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Chapter 16 Organic Chemistry

In this chapter, we will explore basic organic concepts including nomenclature, structure, and functional groups. Chapter 16 Organic Chemistry. What Is an Organic Compound?. Organic vs Inorganic Vital Force Synthesis of urea Carbon chemistry

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Chapter 16 Organic Chemistry

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  1. In this chapter, we will explore basic organic concepts including nomenclature, structure, and functional groups. Chapter 16Organic Chemistry

  2. What Is an Organic Compound? • Organic vs Inorganic • Vital Force • Synthesis of urea • Carbon chemistry • Most naturally occurring or synthesized compounds.

  3. What Is an Organic Compound? • Carbon chemistry • C-C covalent bonds • C bonds with other nonmetals • Strong • Multiple bonds

  4. The Saturated Hydrocarbons or Alkanes • CxHy • If y = 2x+2, compound is a saturated hydrocarbon, also known as an alkane. • Tetravalent C

  5. The Saturated Hydrocarbons or Alkanes • Straight Chain • Branched Chain • Isomers • Constitutional • Others….later.

  6. Rotation Around C-C Bonds • Conformations • Eclipsed • Staggered

  7. The Nomenclature of Alkanes • Longest chain • Substituents • Number the chain. • Prefixes (di, tri, ...) • Alphabetical substituents

  8. The Unsaturated Hydrocarbons: Alkenes and Alkynes • Hydrocarbons with C=C or C C are unsaturated. • Alkene for double bond, alkyne for triple bond. • Unsaturated because they do not contain the maximum possible H per C.

  9. The Unsaturated Hydrocarbons: Alkenes and Alkynes • Nomenclature • -ane to -ene or -yne. • Number C atoms and indicate where multiple bond is located.

  10. Aromatic Hydrocarbons and Their Derivatives • Benzene, C6H6, prototypical. • Structure was a mystery for a long time. • Kekule’s solution. • Resonance structures.

  11. Aromatic Hydrocarbons and Their Derivatives • Monosubstituted benzenes • Toluene, phenol, etc. • Disubstituted benzenes • Ortho, Meta, Para

  12. The Chemistry of Petroleum Products • Natural gas (mostly methane) • Typically distributed by pipeline • Crude oil • Mixture of hydrocarbons • Thermal reforming, cracking • Catalytic reforming, cracking • Used to increase octane number.

  13. The Chemistry of Coal • Complex solid • C137H97O9NS • C240H90O4NS

  14. The Chemistry of Coal Figure 16.2

  15. The Chemistry of Coal • Large US supply • Prefer liquid fuels over solid fuels • Converted to synthetic gas • …on to methanol or other liquid fuels. • Fischer-Tropsh reaction • Liquid hydrocarbons from coal.

  16. Functional Groups • The presentation of organic reactions is organized around functional groups. • As an example, the double bond in an alkene is a functional group. • There are many others.

  17. Functional Groups Table 16.5 and Table 16.6

  18. Oxidation-Reduction Reactions • Already discussed these in Chapter 12. • Oxidation numbers discussed in Section 5.16 • Organic redox can be characterized by • Changes in oxidation numbers, or • Changes in number of H atoms present, or • Changes in number of O atoms present.

  19. Oxidation-Reduction Reactions Table 16.7

  20. Oxidation-Reduction Reactions • For example, carbon monoxide to carbon dioxide is an oxidation • …methanol to methane is a reduction.

  21. Alkyl Halides • Formed from alkane and halogen in the presence of UV light. • Chain-reaction mechanism

  22. Alkyl Halides • Chain reaction mechanism • Initiation • Propagation • Termination

  23. Alcohols and Ethers • Alcohol, ROH, is a functional group. • Names end in ol. • Also common names such as wood alcohol. • Classified as primary, secondary, or tertiary. • Are Brønsted acids.

  24. Alcohols and Ethers • Conjugate base of alcohol is alkoxide. • Alcohol related to water by replacement of one H. • Replace both Hs in water and get ether.

  25. Alcohols and Ethers • Ethers, ROR’. • Alcohols H bond, ethers do not. • Affects bp. • Affects solubility in water. • Ethers are an example of aprotic solvents.

  26. Aldehydes and Ketones • Primary Alcohol that has be dehydrogenated • CH3CH2OH → CH3COH • If alcohol is secondary, ketone results. • RC(OH)HR’ → RCOR’

  27. Aldehydes and Ketones • Nomenclature • Aldehydes named from corresponding carboxylic acid • Ending with al.

  28. Aldehydes and Ketones • Nomenclature • Ketones named with two alkyl groups plus ketone. ethyl methyl ketone

  29. Reactions at the Carbonyl Group • RR’C=O has negative end (O) and positive end (C). • Electrophiles are attracted to O. • For example, H+. • Nucleophiles are attracted to C. • For example, alkoxide.

  30. Carboxylic Acids and Carboxylate Ions • OH attached to carbonyl C makes a carboxylic acid, -COOH. • Carboxylate ion, -COO-. • Resonance structures • Names end in -oic acid. • Common names

  31. Carboxylic Acids and Carboxylate Ions Table 16.8

  32. Esters • Carboxylic acid plus alcohol produces ester plus water. • Other more efficient methods to prepare esters. • Name also includes product of strong acid and alcohol • Carboxylic acid esters are RCO2R’.

  33. Amines, Alkaloids, and Amides • Ammonia with one or more H replaced with alkyl. • Like alcohols, have primary, secondary, and tertiary. • Name has -amine at end. • Amines are bases, just like ammonia.

  34. Amines, Alkaloids, and Amides • To improve water solubility, ammonium salts prepared. • Amides are a combination of carboxylic acids and amines. • Produced via acyl chloride and amine • RCOCl + 2R’NH2 → RCONHR’+ R’NH3Cl- • Alkaloids isolated from plants…

  35. Amines, Alkaloids, and Amides Figure 16.6

  36. Alkene Stereoisomers • Already discussed constitutional isomers in section 16.2 • Another type of isomer is called stereoisomer. • cis and trans are stereoisomers. • Not all alkenes have cis and trans isomers.

  37. Alkene Stereoisomers • cis and trans not always enough to describe alkene stereoisomer. • E and Z methods more versatile. • Substituent atoms prioritized by atomic number: E and Z used to describe position of the two highest priority atoms.

  38. Stereogenic Atoms • The two C atoms in C=C when cis and trans isomers are possible are stereogenic atoms. • Other possibilities for stereogenic atoms. • The C in CHFClBr is stereogenic.

  39. Stereogenic Atoms • Any tetrahedral C with 4 different atoms attached will be stereogenic.

  40. Stereogenic Atoms • Stereoisomers may be mirror images of each other: enantiomers. • If the mirror images are not superposable, the stereoisomers are chiral. Figure 16.12

  41. Stereogenic Atoms …or they may not be mirror images of each other: diastereomers. • cis and trans isomers are diastereomers.

  42. Optical Activity • Optically active compounds • Rotate the plane of polarized light. • Specific rotation is a measure of the ability of a compound to do this.

  43. Optical Activity • Need a method for distinguishing the left handed and right handed version of a chiral center in a molecule or ion. • As before, substituents are prioritized. • R and S used to designate the two possible orientations of substituents.

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