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Biochemistry

Biochemistry. Chapter 10 Intro to Organic Chemistry. Problem Sets. PS#1 Chapter 10 questions 14, 15, 16, 21, 22, 25, 27, 29, 40, 43, 49, 50 PS#2 Formulas and nomenclature Ch 11: 23, 24 Ch 15: 16 Ch 12: 16, 18 Ch 17: 15, 16, 17 Ch 13: 12, 13 Ch 18: 5, 8 Ch 14: 11, 12.

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Biochemistry

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  1. Biochemistry Chapter 10 Intro to Organic Chemistry

  2. Problem Sets • PS#1 • Chapter 10 questions • 14, 15, 16, 21, 22, 25, 27, 29, 40, 43, 49, 50 • PS#2 • Formulas and nomenclature • Ch 11: 23, 24 Ch 15: 16 • Ch 12: 16, 18 Ch 17: 15, 16, 17 • Ch 13: 12, 13 Ch 18: 5, 8 • Ch 14: 11, 12

  3. 10.1 – 10.2 Introduction • Organic chemistry – the chemistry of carbon compounds • Carbon is very versatile • Concatenation • Isomerization • Sources of Organic Compounds • Isolated from nature • Laboratory synthesis

  4. 10.3 Structure of Organic Compounds • H O | || H – C – C – O – H | H • Consider in terms of • Lewis structure • VSEPR • Hybridization

  5. 10.3 Structure of Organic Compounds • Common bonding requirements: • C – 4 bonds • N – 3 bonds • O – 2 bonds • H – 1 bond • Halogens – 1 bond • Other atoms follow periodic trends • S bonds like O • P bonds like N

  6. 10.3½ Hydrocarbons • Contain only carbon and hydrogen • Saturated – single bonds only • Unsaturated – one or more double or triple bonds • Aliphatic Hydrocarbons • Alkanes – all single bonds • Alkenes – at least one double bond • Alkynes – at least one triple bond • Aromatic Hydrocarbons • Benzene and its derivatives

  7. 10.3½ Representing Hydrocarbons • Lewis Structures • Ball and Stick Diagrams • Line Angle Formulas

  8. 10.4 Functional Groups • An atom or group of atoms attached to an organic compound with a characteristic set of properties • Often sites of chemical reactions • Determine properties of compound • Used to classify compounds • Primary (1o) Secondary (2o), Tertiary (3o)

  9. 10.4 Functional Groups Carboxylic Acids R–OH Alcohols R–O–R Ethers R–NH2 Amines Aldehydes Ketones Esters

  10. 10.4½ IUPAC Nomenclature • Official rules for naming • Common names are often used • Name based on longest unbranched chain • 1 C meth- 6 C hex- • 2 C eth- 7 C hept- • 3 C prop- 8 C oct- • 4 C but- 9 C non- • 5 C pent- 10 C dec- • Prefix rings with cyclo-

  11. 10.4½ IUPAC Nomenclature • Ending based on functional group • Alkane -ane • Alkene -ene • Alkyne -yne • Alcohol -ol * • Amines -amine * • Aldehyde -al * • Ketone -one * • Carboxylic acid -oic acid * • Name hydrocarbon, then replace final -e

  12. 10.4½ IUPAC Nomenclature • Use numbers to locate functional groups • Number so that functional group (or double bond) has lowest value • Branched chains • Name side chain by length, add –yl ending • List side groups in alphabetical order • Use numbers to indicate where side chain lies • Number so that first side chain has the lowest # • Use prefixes (di-, tri-, etc.) for multiple side chains • sec- and tert- for branched side groups

  13. 10.4½ Nomenclature for Arenes • Name ring substituents as normal • Number multiple substituents • Ortho-, meta-, and para- • Common names • f – OH phenol • f – CH3 toluene • f – CH=CH2 styrene • f – COOH benzoic acid • Benzene side group is called phenyl-

  14. 10.4½ Name These CH3CH2CH2CH2CH2CH3 | CH3 Cl Cl | | CH3-CH-CH2-CH-CH2-CH3 2-methylhexane 2,4-dichlorohexane Cl | CH3CH2CH2OH m-dichlorobenzene or 1,3-dichlorobenzene 1-propanol Cl CH3CH=CHCH2CH3 O || – CH2–CH2–C–H 2-pentene 3-phenylpropanal

  15. 10.4½ Name These butane 2-methylbutane cyclopentane methylcyclohexane

  16. 10.4¾ Isomerism • Compounds with the same molecular formula but different structural formula • Constitutional Isomers • Chains attached in a different order • Eg: CH3CH2CH2CH3 versus CH(CH3)3 • Try drawing 5 different isomers for C6H14 • Functional Isomers • Different functional groups • Eg: CH3CH2OH versus CH3-O-CH3

  17. 10.4¾ Stereoisomerism • Cis-Trans Isomerism • Substituent groups have different arrangement in space • Applies to alkenes and some rings • Cis – same side • Trans – opposite sides • Prefix name with cis- or trans-

  18. 10.4¾ Stereoisomerism Name the following isomers: 1-butene cis-2-butene trans-2-butene methylpropene

  19. 10.4¾ Stereoisomerism • Enantiomerism • Isomers that are mirror images • Chirality (“handedness” of molecule) • Other stereoisomers are called achiral • Racemic mixture • Equal amounts of each enantiomer • Detected by rotation of polarized light • Dextro- (right), Levo- (left)

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