Hydrocarbon Derivatives

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Hydrocarbon Derivatives

• Aldehydes, Ketones,
• Carboxylic Acids, Esters

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Carbonyl Group

• gtC?O
• Oxygen attached to carbon by double covalent bond
• Strong dipole

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Aldehydes

• General formula R?C?H or RCHO
• Carbonyl group always at end of aldehyde
• Find name of alkane with same of Cs
• change the -e to -al
• Never need s for aldehydes
• Functional group always on end C

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H?C?H H
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common name formaldehyde
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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

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CHO ending indicates aldehyde
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Properties of Aldehydes
Aldehydes are polar! ? bp over alkane with same
Cs Hydrogen bonding in H2O ? solubility in water
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Ketones

• Carbonyl group gtCO
• located within C chain instead of at end
• General Format
• R and R' may or may not be the same

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Naming Ketones

• Nearly always have number
• Take corresponding alkane name
• Drop -e add -one
• Number gives location of gtCO
• (Lowest possible )

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O
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Aldehydes Ketones

• Known for appealing tastes smells
• Used as flavorings in food candy
• Used as fragrances in perfumes
• Vanilla cinnamon aldehydes

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Properties of Aldehydes Ketones

• Aldehydes ketones
• contain CO group
• molecules polar (soluble in water)
• Boiling point
• higher than alkanes (same Cs)
• lower than alcohols (same Cs)

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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!

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Ionization of Acetic Acid

• CH3COOH(l) H2O(l) ?
• CH3COO-1(aq) H3O1(aq)

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Table R

• General Format R-C-OH
• or
• R-COOH

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Which of the following is an electrolyte?

• CH3OH
• CH3COOH
• CH2O
• C3H6O

Correct answer is B, the carboxylic acid
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Which of the following is a nonelectrolyte?

1. HCl
2. CH3COOH
3. NaOH
4. CH3OH

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Naming Carboxylic Acids

• Never needs number
• functional group always at end
• Find name corresponding hydrocarbon
• Drop -e add -oic acid

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H?C?OH
O
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5 Cs ? pentane so the name is pentanoic
acid
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Common carboxylic acids

• Acetic acid vinegar
• produced in doughs leavened with specific yeast
  
• (ex sourdough bread)
• Citric acid
• Tannic acid
• Ascorbic acid
• Lactic acid
• Poly(lactic acid) biodegradable polymers used
  as sutures in internal surgery

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Properties of Carboxylic Acids

• Contain -COOH group
• H bonded to O therefore hydrogen bonds
• Leads to ? bp over corresponding alkane
• form H bonds with water so smaller acids are
  pretty soluble in water

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Esters

• General format R?C?O?R
• R and R hydrocarbon branches
• Can be same or different
• Esters contain carbonyl group and a bridge O
• both in middle of chain
• Esters are POLAR
• No H bonded to O so no H-bonding

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Esters

• R?C?O?R or RCOOR
• Combination of carboxylic acid alcohol
• carbonyl group and R come from the carboxylic
  acid
• bridging O and the R come from the alcohol

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Esters

• Responsible for many distinctive odors
• Pineapple
• Banana
• Orange
• Apple
• Wintergreen

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Naming Esters

• Name hydrocarbon branch bonded to the bridge O
  first
• branches end in yl
• Base name derived from branch containing carbonyl
  group
• count up all Cs in this branch including the C
  in the carbonyl
• Find the hydrocarbon base name
• drop the -e and -oate

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name this branch 1st
Carbonyl Group
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