Needs heat (250C) and a catalyst (H3PO4 or H2SO4)  Vapor reaction o Addition of halogens (Cl-Cl and Br-Br) with mechanism  Cannot use F (too explosive) or I (not reactive enough)  Has a triangular intermediate – the Br or Cl gains the charge o Addition of H2  Requires Pt, Pd, Ni or PtO2 and a solvent  Reaction doesn’t happen in a solution, but rather on the face of the catalyst  Always results in a Cis configuration o Oxidation reactions (in acid as well as base, skip the epoxidation reaction).  Hydroxylation  Adding of 2 x OH groups  Has a Syn mechanism, resulting in a Cis configuration  Needs a catalyst – KmnO4  Needs a base – NaOH  Needs a solvent – H2O  Results in a Vicinal Diol (neighboring OH)  Oxidative cleavage  Breaks a ...

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