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Hydrocarbon Derivatives

Aldehydes Ketones Carboxylic Acids Esters. Hydrocarbon Derivatives. Carbonyl Group. >C  O o xygen attached to carbon by double covalent bond s trong dipole-dipole forces. O. . Al dehydes. g eneral formula: R  C  H or RCHO c arbonyl group always at end of aldehyde

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Hydrocarbon Derivatives

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  1. Aldehydes Ketones Carboxylic Acids Esters Hydrocarbon Derivatives

  2. Carbonyl Group • >CO • oxygen attached to carbon by double covalent bond • strong dipole-dipole forces

  3. O  Aldehydes • general formula: RCH or RCHO • carbonyl group alwaysat end of aldehyde • find name of alkane with same # of C’s • change the -e (in ane ending) to -al • never need #’s for aldehydes • functional group always on end C

  4. O OH =  HCH + H2 aldehydes created by dehydrogenating an alcohol HCH H

  5. HCH O  methanal O H HCCH H  ethanal common name = acetaldehyde common name = formaldehyde

  6. Acetaldehyde • carcinogenic compound • natural component of many ripe fruits • contributes to odors such as: • rosemary, daffodil, bitter orange, camphor, angelica, fennel, mustard, & peppermint • component of cigarette smoke

  7. CH3CH2CH2CHO 4 carbons so base name is butane drop -eand addal butanal CHO ending indicates aldehyde

  8. - O R H H R -  - +  C=O C=O   + + H H Properties of Aldehydes aldehydes are polar! ↑ bp over alkane with same C’s H-bonding with H2O which ↑ solubility in water

  9. O = RCR' Ketones • carbonyl group: >C=O • located onC in middle of chain instead of at end • general format: R and R‘: represent hydrocarbon chain - may or may not be the same

  10. Naming Ketones • nearly always have number • take corresponding alkane name: • drop -e (from ane ending) & add -one • # gives location of functional group: >C=O • (lowest possible #)

  11. H O H HCCCH H H = propanone common name = acetone = CH3CH2CH2CCH3 2-pentanone O

  12. Aldehydes & Ketones • known for appealing tastes & smells • used as flavorings in food & candy • used as fragrances in perfumes • vanilla & cinnamon are aldehydes

  13. Properties of Aldehydes & Ketones • aldehydes & ketones: • contain C=O group • molecules polar (soluble in water) • boiling point: • higher than alkanes (same # C’s) • lower than alcohols (same # C’s)

  14. O Acidic H+ = Carboxylic Acids • general formula: RCOH • contains: carbonyl group AND hydroxyl group bonded to same C • H is acidic; so ionizes in water! • carboxylic acids are electrolytes!

  15. Ionization of Acetic Acid CH3COOH(l) + H2O(l)  CH3COO-1(aq)+ H3O+1(aq)

  16. O = Carboxylic Acids • general format: R-C-OH or R-COOH

  17. alcohol aldehyde ketone Which of the following is an electrolyte? • CH3OH • CH3COOH • CH2O • C3H6O correct answer is B (carboxylic acid)

  18. Correct answer is D (alcohol) Which of the following is a non-electrolyte? • HCl • CH3COOH • NaOH • CH3OH

  19. Naming Carboxylic Acids • never needs number: • functional group always at end • find name corresponding hydrocarbon • drop -e (from ane ending) & add -oic + acid

  20. O 1 C  methane methanoic acid sting from red ants, bees H HCCOH H = ethanoic acid acetic acid 2 C  ethane = HCOH O

  21. CH3CH2CH2CH2COOH 5 C’s  pentane so the name ispentanoic acid

  22. Common carboxylic acids • acetic acid – vinegar • produced in doughs leavened with specific yeast (ex: sourdough bread) • citric acid • tannic acid • ascorbic acid • lactic acid • produced in overworked muscles & causes pain • poly(lactic acid) – biodegradable polymers used as sutures in internal surgery

  23. Properties of Carboxylic Acids • contain -COOH group • H bonded to O therefore hydrogen bonding • bp ↑ over corresponding alkane • form H bonds with water so smaller acids are very soluble in water

  24. O = Esters • general format: RCOR‘ • R and R‘ = hydrocarbon branches • can be same or different • esters contain carbonyl group and an O bridge • both in middle of chain • esters are POLAR • no H-bonding

  25. O = Esters • RCOR‘ or RCOOR’ combination of carboxylic acid & alcohol: • carbonyl group &“R” come from carboxylic acid • bridging O & R’ come from alcohol

  26. Esters • responsible for many distinctive odors • pineapple • banana • orange • apple • wintergreen

  27. Naming Esters • name hydrocarbon branch bonded to O bridge first • branches end in –yl • base name derived from branch containing carbonyl group • count up all C’s in this branch including the C in the carbonyl • find the hydrocarbon base name • drop the -e (from ane ending) & add -oate

  28. O = CH3CH2C─O─CH3 bridge O methyl propanoate name this branch 1st carbonyl group

  29. bridge O O = CH3CH2CH2COCH2CH3 name this branch 1st ethyl butanoate pineapple

  30. bridge O O = CH3COCH2CH2CH2CH2CH3 name this branch 1st pentyl ethanoate banana

  31. O = CH3OCCH2CH2CH3 bridge O name this branch 1st 4 C’s on the other side: but methyl butanoate apple

  32. O = CH3CH2CH2CH2CH2CH2CH2CH2-O-C-CH3 bridge O name this branch 1st 2 C’s on the other side: eth octyl ethanoate orange

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