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Transcript
Review for Exam 2 Introduction to Organic and Biological Chemistry Fall 2016 Chapter 12: Unsaturated Hydrocarbons 1. Know what an aromatic compound is and the bond angles found there 2. Know how to name aromatic compounds by IUPAC rules. 3. Know the physical properties of aromatics that we discussed 4. Know the chemical properties of aromatic compounds and be able to finish reactions of the following type: a. halogenation b. nitration c. sulfonation d. alkylation e. oxidation of alkylbenzenes Chapter 13. Alcohols, Phenols, Ethers and their Sulfur Analogues. 1.Know what a functional group is, especially the ones in the chapter 2. Know about the bonding, hybridization, geometry and bond angles for an alcohol 3. Be able to recognize primary, secondary, and tertiary alcohols 4. Be able to name alcohols 5. Understand why alcohols have higher boiling points and better water-solubility than corresponding alkanes. 6. Know about the chemical reactivity of alcohols a. Know that alcohols are neutral in water, but can react with strong acid b. Dehydration in sulfuric acid and high heat (180°) to give double bonds . Be able to show the major products here. c. Reaction in sulfuric acid at low heat (140°) to give a symmetrical ether (for primary alcohols only). d. Combustion e. Oxidation with chromic acid or KMnO4. A primary alcohol goes to aldehyde and secondary goes to ketone. Tertiary does not oxidize. 7. Know about the structure of phenols. 8. Be able to name phenols 9. Phenols are more soluble in water than alcohols because they are more polar. Know about the chemical reactivity a. Phenols are acidic in water (carbolic acid) b. Be able to finish aromatic reactions with phenols. (They do not act like alcohols in reactions.) c. Phenols can be oxidized (with O2) to give ketones (hydroxyl quinone to quinone) and those can be reduced (H2/Pt) to give the phenol...but only if there are other groups attached to the ring. Remember our discussion of BHT and other antioxidants. 10. Be able to recognize and name ethers 11. Understand why ethers have similar solubility in water to alcohols, but have much lower boiling points. 12. Ethers are combustible and used to be used as anesthetics. 13. Be able to recognize and name thiols 14. Know that their odor is disagreeable (think skunk spray ) 15. Know the chemical properties of thiols a. Oxidation of thiols b. Reduction of thiols c. Reaction of thiols with heavy metals like lead or mercury. Chapter 14. Aldehydes and Ketones 1. Be able to recognize and name aldehydes and ketones 2. Know that aldehydes and ketones are functional isomers (constitutional isomers that involve having different functional groups) 3. Understand why aldehydes and ketones have lower bps than alcohols, but about the same solubility in water as alcohols. 4. Know the chemical properties of aldehydes and ketones a. Oxidation with chromic acid, Benedict’s/Fehling’s, or Tollens- aldehydes oxidize to carboxylic acids, ketones cannot be oxidized. (Benidict’s/Fehlings works best with an α-hydroxy aldehyde and will also oxidize an α-hydroxy ketone, as we will see later in the semester) . b. Reduction with H2/Pt, sodium borohydride (NaBH4 )or lithium aluminum hydride (LiAlH4) or NAD+- aldehydes reduce to primary alcohols and ketones to secondary alcohols. c. Hemiacetal and full acetal formation- aldehydes and ketones react with alcohols in the presence of an acid to form hemiacetals (hemiketals) with one mole of alcohol and a full acetal (ketal) with two moles of alcohol. Chapter 15. Carboxylic acids, Esters, and other Acid Derivatives. 1. Know how to recognize and name carboxylic acids 2. Know that carboxylic acids have higher boiling points than corresponding alcohols because they can hydrogen bond more (form dimers), but have similar solubility in water. 3. Their odor is disagreeable. 4. Chemical reactivity of carboxylic acids a. Carboxylic acids are weak acids and will have a low pH in water. Understand why that is. b. Know how to make esters from carboxylic acids and alcohols in the presence of acid including polyesters. 5. Know how to recognize and name carboxylate salts 6. Know that carboxylate salts are solids at RT with high mp and bp because they are ionic compounds. 7. They are weak bases, preservatives and soaps. Know how soaps clean, what soap scum is and how to clean it/ avoid it. 8. Be able to recognize and name esters 9. Know that esters will have lower boiling points than corresponding ketones and aldehydes, but will have similar water-solubility 10. Esters smell good; usually fruity or minty 11. Know how to hydrolyze esters in acid and in base. 12. Recognize acid halides and acid anhydrides and be able to name them 13. Know how they are used in the lab to make esters