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CHM 234| Study Guide for exam 2

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by: Alvin Notetaker

CHM 234| Study Guide for exam 2 CHM 234

Marketplace > Arizona State University > Chemistry > CHM 234 > CHM 234 Study Guide for exam 2
Alvin Notetaker
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Topic: Alcohol & Phenol Ethers & Epoxides Thiols and Sulfides The Conjugated Pi Systems and Pericyclic Reactions is not in this guide.
General Organic Chemistry II
Study Guide
Organic Chemistry
50 ?




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This 12 page Study Guide was uploaded by Alvin Notetaker on Sunday February 28, 2016. The Study Guide belongs to CHM 234 at Arizona State University taught by Pillai in Fall 2015. Since its upload, it has received 172 views. For similar materials see General Organic Chemistry II in Chemistry at Arizona State University.


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Date Created: 02/28/16
CHM 234: Study Guide Exam 2  __________________________________________________________________  Topic:  Alcohol & Phenol  Ethers & Epoxides  Thiols and Sulfides  __________________________________________________________________    Alcohol & Phenol:  ● Nomenclature  a. Find the parent chain which should include the hydroxyl group.  b. Find the substituents and name them.  c. The hydroxyl group should have the lowest number. (Have the most priority)  d. Put the name in alphabetical order  e. the suffix ends with “­ol” instead of “­e”.  ● ­OH have more precedence over the others like double bonds.  ● On cyclic alcohols, the ­OH group is one carbon 1 and it is omitted    Type  Primary alcohol  Secondary alcohol  Tertiary alcohol  Structure          ● When a ­OH group is on a benzene ring, it is called, phenol.        ● Deprotonation of an alcohol compound will produce an alkoxide ion  ○ Reagent: NaH  ● Solvation Effects  ○ Less sterically hindered = more easily solvated  ○ More sterically hindered = less easily solvated    Primary substrate→S​ 2→strong nucleophile  N​ Tertiary substrate→S​ 1→weak nucleophile  N​ (First arrow = requires / second arrow = will be)    Addition of ­OH  Acid­catalyzed Reaction (H O, 2cid)  Mercuration­demercuration Reaction (Hg(OAc) , H SO  with NaBH )  2 2 4 4 Hydroboration­Oxidation Reaction (BH , THF 3ith H O , NaOH)2 2   Oxidation state    Reducing Agent to form ­OH  Catalytic Hydrogenation (H  wi2h Pt, Pd, or Ni)  Sodium borohydride (NaBH  with 4eOH, EtOH, or H O)  2 Lithium aluminum hydride (LAH with H O)  2   LAH is more reactive than NaBH​  and will react witcarboxylic acid and ester to give alcoh. ​ 4​     Diols  ● Have two hydroxyl group  ● In naming, the “diol” is put in the end of the name.      Dihydroxylation  Reagent:  ● RCO H  (Causes ​ trans​diols)  3 + ● MCPBA with acid (H )(Causes ​ trans diols)  ● OsO  with NMO or tert−butyl hydroperoxide(Causes c ​isdiols)  4 ● KMnO  w4th NaOH (Causes c ​i diols)      Grignard reaction to form ­OH  General skeleton: R­Mg­X  ● Reagent: Mg with dry ether    To form the ­OH:  ● Reagent: Grignard reagent with H O2   Protection of ­OH  For protection:  ● Reagent: TMS−Cl with Et N t3 form TMSO  To deprotect:  + − ● Reagent: H O3, F  (TBA−F)    Reaction of Alcohols: Substitution and Elimination  SN​ reaction with 3°  SN​ reaction with 1°    Reagent for Substitution:  ● HBr  ● HI  ● HCl with ZnCl   2 ● TsCl, Pyridine with halide(goes for SN​)  ● SOCl  with Pyridine (1° and 2°, goes for S2)  2 N​ ● PBr 3or PCl  3ith Pyridine  ○ Carbocation rearrangement is avoided    Reagent for Elimination:  ● conc. H2SO 4with heat(E1 reaction)  ● TsCl, Pyridine with NaOEt(E2 reaction)    Note: remember to know how to do ring expansion    Oxidation  Reagent:  ● Strong (to form chromic acid)  ○ CrO 3with acetone  ○ Na 2r 2  7ith H S2 , 4 O 2 ● Mild  ○ PCC with CH Cl2  2         Na​Cr​O​  / HSO​ PCC / CH​ Cl​ 2​ 2​ 7​ 2​ 4  2​ 2  2α­H  1° alcohol  Acid  Ketone    1α­H  2° alcohol  Ketone  Ketone    0α­H  3° alcohol  None  None          Phenol still undergo oxidation even though it does not have an alpha hydrogen.    Ethers & Epoxides:  Nomenclature  1. Name each ­R group  2. Arrange alphabetically  3. End with “ether”    IUPAC names  1. Parent chain: larger ­R group  2. Name the smaller ­R group “alkoxy substituent”    Structure and Properties of Ethers  Bond angle is similar to water and alcohol  Hydrogen bond acceptor, not hydrogen bond donator  ● Meaning that it can interact with protons like in alcohol, but not with itself.    Crown Ether  X­Crown­Y  ● X ­ Total number of atom in crown  ● Y ­ Total number of oxygen atom    12­Crown­4      The fluorine anion is very reactive because the potassium cation bonded itself to the crown ether.  ● Crown ether is called host.  ● The metal atom, for example, the K​ + ion,  is called guest.  Smaller crown binds to smaller cation.    Preparation of Ether  Prepared by acid­catalyzed dehydration of ethanol  ● Symmetrical ether only  Williamson Ether Synthesis  ● Can be for non­symmetrical and symmetrical ether  ● Halide goes on less hindered alkyl group  ● Alkoxide ion goes on more hindered alkyl group        Alkoxymercuration–Demercuration  Reagent: Hg(OAc) , Alco2ol with NaBH   4     Reactions of Ether  Acid cleavage  ● Ether is a poor leaving group  ● Only HBr and HI can be used because they are strong acid and good nucleophile    When phenyl ether is under cleavage, it will produce a phenol and an alkyl halide. Neither of the  two substitution reaction will work because of the sp​ 2 hybridization    If The ­R group a secondary carbocation, the reaction will be a S​ N​ reaction because it is faster.    Nomenclature of Epoxides                                                Oxirane               Oxetane                 Oxolane               Oxane    Oxiranes = Epoxides         Nomenclature  1. Oxygen is given the 1­position  2. Naming similar to alkane, but an “epoxy” is placed into the name for the carbon bonded  to the oxygen.  Epoxides are not substituents, thus it does not get the same rule as other substituents like methyls  and ethyls. So when writing the prefix “epoxy”, the word goes before the parent chain’s name.    Preparation of Epoxides  Reagent:  ● RCO H   3 ● MCPBA    Preparation from Halohydrins  Reagent:  ● Br2 with H2O(To form Halohydrin)  ● Br  with H O, then NaOH (To form Epoxide)  2 2         Enantioselective Epoxidation  Select one of the two enantiomers.  Reagent:  ● Ti[OCH(CH​ 3​24​with (±)­DEM    (Sharpless catalyst)  ○ +: above plane  ○ ­: below plane  ● t­butyl hydroperoxide  Only with allylic alcohol    The orientation when drawing the Sharpless asymmetric epoxidation, the hydroxyl group is at  the upper right corner.      Ring­Opening Reactions of Epoxides  Epoxides are more reactive than ethers because of the stress in the three­member ring in a  nucleophilic substitution reaction. The ring will open up as a result of reacting.    nucleophile will attack the l ​ess substituted position.    Acid­Catalyzed Ring Opening  nucleophile will attack the m ​ore ​ substituted position  .      Will attack  Dominant factor  1° vs. 2°  1°  steric effect  2° vs. 3°  3°  electronic effect  1° vs 3°  3°  electronic effect      Thiols and Sulfides   Thiol = ­SH  When naming, the compound ends with “thiol” instead of “ol”  Thiols are also known as mercaptans  “mercapto” is used when thiols are a substituent    Preparation of Thiol  Reagent  ● NaSH   Thiols can be prepared with a S​ 2 reaction with sodium hydrosulfide (NaSH) and alkyl halide.  N​     Sulfides  Similar structure to ether with oxygen, ether structure with sulfur are called sulfides or  thioethers.                diethyl ether                                 diethyl sulfide    Prepared by nucleophilic attack of a thiolate on an alkyl halide      SAM  S­Adenosylmethionine (SAM) is a good biological methylating agent  Same effect can happen with methyl iodine.    Methylation is the process of substituting methyl group into the molecule, replacing the  hydrogen atom.     


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