1 / 24

chapter 14

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.

Antony
Télécharger la présentation

chapter 14

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

    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

More Related