hapter 3 rganic hemistry 3.1-3.3, 3.5, 3.8-3.10 ydrocarbons, Alkanes: ecognizing rganic Structures ydrocarbons: Alkanes, Alkenes and Alkynes: ecognizing Isomers and Basic Naming of ydrocarbons Identifying Functional Groups in General ecognizing and Naming Basic Functional Groups Basic eactions, Polymer Synthesis and Properties 1100-hapter3-Fall005 1 3.1-3.4 ydrocarbons ydrocarbons (s): rg cmpds w and only. Alkanes (, no double bonds), Alkenes, Alkynes Alkanes:,, no multiple bonds. = rest of molecule that does not contain the functional group. Usually remainder is just, with no reactive bonds. eactions of : can be oxidized, mostly burn (oxidation). 1100-hapter3-Fall005 3.9 Alkenes, Alkynes. s w Fnc Groups Alkenes 3 3 3 3 Alkynes 1100-hapter3-Fall005 3 1
Alkanes: Isomers vs otation 3 3 3 3 Saturated (All s have 4 bonds, All Single Bonds; no double or triple bonds) hemical formula of noncyclic hydrocarbon alkanes: n = # and n + = # s 1100-hapter3-Fall005 4 Structural Isomers Parent Molecule Isomer (iso=same and mer = part). Isomers = different molecules w same formula. Three molecules below. Which is the same molecule? Which is a structural isomer (different molecule, same formula)? Which is a completely different molecule (different chemical formula). I II III 1100-hapter3-Fall005 5 3.5 Naming Alkanes #1 Basic Parts to Names of rganic Molecules: Prefix + Ending Prefix: Tells number of carbons in longest continuous chain Ending: identifies chemical family based on functional group. Alkane Names: Prefix + ane or prefixane Alkene Names: Prefix + ene or prefixene Alkyne Names: Prefix + yne or prefixyne 1100-hapter3-Fall005 6
3.5 Naming Alkanes #: Prefixes # arbons (in longest continuous chain) 1 3 4 5 6 7 8 9 10 Prefix Example Methane Ethane Propane Butane Pentane exane eptane ctane Nonane Decane 1100-hapter3-Fall005 7 3.5 Examples Prefix 1. ount carbons to find longest continuous chain. This gives the parent chain. ane (Ex. Below: octane). Number the main chain carbons so substitutent has lowest possible number. Name substituent as # yl ane. (Ex. Below: 3-propyloctane) 3 4 5 6 7 8 1 1100-hapter3-Fall005 8 3.5 Naming Alkanes #3: Branches Prefix Meth- Eth- Prop- But- Pent- ex- ept- ct- Non- Dec- Meth- Eth- Prop- But- Pent- ex- ept- ct- Non- Dec- Meth- Eth- Prop- But- Pent- ex- ept- ct- Non- Dec- Naming a Branch: Prefix + yl 1100-hapter3-Fall005 9 3
3-ethyl-1-pentene 3-ethylheptane 3.8 ecognize and Name Alkenes and Alkynes 1. ount carbons to find longest chain that contains the multiple bond. This gives the parent chain.. Number the main chain carbons so multiple bond has lowest possible number. Name cmpd as # ene or # yne. Example: Main chain has 6 carbons. ex 3 as a multiple bond exene From left to right: ene starts at 4 From right to left: ene starts at. Name: -exene 3 1100-hapter3-Fall005 10 3.8 Functional Groups Functional groups: multiple bonds: =, =, etc. others have N,, S, alogens, etc. N Examples: N = Alcohols 3, 3, 3 ( ) 0 N = Amines 3 N, 3 N, 3 ( ) 4 N X = aloalkanes (also called alkyl halides) 3 l, 3 Br etc. 1100-hapter3-Fall005 11 Examples 1. Find longest continuous chain w functional group (if present). 3. Number chain in direction to give fnc grp lowest possible number, or substituent lowest possible number. 3. Name parent chain. If fnc grp then add #- for fnc grp. If substituent add #- yl for substituent. 3 3 3 3 1100-hapter3-Fall005 1 4
Functional Groups to Know Alkanes, alkenes, alkynes: Alcohols: - Amines: -N -N- -N- -N- - - arboxylic Acids: Ester: -- -- (arbonyl - part of many functional groups.) Amide: --N 1100-hapter3-Fall005 13 eactions to Know adical Addition: across a double bond ( vinyl polymers). Addition pzn. ondensation Polymerization: gives polyesters and polyamides. a. Dicarboxylic acids with Diols to polyesters. -- + - - - ==> ~~ ~~ b. Dicarboxylic acids with Diamines to polyamides. -- + N- -N -N ==> ~~N N~~ 1100-hapter3-Fall005 14 Addition Polymerization Given monomer be able to make the polymer. 3 l 3 Given polymer be able to give the monomer. 1100-hapter3-Fall005 15 5
ondensation Polymerization Polyesters: Diacid and Diol ---- + -- ------ --- --- ----- --- -- (-) 1100-hapter3-Fall005 16 ondensation Polymerization # Polyamides: Diacid and Diamine ---- + N--N N--N--- -N--N 1100-hapter3-Fall005 17 Sample Problems l 3 3 1100-hapter3-Fall005 18 6