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NCSU CH 220 - Exam 2 Study Guide

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CH 220 1st EditionExam # 2 Study Guide - Be able to name alkenes using the E/Z systemo Draw a line down the double bond and assess which of the bonds has the element with the highest atomic weight attachedo Both on “zee zame zide” - Be able to name alkyneso Any organic compound with a C-C triple bondo Same naming conventions as alkenes, but using a ‘-yne’ suffix- Be able to apply Markovnikov’s rule to the reactions of alkeneso 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 ruleo Addition of water to make alcohols (as a reversible reaction) Needs heat (250C) and a catalyst (H3PO4 or H2SO4) Vapor reactiono 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 chargeo 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 configurationo 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 molecule into two pieces (or in the case of a cyclohexane,will break the ring and create a straight chain molecule)- Needs a catalyst – KmnO4- Needs an acid- Needs a solvent - H2O - Understand and be able to explain the following reactions involving alkynes:o Triple bond must be in the parent chain and get the lowest numbero Has a linear structure, not cis or trans- Addition of HX (Hydrohalogenation)o Addition of HCl or other hydrohalogeno Goes through 2 reactions 1st equivalent – goes to a double bond (1:1 ratio of alkyne and hydrohalogen) 2nd equivalent – goes to a single bond (1:2 ratio of alkyne and hydrohalogentation) How far you take the reaction depends on what the required end product is- Halogenationo Addition of Br2 or Cl2o 1st equivalent (1:1) results in a double bond with a trans configurationo 2nd equivalent (1:2) results in a single bond- Hydrogenation o Initially goes to a double bond (Cis configuration)o Then goes to a single bondo For hydrohalogenation and halogenation, you are able to measure out the reactants in order to get a 1:1 or 1:2 reaction, but with hydrogenation, because there is a huge amount of H2 that is required to be pumped into the chamber, it is impossible to measure the reactants. Instead, a catalyst can be used in order tostop the reaction at the double bond, which has huge commercial value. This catalyst is Lindler Pd and it is a proprietary compound catalyst that stops the reaction at the double bond so that it doesn’t go any


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