Chapter 4 - Introduction to Functional Groups Alcohols and...

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Introduction to Functional Groups Alcohols and Alkyl Halides (Introduction to Organic Mechanisms) Chapter 4 Functional Groups • A structural unit in a molecule responsible for its reactivty and physical properties • Reactive point of a molecule. • Most organic compounds have C—C and C—H bonds. • However, many organic molecules possess other structural features: – Heteroatoms —atoms other than carbon or hydrogen. π Bonds—the most common π bonds occur in C—C and C—O double bonds.
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When a benzene ring is bonded to another group, it’s called a phenyl group . Functional Groups • Heteroatoms and π bonds confer reactivity on a particular molecule. Heteroatoms have lone pairs (electron rich) and create electron deficient sites on carbon.
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Functional Groups Functional Groups Hydroxy groups leads to dramatically different properties No polar bonds, no lone pairs, no reactive sites b relatively inert
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Carbonyl Groups (C=O) Functional Groups Containing C=O
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Be able to identify all functional groups in ________________ Alcohols and Alkyl Halides
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Most widely used are: Functional class nomenclature _________________________ Substitutive nomenclature _____________________________ Both types can be applied to alcohols and alkyl halides. IUPAC Nomenclature There are several kinds of IUPAC accepted nomenclature. Name as halo-substituted alkanes. Number the longest chain containing the halogen in the direction that gives the lowest number to the substituted carbon. Substitutive Nomenclature Haloalkanes CH 3 CH 2 CH 2 CH 2 CH 2 F CH 3 CHCH 2 CH 2 CH 3 Br 1-fluoropentane 3-iodopentane 2-bromopentane CH 3 CH 2 CHCH 2 CH 3 I
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Halogen and alkyl groups are of equal rank when numbering the chain. Number the chain in the direction that gives the lowest number to the group (halogen or alkyl) that appears first. CH 3 Cl Cl CH 3 Substitutive Nomenclature Alkyl Halides Name as "alkanols." Replace -e ending of alkane name with -ol . Number chain to give lowest locant to the carbon that bears the -OH group. CH 3 CH 2 OH CH 3 CHCH 2 CH 2 CH 2 CH 3 OH CH 3 CCH 2 CH 2 CH 3 OH CH 3 Substitutive Nomenclature Alcohols ethanol 2-hexanol or hexan-2-ol 2-methyl-2-pentanol or 2-methylpentan-2-ol
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CH 3 Hydroxyl groups outrank alkyl groups when numbering the chain. Number the chain in the direction that gives the lowest number to the carbon that bears the OH group CH 3 OH Substitutive Nomenclature Alcohols • Alcohols and alkyl halides are classified as primary secondary tertiary according to their "degree of substitution." • Degree of substitution is determined by counting the number of carbon atoms directly attached to the carbon that bears the halogen or hydroxyl group. Classification
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This note was uploaded on 12/22/2011 for the course CHEM 3371 taught by Professor Anderson,k during the Fall '08 term at Southern Methodist.

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Chapter 4 - Introduction to Functional Groups Alcohols and...

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