General Chemistry II
General Chemistry II CHEM 1120
Utah State University
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Date Created: 10/28/15
Chapter 18 Amines and Amides Learning Objectives 1 Provide both IUPAC and common names for amines 2 Differentiate primary secondary and tertiary amines 3 Recognize the physical properties of amines 4 Recognize heterocyclic amines 5 Provide both IUPAC and common names for amides and write the equations for amidation from amines 6 Write the equations for the hydrolysis of amides Sections 1 8 1 Amines 182 Properties of Amines 183 Heterocyclic Amines and Alkaloids l 84 Amides 185 Hydrolysis of Amides Recommended additional problems l8411843184518481851 181 Amines A Classi cation of amines 1 i F NH3 in H try R llJ R ammonia R R R 1 amine 2 amine 3 amine R N R 4 ammonium B Nomenclature of amines NHZ NH NH2 amp JO NH2 HO NHZ NH2 0 182 Properties of Amines A Boiling points B Solubility in water C Amines react as bases D Ionization of an amine in water E Basicity of amines F Amine salts G Properties of amine salts 183 Heterocyclic Amines and Alkaloids A Heterocyclic amines O U U H B Alkaloids amines in plants 184 Amides A Preparation of amides B Nomenclature of amides O o ANHZ UN H I C Physical properties of amides 185 Hydrolysis of Amides A Acid hydrolysis of amides B Base hydrolysis of amides Chapter 20 Enzymes and Vitamins Learning Objectives 1 Describe how enzymes function as biological catalysts and name and classify them 2 Describe the effect of temperature pH concentration of enzyme and concentration of substrate on enzyme activity 3 Describe reversible and irreversible inhibition 4 Describe the role of zymo gens feedback control and allosteric enzymes in regulating enzyme activity Sections 201 Enzymes 202 Enzyme Action 203 Factors Affecting Enzyme Activity 204 Enzyme Inhibition 205 Control of Enzyme Activity 206 Enzyme Cofactors and Vitamins Recommended additional problems 2050 2053 2055 2059 2061 2063 2067 2069 2071 2073 2075 201 Enzymes Eart uncataiyzed Emt catalyzed a 3945 33 Tlmbsrlaks General Dronn r A Names and classi cation of enzymes i suf x ase ii Oxidoreductases Oxidation reduction Transferases Transfer groups of atoms Hydrolases Hydrolysis Lyases Add atomsremove atoms to or from a double bond Isomerases Rearrange atoms Ligases Use ATP to combine small molecules 202 Enzyme Action A Active site B Enzyme catalyzed reaction Enzymesubstrate ES complex E S ES gt C Lockand key and induced t models i Lockandkey Active site Lockandkey model Enzymeasuhstrate comp ex K ii Induced t Active site Induced fit mode Enzymesubstrate campiex 203 Factors Affecting Enzyme Activity A Temperature I Are most active at an optimum temperature usually 37 C in humans I Show little activity at low temperatures Lose activity at high temperatures as denaturation occurs Tlmbeltake enerax agam c and Siofogfcaf Chemistgy Oupyright f earm Education Inc publishing as Beniamln Bumm ngs B pH C Concentration of enzyme D Concentration of substrate 204 Enzyme Inhibition A Reversible inhibition B Irreversible inhibition 205 Control of Enzyme Activity A Zymo gens Zymogens proenzymes are inactive forms of enzymes Zymogens are activated when one or more peptides are removed Examples proinsulin is converted to insulin by removing a small peptide chain B Feedback control 206 Enzyme Cofactors and Vitamins A Cofactors and coenzymes vs cosubst rate B Metal ions C Vitamins Chapter 23 Metabolic Pathways and Energy Production Learning Objectives 1 Describe the oxidation of acetyl CoA in the citric acid cycle 2 Describes the electron carriers involved in electron transport 3 Describes the roles of electron carriers in electron transport 4 Describe the process of oxidative phosphorylation in ATP synthesis 5 Account the ATP produced by the complete oxidation of glucose Sections 231 The Citric Acid Cycle 232 Electron Carriers 233 Electron Transport 234 Oxidative Phosphorylation and ATP 235 ATP Energy from Glucose Recommended additional problems 2349 2353 2355 2357 2361 2365 2367 2369 2371 2373 2377 2379 2381 2385 2387 2389 231 The Citric Acid Cycle 0 O pyruvate dehydrogenase o HS COA NAD gt 3 COA C02 NADH O pyruvate Part2 Part1 Tinmanake mnergf nmmalh 39 P 3 39 mummyI r 1 A Part 1 Decarboxylation removes two carbon atoms Reactions 14 i Reaction 1 T 002 CH citrate z i s nthase c 0 0 H20 y gt o c Coz HS CoA H CH3 s CoA I CH2 CH2 acetyl CoA 002 loz oxaloacetate citate ii Reaction 2 Isomen39zation to isocitrate 002 TOZ39 002 CH2 CH2 CH2 aconitase I aconitase l H O l CH2 H20 T 2 Ho c H 002 302 002 Citfate amnith isocitrate iii Reaction 3 First oxidative decarboxylation C02 30239 co2 002 CH2 CH2 COZ CH2 isocitrate HC C02 deh dro enase j NAD Lggt H C 002 NADH gt HCH HO C H T oc 302 CO I 2 isocitrate C02 cxketoglutarate iv Reaction 4 second oxidative decarboxylation C02 c02 COZ39 CH2 ocketoglutarate CH2 H C H dehydrogenase NAD HS CoA H C H NADH 00 I I 002 oc CO2 S CoA aketoglutarate succmleoA Enzyme complex structurally similar to pyruvate dehydrogenase complex B Part 2 Reactions 58 i Reaction 5 Hydrolysis of succinyl CoA To I301 CH2 succinyl CoA synthetase HCH GDP PI H gt CH2 GTP HS CoA oc 00239 succinate S CoA succinyl CoA GTP ADP gt GDP ATP ii Reaction 6 Dehydrogenation of succinate 002 H 002 CH succinate C 2 dehydrogenase FAD gt I FADH2 CH2 c co 020 H 2 fumurate succmate iii Reaction 7 Hydration H coz 002 C fumarase Ho C H H H20 c H c H 02C H co 2 fumurate malate iv Reaction 8 Dehydrogenation forms oxaloacetate 002 002 HOCH malate C dehydrogenase NAD gt I NADH H H C H H c H coz coz malate oxaloacetate C Summary of citric acid cycle i An acetyl group bonds with oxaloacetate to form citrate ii Two decarboxylations remove two carbons as 2 C02 iii Four oxidations provide hydrogen for 3NADH and one FADHZ iv A direct phosphorylation forms GTP ATP acetylSCoA 3NAD FAD GDP Pi 2H20 gt 2 C02 3NADH 3H FADHZ HS COA GTP One turn of the citric acid cycle produces 2 002 1 GTP lATP 3 NADH 1 HS COA 1 FADH2 39 D Regulation of citric acid cycle I Pyruvafe dehydragenase A ADP V NEADH W ATP cede amp Aetivated by v inhibited by Examanimate Isooitrate dehydmgenase aKei agiufarate dehydrogenase a ADP V MMJH V Suceinyl 00A 232 Electron Carriers One molecule of glucose undergoes glycolysis oxidation to pyruvate and citric acid cycle has yields ATP Reduced coenzymes glycolysis 2 2 NADH Oxidation 2 pyruvate 2 NADH Citric acid cycle 2 acetyl CoA 2 6 NADH 2 FADE The reduced coenzymes can be used for the synthesis of more ATP Via oxidative phosphorylation A Oxidation and reduction of electron carrier oxidized redu0d reduced coenzyme electron carrier A electron carrler BHZ reduced OXidiZCd ox1dized coenzyme electron carrier AH electron carrier B B Four types of electron carrier FMN F 68 clusters Coenzyme Q and cytochromes i Flavin mononucleotide FMN FMN which contains avin ribitol and phosphate can accepts 2H 2equot to form reduced coenzyme FMNHg 2W 29 quot Vitamin 0 H30 NRng E p H36 N O V I l t u ilmm phosphate PM ii FeS clusters FeS clusters are groups of proteins containing iron ions and sul de FeS clusters accept electrons to reduce F63 to 1362 and lose electrons to reoxidize Fe2 to Fe3 Cluster With one iron 3 3925 T T E e39 gt s5 5SFequots SFei39Isa 8 S39 W M r a sFe3 s sie2 s e gt S Fi LS S Fiis s L S L 4 4 4Fe 4S cluster 3 Fe reS i a n 3 S fSFe iii Coenzyme Q Q or CoQ CoQ is a mobile electron carrier derived from quinine that can be reduced when the keto groups accept 2H and 2equot Quintana 05208 Om SEEM C3353wfi CHZGHW C matf2le 3 3M 393 W i i x We case W5 case 5 2Hquot 25 ohm an Oxidized coenzyme Q 6 Reduced coenzyme Q QHZ iv Cytochromes cyt Cytochromes cyt are proteins containing heme groups with iron ions The different cytochromes are indicated abbreviated as cyt a cyt a3 cyt b cyt c and cyt c Simpi ied skucture a cytochromes c and c1 mtlenake Genera awards wit infngfczi hsmfs y 39 r m L39 39 39 awnmug 233 Electron Transport The electron carriers are attached to the inner membrane of the mitochondrion There are four protein complexes Complex I NADH dehydrogenase Complex II Succinate dehydrogenase Complex III CoQCytochrome c reductase Complex IV Cytochrome c oxidase A Complex I NADH dehydrogenase H NADH 11 FMN X F62S Q NAD X FMNHZ Fe3s QH2 2X Overall reaction B Complex II Succinate dehydrogenase At Complex II With a lower energy level than Complex I FADH2 transfers hydrogen and electrons to coenzyme Q Q is reduced to QIIz and FAD is regenerated FADH2 Q QH2 FAD QHZ a mobile carrier transfers hydrogen to Complex III C Complex III CoQCytochrome 6 reductase Fe3s QH2 Fe3s Fe2s Q Fe2S H H QHZ 2 cyt b Fe3 gt Q 2 cyt b Fe2 2 H D Complex IV Cytochrome c oxidase H QH2 2 Fe3s 2 Fe2S 2 Fe3s 2 Fe2S 2 Fe3s 2 Fe2S 12 02 X cyt 3 cluster cyt C 1 cyt c I cyt a cyt a 3 X Q 2 Fe2S 2 Fe3s 2 Fe2S 2 Fe3s 2 Fe2S 2 Fe3s H20 2 H 2e 2H 1202 gt H20 234 Oxidative Phosphorylation and ATP A Chemiosmotic model and details in ATP synthesis i In chemiosmotic model each of the complexes in the electron transport process acts as a proton pump that pumps the proton across inner membrane of mitochondria matrix Outer membrane Innerr membrane low H Protons are pumped across the inner high H membrane of mitochondria as electrons flow through the respiratory chain Space between outer ami inner mitochondrial I wwwwwwwwwwwwwwwwwwwwwww quot1 W membrane channei 28 12W 211 Irk Inner mitm chondriat 1 membrane 39 mm H RAW mm mm 4H M Mitochondrial 3 ASP 3 matrix ii The high gradient of H has a tendency of reentering the matrix However the inner membrane is impermeable for H The only way H can return matrix is to pass through ATP synthase W W 8 H lntermembrane p space H 39 W Hquot lntermitochzondriai membrane Matrix F1 AD a A Timberlake General n39mm39r 39 39 r 3 Inc publishing as Benjamin Cumminga iii As protons ow through ATP synthase energy generated from the proton gradient is used to drive the ATP synthesis V ADquot P ADP Pi bind L ATP forms I ATP released 0 Copyright 2007 Pearson Benjamin Cummings All rights reserved In the F1 complex of ATP synthase A center subunit y is surrounded by three protein subunits loose L tight T and open 0 Energy from the proton ow through F0 turns the center subunit y The shape conformation of the three subunits changes 10 ADP and Pi enter the loose L site The center subunit turns changing the L site to a tight T conformation ATP is formed in the T site where it remains strongly bound The center subunit turns changing the T site to an open 0 site which releases the ATP B Electron transport and ATP synthesis fgh energy 2 age Emir energy quotFimharlaka 3913am agar362 md afmgicaf a haufgw Copyright ersce gunmanan inc publishing as Benjamln s umn inga ll 235 ATP Energy from Glucose The complete oxidation of glucose yields 6 02 6 H20 36 ATP Cymplas m h ttl Mitochondrtun mm A ATP from glycolysis glucosa gt 2 pyruvate 2 ATP 2 NADH 2 FADHZ i NADH cannot cross the inner membrane of mitochondria Therefore the cytoplasmic NADH must be recycled through an electron shuttle system ii By utilizing the glycerol 3 phosphate shuttle each cytoplasmic NADH produced in skeleton muscle and brain result in the formation of 2 ATP 12 NAD cytoplasmic NADH glycerol 3phosphate dehydrogenase CH20H CHZOH H Glycerol Dihydroxyacetone o CH20 3phosphate phosphate CHZO iii By utilizing the malateasparate shuttle which present in heart and liver each cytoplasmic NADH result in the formation of 3 ATP iv Overall ATP yielded from glycolysis 6 glucose gt 2 pyruvate 6 ATP B ATP from the oxidation of two pyruvates pyruvate gt acetyl CoA NADH Two pyruvates enter the oxidative phosphorylation leading to the production of 6 ATP C ATP from citric acid cycle One turn of the citric acid cycle by one acetyl CoA produces two C02 three NADH one FADHz and one ATP from GTP 3 NADH enter oxidative phosphorylation gt 9 ATP 1 FADH2 enters oxidative phosphorylation gt 2 ATP 1 GTP gt 1 ATP Subtotal of ATP 12 Total ATP produced 24 2 acetyl CoA enter the citric acid cycle 13 D ATP from the complete oxidation of glucose Metabolism reactions Location ATP yielded glycolysis cytosol 6 Pyruvate oxidation Inside mitochondria 6 Citric acid cycle Inside mitochondria 24 Total 36 Supplemental Material I Mitochondria and metabolism matrix Outer membrane Innerr membrane Outer membrane Freely permeable to small molecules and ions Inner membrane Irnpermeable to most small molecules and ions including H Contains respiratory electron carriers ATP synthase and other membrane transporters Matrix Contains pyruvate dehygrogenase complex citric acid cycle enzymes fatty acid Boxidation enzymes circulated DNA ribosomes and small molecules and ions such as ATP ADP Pi Mg2 Ca2 Kquot and soluble metabolites 14