CHM 234: study guide
CHM 234: study guide CHM 234
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This 8 page Study Guide was uploaded by Alvin Notetaker on Sunday January 31, 2016. The Study Guide belongs to CHM 234 at Arizona State University taught by Pillai in Fall 2015. Since its upload, it has received 69 views. For similar materials see General Organic Chemistry II in Chemistry at Arizona State University.
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Date Created: 01/31/16
CHM 234: Study Guide __________________________________________________________________ Topic covered for exam: ● Radical reaction ● Alkynes ● Synthesis __________________________________________________________________ ● Radical reaction ○ Know which arrow to use ■ One head = one electron movement ■ Two head = two electron movement ○ Stability ○ Halogenation ■ For Cl 2and Br2 Remember: do not put the radical on a carbon that hNO hydrogen ○ Allylic Bromination HBr in presence of peroxide is spontaneous HCl and HI are not generally not spontaneous so, Only HBr obeys antiMarkovnikov. ● Alkynes ○ Nomenclature ■ Triple bond and double bond have equal priority, but if it is a tie, the double bonds gets the lowest number ■ ends with “yne” ■ Functional groups have higher priority than alkynes except ether and halides. Pent2yne , 2pentyne hex1en5yne ○ Acidity ■ Terminal Alkynes can be deprotonated by a very strong base such as amide ion (NH 2). ○ Preparation of Alkynes ○ Reduction of Alkynes 1. Cis Alkene a. Hydrogenation of alkynes can be stopped at alkene stage by using “poisoned” partially deactivated catalyst. b. “Poisoned” Compound: i. Lindlar’s catalyst ii. NickelBoron complex (Ni B) 2 2. Trans Alkene a. The use of sodium (or lithium) in liquid ammonia. ○ Hydrohalogenation of Alkynes With Peroxide: ○ Hydration of Alkynes: Keep in mind the if the alkynes is an internal or an terminal Keep in mind the reactants which will determine if the product is a ketone or an aldehyde. ● Hindered alkyl borane to make an aldehyde: ■ 9 BBN ■ Disiamylborane = R 2H = Sia2H ○ Halogenation of Alkynes ○ Alkylation of Terminal Alkynes and Synthesis ■ For an SN2 reaction to proceed in good yield the alkyl halide must be primary with no bulky substituents. ■ Secondary and tertiary alkyl halides undergo elimination by an E2 mechanism. ● Synthesis ○ Ozonolysis ● Ozonolysis of Alkynes ○ Oxidative cleavage with alkynes starts with ozone and water to produce carboxylic acid. Internal Alkynes .) ○ When a terminal alkynes undergo oxidative cleavage, it produces carbon dioxide. Note the reagent used between the double bond and the triple bond example. Alkylation increase skeleton size (with Acetylene ion form) Ozonolysis decreases skeleton size (with Ozone) Also learn how to synthesis compound from reactant to product using retrosynthesis , process of product to starting compound. Regiosynthesis: Synthesis: Reaction flow chart: *Taken from a review sheet from the class and written by my professor.
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