chapter 14

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Derivatives of Water. Alcohols, ROHEthers, ROR'Thiols, RSH. Nomenclature. . 0. . . 0. Classification by Carbon Degree. Methyl alcohol = primary alcoholEthyl alcohol = primary alcoholn-propyl alcohol = primary alcoholisopropyl alcohol = secondary alcohol. 0. . n-butyl alcohol = primary alcoholsec-butyl alcohol = secondary alcoholisobutyl alcohol = primary alcoholtert-butyl alcohol = tertiary alcohol.

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chapter 14

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1. Chapter 14 Alcohols, Ethers and Thiols

3. Nomenclature

5. Classification by Carbon Degree Methyl alcohol = primary alcohol Ethyl alcohol = primary alcohol n-propyl alcohol = primary alcohol isopropyl alcohol = secondary alcohol

6. n-butyl alcohol = primary alcohol sec-butyl alcohol = secondary alcohol isobutyl alcohol = primary alcohol tert-butyl alcohol = tertiary alcohol

7. Common Alcohols Methyl alcohol – wood alcohol metabolism produces formaldehyde causes blindness used as fuel in racing cars (dangerous, invisible flames)

8. Common Alcohols Ethyl alcohol – grain alcohol distillation to produce > 10 – 12 % Isopropyl alcohol – rubbing alcohol Ethylene glycol – antifreeze hazard to pets Glycerol (glycerine) – backbone of lipids

9. Physical Properties R-OH Capable of hydrogen bonding Higher bp than comparable MW alkanes More soluble than comparable MW alkanes polar = soluble to C4 C to O ratio < 4:1 means soluble diols are more soluble triols are even more soluble glucose has 5 OH groups

10. Question Which has the higher boiling point? 1-propanol or butane

11. Chemical Properties 1. Combustion alcohol + O2 ? CO2 + H2O

12. 2. Elimination (dehydration) alcohol ? alkene + water Tsayseff’s rule: “the poor get poorer” 2-butanol ? 2-butene + H2O

13. 3. Oxidation Reduction Reactions Definitions: oxidation = gain of oxygen or loss of hydrogen reduction = gain of hydrogen or loss of oxygen

14. Primary alcohol ethyl alcohol ? acetaldehyde ? acetic acid

15. Secondary alcohol isopropyl alcohol ? acetone

16. Tertiary alcohol tert-butyl alcohol ? no reaction

17. Examples [O] = oxidation [H] = reduction

18. Acidity of alcohols and phenols CH3OH + HCl ? NR CH3OH + NaOH ? NR (must have base stronger than –OH) Phenol + NaOH ? phenylate ion + Na+ + H2O

19. Ethers – Nomenclature Name alkyl groups alphabetically dimethyl ether diethyl ether isobutyl sec-butyl ether

20. Physical Properties No hydrogen bonding lower bp than alcohols less soluble than alcohols Boiling points alkanes < ethers < alcohols Solubility alkanes < ethers < alcohols <diols < triols

21. Chemical Properties Combustion Peroxide formation R-O-R’ can be oxidized to R-O-O-R’ R-O-O-R’ can be reduced to R-O-R’ H-O-O-H = hydrogen peroxide

22. Thiols – Nomenclature CH3SH methyl mercaptan methanethiol CH3CH2SH ethyl mercaptan ethanethiol

23. Physical Properties Characteristic odors skunk onion

24. Chemical Properties Redox Thiols can be oxidized to disulfides 2R-SH ? R-S-S-R Disulfides can be reduced to thiols R-S-S-R ? 2R-SH

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