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Alcohols  R— OH Functional Group = hydroxyl group = OH

Alcohols  R— OH Functional Group = hydroxyl group = OH. Alcohol names all end in –ol . Numbers tell which C atom the OH is attached to. Ex: 1-propanol. parent: propane molecular: C 3 H 7 OH empirical: C 3 H 8 O structural: CH 3 CH 2 CH 2 OH. H. H. H. C. C.

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Alcohols  R— OH Functional Group = hydroxyl group = OH

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  1. Alcohols  R—OH • Functional Group = hydroxyl group = OH Alcohol names all end in –ol. Numbers tell which C atom the OH is attached to. Ex: 1-propanol parent: propane molecular: C3H7OH empirical: C3H8O structural: CH3CH2CH2OH H H H C C C OH H H H H  Because it has 1 OH, it is a monohydroxy alcohol + The OH group makes alcohols polar. Alcohols dissolve in water because H2O is polar: OH - O H H +

  2. Compare:AlcoholsBases OH group:covalently attached an ion in solution electrolyte:noyes watersoluble…yesyes because…. OH is polar OH- is ion Ex. 1,2-ethanediol is a dihydroxy alcohol (two OH groups) Ex. 1,2,3-propanetriol is a trihydroxy alcohol (three OH groups) H H (aka ethylene glycol) H C H C O H O H H H H (aka glycerol) C H H C C O H O H O H

  3. ethylene glycol H H O H O H H C H C Ethylene glycol is widely used as an automotive antifreeze and a precursor to polymers. In its pure form, it is an odorless, colorless, syrupy, sweet-tasting liquid. Ethylene glycol is toxic, and ingestion can result in death.

  4. Glycerin (glycerol): --> clear, sweet tasting, oily liquid --> used to keep dried fruits and pastry fillings moist, in toothpaste, hand creams, eye and ear drops, suppositories (for laxatives, eg), and as an antifreeze Also: glycerin + nitric acid --> glycerol trinitrate aka nitroglycerin (dynamite) H2SO4 for drying

  5. Ex. ethanol (ethyl alcohol) = drug, solvent, fuel parent: ethane molecular: C2H5OH empirical: C2H6O condensed: CH3CH2OH H OH H H C H H H H H Ex. Alcohols can also be classified as: 1/ primary: OH attached to an end C as in ethanol 2/ secondary: OH is attached to a C that is directly attached to two other C atoms. At right: 2-butanol  3/ tertiary: OH is attached to a C that is directly attached to three other C atoms At right: 2-methyl, 2-propanol  C C H C H H H H H H H H H O H O H C C C C C C H H H H H

  6. Ex. For each example below, give the name. Circle if a mono-, di-, or trihydroxy and if a primary, secondary or tertiary alcohol. 1/ 3/ name: _________________ name: ________________ type: mono- di- tri- type: mono- di- tri- class: prim. sec. tert. class: prim. sec. tert. 2/ 4/ name: _________________ name: ________________ type: mono- di- tri- type: mono- di- tri- class: prim. sec. tert. class: prim. sec. tert. K K OH OH K K OH OH OH H OH OH K K OH OH K K methanol KOH H H H H H H H C C C C C C C H H H H H H C H H H H H H H H O H O H O H C C C C H C H H H H O H 2,3,4-hexanetriol 3-methyl, 2-pentanol

  7. Ethers - two C chains joined by an oxygen O “bridge” • Formula: R—O—R‘ • Name: (name R without -ane) + oxy + name of R‘ • Ex. methoxymethane aka: dimethyl ether • molecular: C2H6O • condensed: CH3OCH3 • Ex. methoxyethane aka: methyl ethyl ether • molecular: C3H8O • condensed: CH3OCH2CH3 H H H H O H H C C C C H H H H H C O H H H

  8. Ethers are common in organic chemistry and pervasive in biochemistry, as they are common linkages in carbohydrates and lignin.

  9. D. Aldehydes: When a carbonyl group (—C=O) replaces the CH2 at the end of a hydrocarbon Formula R—C—H Name: replace –e with –al Ex. methane: methanal: aka: formaldehyde molecular: CH2O structural: HCOH Ex. ethane: ethanal: aka: acetaldehyde molecular: C2H4O structural: CH3COH or: CH3 O H H H H O O H H H H C C C C C C H H H H O H H H C H H

  10. Carbonyl group: C=O Formaldehyde was the first polyatomic organic molecule detected in the interstellar medium[6] and since its initial detection has been observed in many regions of the galaxy.

  11. Carbonyl group: C=O Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants as part of their normal metabolism. It is also produced by oxidation of ethanol and is popularly believed to be a cause of hangovers.[2]

  12. E. Ketones: When a carbonyl group (—C=O) replaces a C in the interior of a hydrocarbon: Formula: R—C—R' Name: replace –e with –one Ex. propane: propanone: aka: acetone molecular: C3H6O condensed: CH3COCH3 or: CH3CCH3 Ex. Isomers: 2-pentanone and 3-pentanone: condensed: CH3CHOCH2CH2CH3 CH3CH2CHOCH2CH3 O O O O H H H H H H H H H H H H H H H C H C C C C C C C C C C C C O H H H H H H H H H H H H H H H C H C C H H H H

  13. The word ketone comes from the word: acetone Ketones are produced on massive scales in industry as solvents, polymer precursors, and pharmaceuticals.

  14. Organic Acids are formed by adding the carboxyl group • –COOH to a hydrocarbon chain. They are weak acids and • weak electrolytes, and are known as carboxylic acids • Functional group = --COOH = —C—OH • Name: replace –e with –oic acid • Ex. ethanoic acid (aka acetic acid in vinegar): • molecular: HC2H3O2 • condensed: CH3COOH • or: • CH3 H H H O C C C C—OH O O ethanoic acid: H H H ethane: C —OH H H H

  15. Ex. A fatty acid is a carboxylic acid –COOH with a long unbranched hydrocarbon chain “tail.” the acid the “fatty” tail Saturated fatty acids: -singleC-C bonds -pack closely -solids at room temp -animal “fats” Unsaturated fatty acids: -doubleC=C bonds bend up the tail -liquids at room temp -vegetable “oils”

  16. Fats and oils are triglycerides. They are formed when the alcohol glycerol combines with 3 fatty acids by condensing out water.

  17. benzoic acid --COOH Used in toothpastes, mouthwashes, cosmetics and deodorants for its antimicrobial properties

  18. ascorbic acid – Vitamin C --COOH

  19. Esters have the functional group: • General formula: • They are the result of an esterification reaction: • organic + alcohol  water + ester • acid • Ex. • Sulfuric acid (H2SO4) is used as a catalyst and as a • dehydrating agent to remove the water, which is why • this is sometimes called condensation reaction. H2SO4

  20. alcohol + acid…esterrifying! +

  21. Notice: In the general formula: Naming: The alkyl name of the alcohol is added to the acid group modified to end in –oate or -ate Esters have strong, fragrant aromas and are the cause of the odors and flavors of pineapple, banana, wintergreen and oranges. Ex. The smell of pineapples is due to ethyl butyrate ethanol + butanoic acid  water + ethyl butyrate (alcohol) (ester) this part is from the alcohol this part comes from the acid

  22. ethanol + butanoic acid  water + ethyl butyrate (alcohol) (ester) From the acid: From the alcohol: acid: alcohol:

  23. octanol + acetic acid  water + octyl acetate (alcohol) (ester) From the acid: From the alcohol: acid: alcohol:

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