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CHM 234: study guide

by: Alvin Notetaker

CHM 234: study guide CHM 234

Alvin Notetaker
GPA 3.33

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Reactions of elimination and addition that is needed to be learned before the test.
General Organic Chemistry II
Study Guide
Organic Chemistry
50 ?




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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​ 2​and 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​ 2​H = Sia​2​H    ○ 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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