Chemistry Chapter 10 and 11
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1 Chemistry 2100 Chapter 10 and 11
2 Bloom s Taxonomy Richard C. Overbaugh, Lynn Schultz Old Dominion University
3 Student Objectives for this course Analyze and explain chemical differences among the various classes of organic compounds Evaluate carbohydrate structure and reactivity Compare and contrast the four main classes of key biomolecules Explain the processes of protein folding and enzymatic catalysis Use knowledge of replication, transcription, and translation to predict the outcome of genetic diseases Relate biochemical concepts to digestion, metabolism, and nutrition
4 Organic & Biological Chemistry
5 Organic Chemistry Why is organic chemistry a separate discipline within chemistry? 5! istorical: Scientists at one time believed that a vital force present in living organisms was necessary to produce an organic compound. The experiment of Wöhler in 1828 was the first in a series of experiments that led to the demise of the vital force theory.
6 IA Li Na II A 4 Be Mg II IB IV B K Ca Sc Ti Rb Sr Y Zr Cs Ba La f Fr Ra 89 Ac 104 Rf (2 23) (2 26) (2 27) (2 61) VB VIB VIIB VIII B IB II B 6 C12.01 II IA 5 B Al IV A 14 Si VA 7 N P VIA 8 O S VIIA 9 F Cl VIII A 2 e Ne Ar V Cr 25 Mn Fe Co Ni Cu 30 Zn 31 Ga 32 Ge As Se Br Kr Nb 42 Mo Tc Ru 45 Rh 46 Pd 47 Ag 48 Cd In Sn 51 Sb Te I Xe (9 8) Ta W Re Os Ir Pt Au 80 g Tl Pb Bi Po At Rn (2 09) (2 10) (2 22) 105 Db 106 Sg 107 Bh s Mt Uun 111 Uuu Uub Uuq Uuh Uuo (2 62) (2 63) (2 62) (2 65) (2 66) (2 69) (2 72) (2 77) (2 89) (2 89) (2 93) 58 Ce 59 Pr Nd 61 Pm 62 Sm 63 Eu 64 Gd 65 Tb 66 Dy 67 o 68 Er (1 45) Tm 70 Yb 71 Lu Th 91 Pa (2 31) U Np 94 Pu 95 Am 96 Cm 97 Bk 98 Cf (2 38) (2 44) (2 43) (2 47) (2 47) (2 51) 99 Es (2 52) 100 Fm 101 Md 102 No 103 Lw (2 57) (2 58) (2 59) (2 60)
7 General Chemistry element covalent bonds lone pairs 1 0 C 4 0 N 3 1 O 2 2 X 1 3 x x C x x C ~109.5
8 Valence Shell Electron Pair Repulsion Theory regions of predicted predicted electron density geometry bond angles 4 tetrahedral trigonal planar linear 180 C N ~109.5 C C 120 C N 120 C 180 C
9 Meet the Elements
10 English Language Cursive Shorthand Print Type
11 The language of Chemistry Molecular Formula 3D Structural Formula C 2 6 O Structural Formula Skeletal, line-angle Formula Condensed Structural Formula C 3 C 2 O Molecular Representation or
12 Alkanes Simplest hydrocarbons Composed of only single bonds Often referred to as aliphatic hydrocarbons From Greek aleiphar (fat or oil) Also called Paraffins From Latin parum affinis (barely reactive) General formula: C n 2n+2
13 Methane & Ethane -C- Methane -C-C- Ethane
14 Propane & Butane Ball-andstick model Line-angle formula Condensed structural formula C 3 C 2 C 3 C 3 C 2 C 2 C 3 Propane Butane
15 Butane & Constitutional Isomers C 3 C 3 C 2 C 2 C 3 C 3 CC 3 Butane 2-Methylpropane (bp -0.5 C) (bp C) C 4 10 n-butane isobutane
16 ow many constitutional isomers? constitutional (structural) isomers C ,319 C ,319 C C > 4 billion C C C C > 4 65 billion trillion > 65 trillion
17 Naming Conventions: IUPAC Nomenclature International Union of Pure and Applied Chemistry Gives a set of unambiguous names Despite this, common names are still used
18 Naming Alkanes #C Prefix + -ane C 1 C 2 C 3 C 4 C 5 C 6 C 7 C 8 C 9 C 10 "meth" Gr., methy (wine)* "eth" Gr., aithein (blaze) "prop" Gr., protos pion (first fat)* "but" L., butyrum (butter) "pent" Gr., pente (five) "hex" Gr., hex (six) "hept" Gr., hepta (seven) "oct" L., octo (eight) "non" L., nona (nine) "dec" L., deca (ten)
19 Alkyl groups Name methyl ethyl propyl isopropyl butyl Condensed Structural Formula -C 3 -C 2 C 3 -C 2 C 2 C 3 -CC 3 C 3 -C 2 C 2 C 2 C 3 Name isobutyl sec-butyl tert-butyl Condensed Structural Formula -C 2 CC 3 C 3 -CC 2 C 3 C 3 C 3 -CC 3 C 3
20 Naming Algorithm Substituents Parent Suffix IUPAC Rules (a) parent C-chain (b) substituents (c) numbers (d) alphabetical listing
21 Dreadful Details! 1. The name for an alkane with an unbranched chain of carbon atoms consists of a prefix showing the number of carbon atoms and the ending -ane. 2. For branched-chain alkanes, the longest chain of carbon atoms is the parent chain and its name is the root name. 3. Name and number each substituent on the parent chain and use a hyphen to connect the number to the name. 4. If there is one substituent, number the parent chain from the end that gives the substituent the lower number.
22 Dreadful details (part 2)! 5. If the same substituent occurs more than once: Number the parent chain from the end that gives the lower number to the substituent encountered first. Indicate the number of times the substituent occurs by a prefix di-, tri-, tetra-, penta-, hexa-, and so forth. Use a comma to separate position numbers. 6. If there are two or more different substituents List them in alphabetical order. Number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents at equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number. 7. Do not include the prefixes di-, tri-, tetra-, and so forth or the hyphenated prefixes sec- and tert- in alphabetizing; Alphabetize the names of substituents first, and then insert these prefixes.
23 Alkane Origins
24 Physical Properties of Alkanes Name methane ethane propane butane pentane Condensed Structrual Formula C 4 C 3 C 3 C 3 C 2 C 3 C 3 (C 2 ) 2 C 3 C 3 (C 2 ) 3 C 3 Mol wt (amu) mp ( C) bp ( C) Density of Liquid (g/ml at 0 C)* (a gas) (a gas) (a gas) (a gas) hexane heptane octane nonane decane C 3 (C 2 ) 4 C 3 C 3 (C 2 ) 5 C 3 C 3 (C 2 ) 6 C 3 C 3 (C 2 ) 7 C 3 C 3 (C 2 ) 8 C *For comparison, the density of 2 O is 1 g/ml at 4 C.
25 Physical Properties Solubility: a case of like dissolves like. Alkanes are not soluble in water because they are unable to form hydrogen bonds with water. Liquid alkanes are soluble in each other. Alkanes are also soluble in other nonpolar organic compounds, such as toluene and diethyl ether. Density The average density of liquid alkanes is about 0.7 g/ml; that of higher-molecular-weight alkanes is about 0.8 g/ml. All liquid and solid alkanes are less dense than water (1.0 g/ ml) and, because they are both less dense and insoluble, they float on water. 25!
26 Isomers and Physical Properties C 3 C 3 C 2 C 2 C 2 C 3 C 3 C C 3 pentane bp 36 C; mp -130 C d C 3 neopentane bp 9 C; mp -16 C d C 3 C C 2 C 3 C 3 isopentane bp 28 C; mp -160 C d 0.620
27 Alkane Origins
28 Gasoline, Combustion, & Octane Ratings C 4 + 2O 2 à CO O kcal/mol C 3 C 2 C O 2 à 3 CO O kcal/mol C6-C12 mixture but 2 C 3 C 2 C O 2 à 2 CO CO + 2 C O + < 530 kcal/mol Octane Rating Controlled Explosions Ethanol Octane rating 105 2,2,4-trimethylpentane (iso-octane) Octane rating 100 eptane Octane rating 0 Octane Octane Rating -20
29 Reactions of Alkanes Reaction with halogens (halogenation) alogenation of an alkane is a substitution reaction. 29!
30 alogenation polytetrafluoroethylene (PTFE) Teflon dichlorodiphenyltrichloroethane DDT dichlorodifluoromethane Freon Perfluorodecalin
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32 Cycloalkanes C n 2n
33 Interesting Cycloalkane Derivatives Testosterone Cholesterol Estradiol Muskone
34 Cyclohexane
35 Cyclohexane the Chair 6 C 1 C C 2 5 C 4 C "chair" C 3
36 Cyclohexane Substituents C 3 (1) (3) (3') C 3 (1) (3) 3 (3') % 5% 1,3-diaxial interactions
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48 Geometric Isomers, a.k.a. cis-trans isomers Cl Cl perspective aworth cis-1,2-dichlorocyclopentane Cl Cl Cl Cl perspective aworth trans-1,2-dichlorocyclopentane Cl Cl
49 Cis/Trans Isomers Cis: on the same side of the ring. Trans: on the opposite side of the ring, In drawing cis-trans isomers of disubstituted cyclopentanes, we can view a cyclopentane ring edge-on. 49!
50 Cis-Trans Isomers Alternatively, we can view the cyclopentane ring from above. Substituents are shown by solid wedges (above) or dashed wedges (below). 50!
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1 IA 1 ydrogen 1.01 Atomic number Element symbol Element name Atomic mass VIIIA 1 1.01 IIA IIIA IVA VA VIA VIIA 2 e 4.00 Metalloids 3 Li 6.94 4 Be 9.01 5 B 10.81 6 C 12.01 7 N 14.01 8 O 16.00 9 F 19.00
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