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Chapter4 - Organic Chemistry CHE 275 Chapter 4 Alcohols and...

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Organic Chemistry CHE 275 Chapter 4 Alcohols and Alkyl Halides
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• In this section chemical reactions and their mechanisms are introduced by focusing on two reactions that yield alkyl halides Overview • Both of these reactions are substitution reactions (1) alcohol + hydrogen halide ROH + HX RX + H 2 O (2) alkane + halogen RH + X 2 RX + HX
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• Organic compounds can be grouped into families • Families can be defined by their functional groups • A functional group is a collection of atoms at a site within a molecule with a common bonding pattern • The functional group reacts in a typical way, generally independent of the rest of the molecule • The functional groups also affect the reactions, structure and physical properties of every compound where they occur Families of Organic Compounds
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• Alkenes have a carbon-carbon double bond • Double bonds in simple and complex alkenes react the same way Alkenes are a Functional Group C C H H H H Br 2 Br H Br H H H H 2 C H 2 C CH CH 2 CH 3 CH 3 H Br 2 H 2 C H 2 C CH CH 2 Br CH 3 Br H 3 C H
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• Alkenes have a carbon-carbon double bond • Alkynes have a carbon-carbon triple bond • Arenes have special bonds represented as alternating single and double C-C bonds in a 6-membered ring Functional Groups With Multiple Carbon-Carbon Bonds C C C C C C C C C C Alkene Alkyne Arene (aromatic ring)
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• Alcohol: C bonded to O of a hydroxyl group (C-OH) Ether: 2 C s bonded to the same O (C-O-C) Functional Groups With Single Bonds to Oxygen C OH C O C Alcohol Ether OH ethanol O methyl tert -butyl ether (MTBE)
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Constitutional Isomerism in Functional Groups • Constitutional isomerism is not limited to alkanes • Different functional groups may have the same formulae, and therefore can be constitutional isomers • Example: butyl alcohol and diethyl ether (C 4 H 10 O) CH 3 CH 2 O CH 2 CH 3 CH 3 CH 2 CH 2 CH 2 O H diethyl ether butanol
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Different Positions of Functional Groups • Changing the position of functional group along the carbon chain will also lead to different isomers • Example: isopropyl amine and propylamine (C 3 H 9 N) H 3 C CH H 3 C N H 2 isopropylamine CH 3 CH 2 CH 2 N H 2 propylamine
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• Amine: C bonded to N (C-N) • Three types of amines (primary, secondary and tertiary) • Primary amines have one C-N bond and two N-H bonds • Secondary amines have 2 C-N bonds and one N-H bond • Tertiary amines have 3 C-N bonds Functional Groups With Single Bonds to Nitrogen C NH 2 C N C H C N C C Primary Amine Secondary Amine Tertiary Amine
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• Alkyl Halide: C bonded to halogen (C-X) (X = Cl, Br or I) • Thiol: C bonded to SH group • Sulfide: Two C s bonded to the same S (C-S-C) Other Functional Groups With Single Bonds to Carbon C Cl Alkyl Chloride C SH C S C Thiol Sulfide C Br Alkyl Bromide C I Alkyl Iodide
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Dipoles in Functional Groups • Functional groups with carbon singly bonded to an electronegative atom are polar • A partial positive charge is on C ( δ +), and a partial negative charge ( δ -) is on the electronegative atom
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