Familiarize yourself with the principal functional groups of organic chemistry

Transcription

1 Chemistry 261 Laboratory Experiment 1: Model Building Reading from Zubrick, 10 th Edition (for Live Labs Beginning Next Week) Safety, pages 1-10 Keeping a Notebook, pages Mining Your Own Data, pages Objectives Familiarize yourself with the principal functional groups of organic chemistry Use the rules of organic nomenclature to unambiguously name organic compounds Develop a sense of the 3-dimensional structure associated with organic compounds Procedure Obtain a model kit and construct models for the following compounds. Once you have done so, write the structural and bond-line formulas in the space provided, and indicate what family of organic compounds the compound belongs An appendix has been attached which provides the information you need concerning functional groups, the names of the first 10 unbranched alkanes and their role in nomenclature, the basic rules of nomenclature, and the naming and use of substituents Feel free to ask questions as you proceed!

2 #1: Pentane #2: 2,2-Dimethylpropane #3: 2-Methyl-2-butene

3 #4:trans-2-Butene #5: Cyclopentane #6: trans-1,2-dimethylcyclopentane

4 #7: cis-1,3-dimethylcyclohexane #8: 2-butyne #9: Isopropanol (2-propanol)

5 #10: trans-2-chlorocyclohexanol #11: cis-3-methylcyclohexanol #12: Diisopropyl ether

6 #13: Benzene (1,3,5-cyclohexatriene) #14: Anisole (methoxybenzene, methyl phenyl ether) #15:Benzaldehyde (formylbenzene or phenylmethanal)

7 #16: Acetophenone (acetylbenzene or phenyl methyl ketone) #17: Acetone (2-propanone) #18: Ethanal (acetaldehyde)

8 #19: Ethanoic acid (acetic acid) #20: Ethyl ethanoate (ethyl acetate) #21: Pyruvic acid (2-ketopropanoic acid, 2-oxopropanoic acid)

9 #22: (S)-Lactic acid ((S)-2-hydroxypropanoic acid) #23: Triethyl amine #24: Cadavarine (1,5-diaminopentane or 1,5-pentanediamine)

10 #25: Acetamide (ethanamide) #26: Dimethyl formamide (DMF, N,N-dimethylmethanamide) #27: Vanillin (4-hydroxy-3-methoxybenzaldehyde)

11 #28: Cinnamaldehyde (trans-3-phenyl-2-propenal) #29: Amphetamine ((S)-1-methyl-2-phenylethanamine) #30: Methamphetamine ((S)-N,1-dimethyl-2-phenylethanamine)

12 Appendix A: The Common Functional Groups of Organic Chemistry

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14 Appendix B: The First 10 Linear Hydrocarbons IUPAC Base Prefixes #C Base As Parent Alkane As Substituent 1 Meth- Methane Methyl 2 Eth- Ethane Ethyl 3 Prop- Propane Propyl 4 But- Butane Butyl 5 Pent- Pentane Pentyl 6 Hex- Hexane Hexyl 7 Hept- Heptane Heptyl 8 Oct- Octane Octyl 9 Non- Nonane Nonyl 10 Dec- Decane Decyl 1 C: Methane 2 C: Ethane Molecular formula: CH 4 Molecular formula: C 2 H 6 Condensed structural formula: CH 4 Condensed structural formula: CH 3 CH 3 N/A When used as a substituent: methyl When used as a substituent: ethyl 3 C: Propane 4 C: Butane Molecular formula: C 3 H 8 Molecular formula: C 4 H 10 Condensed structural formula: CH 3 CH 2 CH 3 Condensed structural formula: CH 3 (CH 2 ) 2 CH 3 When used as a substituent: propyl When used as a substituent: butyl

15 5 C: Pentane 6 C: Hexane Molecular formula: C 5 H 12 Molecular formula: C 6 H 14 Condensed structural formula: CH 3 (CH 2 ) 3 CH 3 Condensed structural formula: CH 3 (CH 2 ) 4 CH 3 When used as a substituent: pentyl When used as a substituent: hexyl 7 C: Heptane 8 C: Octane Molecular formula: C 7 H 16 Molecular formula: C 8 H 18 Condensed structural formula: CH 3 (CH 2 ) 5 CH 3 Condensed structural formula: CH 3 (CH 2 ) 6 CH 3 When used as a substituent: heptyl When used as a substituent: octyl 9 C: Nonane 10 C: Decane Molecular formula: C 9 H 20 Molecular formula: C 10 H 22 Condensed structural formula: CH 3 (CH 2 ) 7 CH 3 Condensed structural formula: CH 3 (CH 2 ) 8 CH 3 When used as a substituent: nonyl When used as a substituent: decyl

16 Appendix C: The Basic Rules of Nomenclature The 2 major rules of alkane nomenclature: 1. Assign the longest possible parent/carbon chain 2. Number substituents begin numbering at one end of the parent chain - to give the lowest number to any substituent. And 2 lesser (but important) rules: 3. If there is more than one substituent, start numbering from the end that gives the lowest number to the substituent encountered first. 4. If you have more than 1 of the same substituent, indicate the location via the numbering system and use the prefix di-, tri-, tetra- 5. List substituents in alphabetical order, bearing in mind that the di, tri, iso, etc. prefixes do not count Helpful pointers: From the name we should be able to unambiguously deduce the structure this is a good check to make certain you have included all of the pieces In molecules that have multiple functional groups, the group with the highest oxidation state takes priority you can expect a carboxylic acid (necessarily on the end of the molecule) will be position 1. Thus it is important to know how to name other functional groups as a substituent o An R-OH group is termed hydroxy (R is some chunk o carbon) o An R-Cl group is chloro o An R-Br group is bromo o An R-I group is iodo o See board for alkyl substituents with different branching configurations isopropyl isobutyl sec-butyl tert-butyl