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CHM 234: Synthesis and Alcohol

by: Alvin Notetaker

CHM 234: Synthesis and Alcohol CHM 234

Marketplace > Arizona State University > Chemistry > CHM 234 > CHM 234 Synthesis and Alcohol
Alvin Notetaker
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Lecture 5 and 6 notes
General Organic Chemistry II
Class Notes
Organic Chemisrty
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This 9 page Class Notes was uploaded by Alvin Notetaker on Saturday January 30, 2016. The Class Notes belongs to CHM 234 at Arizona State University taught by Pillai in Fall 2015. Since its upload, it has received 35 views. For similar materials see General Organic Chemistry II in Chemistry at Arizona State University.

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Date Created: 01/30/16
Synthesis:   I. Functional Group Transformations:  __________________________________________________________________  Review:    ● Elimination reaction​  is based on thebase​ used to determine whether the more or less  substituted alkene​  is formed.   ● Addition reaction​  is based on whether peroxide​ is used to formanti­Markovnikov or  Markovnikov addition.​     ● Hydroxyl from must be made into a better leaving group like ​ TsCl with pyridine​ .    ● Regiochemical outcome can be​  manipulated​  by choice of reagents.    __________________________________________________________________  II. Reactions that Change the Carbon Skeleton:    A. Increasing Carbon Skeleton  ● Alkylation of a terminal alkyne increases the carbon.    B. Decreasing Carbon Skeleton  ● Ozonolysis ​ of Alkene  ○ C=C is reactive toward oxidative cleavage  ○ Ozone is in resonance      Example:      ● Ozonolysis of Alkynes  ○ Oxidative cleavage with ​ alkynes​  starts withozone and water​  to  produce carboxylic acid​ . ​nternal Alkynes​.)    ○ When a ​ terminal alkynes​  undergo oxidative cleavage, it produces  carbon dioxide​ .    Example:      III. Retrosynthetic Analysis: Synthesis Backwards    ○ Retrosynthetic Analysis​  is the process of mentally breaking down a molecule  into the starting molecule.  ○ Target Molecule​  is the molecule to be synthesized.   ○ Retrosynthetic arrow​  indicate a reverse reaction.  ○ Synthon​  are fragments resulting from a disconnection.    ● Approaching synthesis problem:  ○ Ask how the carbon chain has changed  ○ Ask how the functional group has changed.  1)    Regiosynthesis:    Synthesis:        2)      Regiosynthesis:    Synthesis:      Alcohol:    1. Structure and Properties of Alcohols  ● 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.  d. Put the name in alphabetical order  e. the suffix ends with “­ol” instead of “­e”.    ■ Replace “­e” with “­ol”  Pentane  Pentan­1­ol , 1­pentanol  ■ Longest chain  Parent:​Hexane  Parent:Pentanol  ■ ­OH have more precedence over the others like double bonds.  (Bottom numbers are correct)  ■ Name placement: just before the parent name or just before the ­ol suffix  Pentan­3­ol , 3­pentanol  ■ R and S should be place before the name.  (R)­2­chloro­3­phenylpropan­1­ol  Phenyl  ■ On cyclic alcohols, the ­OH group is one carbon 1 and it is omitted  Cyclopentanol  (R)­3,3­dimethylcyclopentanol  ■ Common names  isopropyl alcohol tert­Butyl alcohol Benzyl alcohol  Benzyl  ● Classification of Alcohols  Type  Primary alcohol  Secondary alcohol  Tertiary alcohol  Structure          ● When a ­OH group is on a benzene ring, it is called, phenol.  Phenol 4­chloro­2­nitrophenol  ● Commercially Important Alcohols  ○ Methanol  ○ Ethanol  ○ Denatured alcohol​  ­ ethanol with small toxin compound (such as methanol)  ○ Isopropanol​   ­ industrial solvent, antiseptic and as a gasoline additive  ● Physical properties of Alcohols  Boiling point =  −89°C   Boiling point =  12°C   Boiling point =  78°C   ○ Since they can H­bond, they can attract water strongly    ○ Alcohols with a small carbon chain are miscible in water  (Right: Hydrophobic , Left: Hydrophilic)  ○ The larger the chain, the less miscible        2. Acidity of Alcohols and Phenols  ● Acidity of the Hydroxyl Functional group    ● Reagents for Deprotonating an Alcohol  ○ Deprotonation of an alcohol compound will produce an ​ alkoxide ion    ● Factors Affecting the Acidity   ●   ○ Resonance  Cyclohexanol  pka= 18  Phenol  The resonance­stabilized anion is called a phenolate​ or a phenoxide​  ion  pka= 10    ○ Induction  Ethanol  pka= 16    Trichloroethanol  pka= 12.2    ○ Solvation Effects  ■ Less sterically hindered = more easily solvated  ■ More sterically hindered = less easily solvated 


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