CEE 370 Environmental Engineering Principles
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1 Updated: 4 October 05 Print version CEE 370 Environmental Engineering Principles Lecture #8 Environmental Chemistry VI: cidsbases III, Organic Nomenclature Reading: Mihelcic & Zimmerman, Chapter 3 Davis & Masten, Chapter Mihelcic, Chapt 3 David Reckhow CEE 370 L#8
2 Steps in Solving chemical equilibria. List all chemical species or elemental groupings that are likely to exist Cations: Na,, Ca, N 4,, etc. nions: NO 3-, Cl -, SO - 4, O -, PO -3 4, PO - 4, PO 4-, c -, CO 3-, CO - 3, etc. Neutral species: N 3, c, 3 PO 4, CO 3, etc. note that ionic salts (e.g., NaCl, Cl) completely dissociate in water an thus should not be listed. David Reckhow CEE 370 L#8
3 Showing an example of 0-3 NaCO 3 added to water Steps in Solving chemical equilibria (cont). List all independent chemical equations that involve the species present, including: C carbonates. Chemical Equilibria E.g., acid base equilibria B. Mass Balance equations Total amount of each element is conserved 3 CO3 CO3 CO3 0 and C. Electroneutrality or charge balance CO 0 CO ll water solutions must be neutrally charged CO CO3 Na O CO CO 3 C sodium 3 Na 0 3 David Reckhow CEE 370 L#8 3
4 Steps in Solving chemical equilibria (cont) 3. Solve the equations You should have as many independent equations as chemical species Often it is easiest to solve for and then use that concentration to calculate all other species David Reckhow CEE 370 L#8 4
5 Example 4. Determine the species present if the following compounds are dissolved into water, in both open and closed systems: a) Sodium carbonate, Na CO 3 b) Sodium bicarbonate, NaCO 3 c) Sodium phosphate, Na 3 PO 4 David Reckhow CEE 370 L#8 5
6 Solution to 4. a) First the sodium carbonate will dissolve - Na CO 3(s) Na CO3 Then the carbonate can become protonated - CO 3 - CO 3 CO (aq) CO - 3 CO (aq) 3 O CO (aq) 3 Finally, in an open system, the carbon dioxide can escape as a gas CO (aq) CO (g) David Reckhow CEE 370 L#8 6
7 Solution to 4. b) First the sodium bicarbonate will dissolve NaCO (s) 3 - CO 3 - CO 3 - Na CO3 Then the bicarbonate can become protonated or deprotonated CO (aq) CO - 3 CO (aq) 3 O CO (aq) 3 Finally, in an open system, the carbon dioxide can escape as a gas CO (aq) CO (g) David Reckhow CEE 370 L#8 7
8 Solution to 4. c) First the sodium phosphate will dissolve Na3 PO 4 3Na PO 3-4 Then the phosphate can become protonated 3- - PO PO - PO 4 4 Finally, in an open system, there are no additional species to consider, because there are no gas-phase forms of phosphate 4 PO 4 - PO PO (aq) David Reckhow CEE 370 L#8 8
9 Carbon Forms: Definitions Inorganic Carbon (IV oxidation state) CO carbon dioxide (dissolved and gas) CO 3 carbonic acid (dissolved) CO - 3 bicarbonate (dissolved) CO - 3 carbonate (dissolved) CaCO 3 calcium carbonate (mineral) Organic Carbon (< IV oxidation state) C 6 O 6 glucose (a sugar) C 3 COO acetic acid (a carboxylic acid) David Reckhow CEE 370 L#8 9
10 The Carbonate System CO (aq) O CO 3 Major buffer ions volatile: interaction with atmosphere biologically active Definitions: CO (aq) CO CO * 3 3 * CO CO CO C T David Reckhow CEE 370 L#8 0
11 Carbonate System (C T 0-3 ) C T Log C p p CO 3 CO 3 - CO p O - Log Log CO3 Log CO3- Log CO3- Log O- Compare with Figure -0 David Reckhow CEE 370 L#8
12 Rapid Method for Log C vs. p Graph. Plot diagonal and O - lines. Draw a light horizontal line corresponding to log C T 3. Locate System Point i.e., p p a, log C log C T make a mark 0.3 units below system point 4. Draw 45º lines (slope ±) below log C T line, and aimed at system point 5. pproximate curved sections of species lines ± p unit around system point 6. Repeat steps as necessary for more complex graphs #3-#5 for additional p a s of polyprotic acids #-#5 for other acid/base pairs David Reckhow CEE 370 L#8
13 David Reckhow CEE 370 L#8 3 T T T C C C Diprotic acids: calculations Start with C T and a equations C T
14 David Reckhow CEE 370 L#8 4 Diprotic acids: calculations (cont.) Use /C T and a equations to get other α s α 0 For distribution diagrams Note: α 0 α α C T T T T C C C T T T C C C α α
15 Diprotic acids: calculations (cont.) α 0 C T α C T α C T If p << p, or >> / / If p << p << p, or >> >> / / If p,<< p, or >> / / David Reckhow CEE 370 L#8 5
16 Substances of low solubility Solubility product defines the limit of solubility For calcium sulfate we have: so Ca SO David Reckhow CEE 370 L#8 6
17 Solubility Solubility product constants The solubility product constant for the dissolution of CaSO4 is about If you add 00 g of CaSO4 (GFW36) to liter of water, what will the calcium concentration be? so Ca Ca Ca 0 0 SO M 4 0 If you have a solution of 0 - M NaSO4 which is entirely dissolved, and to this you add an excess of CaSO 4 crystals, how much of the calcium sulfate will dissolve at equilibrium. Present your answer in moles per liter 4.6 David Reckhow CEE 370 L#8 7
18 Organic Chemistry Definitions & Intro Properties and Nomenclature lkanes lkenes lkynes licyclics romatics Functional Groups David Reckhow CEE 370 L#8 8
19 Nomenclature: Intro Carbon can form a nearly limitless diversity of compounds. One reason for this is carbon's ability to bind covalently with itself in long chains: C C C C C C C C In the above structure, each carbon atom (C) is surrounded by four single bonds. This is a consequence of carbon's tendency to form four covalent bonds each. These extra bonds not used to join the carbon chain may be linked to hydrogen atoms or other structures. The particular structure shown above is an aliphatic chain. The carbons are linked in a linear fashion, without forming rings or cycles. David Reckhow CEE 370 L#8 9
20 Nomenclature: lkanes. Unbranched lkanes n homologous series of simple aliphatic organic compounds is then the following: C C C C C C C C C C C C C C C Methane Ethane Propane Butane Pentane The series continues: hexane (6C), heptane (7C), octane (8C), nonane (9C), decane (0C), etc.. ll alkanes have the general empirical formula, C n n. David Reckhow CEE 370 L#8 0
21 Nomenclature: Branched lkanes. Branched lkanes & IUPC Nomenclature The smallest branched aliphatic is called Isobutane because it is an isomer of butane (often referred to n-butane to distinguish it from isobutane). n isomer is a compound with an empirical formula identical to a second compound, but with a different structure (i.e., geometric arrangement of the atoms) is different. C C C C Shorthand version David Reckhow CEE 370 L#8
22 Nomenclature: Position n-eptane -Methylhexane 3-Methylhexane 3-Methylhexane -Methylhexane David Reckhow CEE 370 L#8
23 Nomenclature: lkenes 3. lkenes If one were to remove two hydrogens from each of the alkanes, leaving a carbon-carbon double bond in their place, one would have the series known as alkenes or olefins. Organic compounds such as these having double or triple bonds are often referred to as unsaturated, because they have less than the maximum possible number of hydrogens. Ethene Propene -Butene -Butene -Pentene -Pentene David Reckhow CEE 370 L#8 3
24 Nomenclature: lkynes 4. lkynes Removal of 4 hydrogens from two adjoining carbons in an alkane results in the formation of a carbon-carbon triple bond. The homologous series of these compounds is termed the alkynes (suffix -yne) and has the general empirical formula, C n n-. Ethyne Propyne -Butyne -Butyne -Pentyne -Pentyne David Reckhow CEE 370 L#8 4
25 Nomeclature: licyclics 5. licyclic ydrocarbons When hydrocarbon chains are joined to make a ring, they are said to be cyclic, or more properly, alicyclic. They may also have double and triple bonds (e.g., cycloalkenes, cycloalkynes, in addition to cycloalkanes). licyclic compounds are often given the prefix, "cyclo". These compounds have the general empirical formula, C n n. Cyclopentane Cyclohexane David Reckhow CEE 370 L#8 5
26 Nomenclature: romatics 6. romatics Six-membered rings containing three alternating double and single bonds are given a special name, aromatic. These compounds are especially stable. The simplest aromatic compound is benzene. David Reckhow CEE 370 L#8 6
27 romatics ekulé resonance structures of benzene Polynuclear (or Polycyclic) romatic ydrocarbons (Ps) Naphthalene nthracine Pyrene David Reckhow CEE 370 L#8 7
28 Nomenclature: Funct. Groups Name Structure Suffix/Prefix lcohols C O cids C O C O O O -ol -oic acid -ate etones C O -one ldehydes C O -al mines C N -yl amine David Reckhow CEE 370 L#8 8
29 Nomenclature: Funct. Groups Name Structure Prefix/Suffix Esters C O R lkyl(r) -at Ethers C O C alides C Cl chloride C Br bromide mide C O N Nitriles C N -nitrile O David Reckhow CEE 370 L#8 9
30 Nomenclature question # What is this called?. Chloromethane B. Chlorobenzene C. Chlorobenzoic acid D. Chlorohydroxyethane E. None of the above David Reckhow CEE 370 L#8 30
31 Nomenclature question # What is this called?. -propanoate B.,4-hydroxbutamine C. Pentane-3-al D.,5-hydroxybutamine E. 4-amino--pentanol David Reckhow CEE 370 L#8 3
32 Nomenclature question # What is this called?. Chloromethane B. Chlorobenzene C. Chlorobenzoic acid D. Chlorohydroxyethane E. None of the above David Reckhow CEE 370 L#8 3
33 Nomenclature question #3 What is this called?. -Chlorobenzoic acid B. -Chlorobenzoic acid C. 3-Chlorobenzoic acid D. 4-Chlorobenzoic acid E. 5-Chlorobenzoic acid David Reckhow CEE 370 L#8 33
34 To next lecture David Reckhow CEE 370 L#8 34
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