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-dipole forces

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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
• drop the -e (in ane ending) 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
common name acetaldehyde
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Acetaldehyde

• carcinogenic compound
• component of cigarette smoke
• natural component of many over-ripe fruits
• contributes to odors such as
• rosemary, daffodil, bitter orange, camphor,
  angelica, fennel, mustard, peppermint

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

• carbonyl group gtCO
• located on C in middle of chain instead of at
  end
• general format
• R and R represent hydrocarbon chain
• - may or may not be the same

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Naming Ketones

• nearly always have number (except 3Cs)
• take corresponding alkane name
• drop -e (from ane ending) add -one
• gives location of functional group gtCO
• (lowest possible )

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O
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Aldehydes Ketones

• known for appealing tastes smells
• flavorings in food candy
• fragrances in perfumes
• examples vanilla cinnamon

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Properties of Aldehydes Ketones

• aldehydes ketones
• contain CO group
• 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

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dissociation of acetic acid
Remember all acids dissociate in water! -
carboxylic acids are electrolytes!

• CH3COOH(l) H2O(l) ?
• CH3COO-1(aq) H1(aq)

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Carboxylic Acids

• 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 (carboxylic acid)
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Which of the following is a
non-electrolyte?

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 (from ane ending) 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
• produced in overworked muscles causes pain
• 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 bonding
• bp ? over corresponding alkane
• form H bonds with water so smaller acids are very
  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 an O bridge
• both in middle of chain

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Esters

• esters are POLAR
• due to carbonyl group O bridge
• no H-bonding
• no FON
• form as product of chemical reaction between
  organic acid and an alcohol

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Esters

• R?C?O?R or RCOOR
• reaction between carboxylic acid alcohol
• carbonyl group R come from carboxylic acid
• bridging O R come from 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 O bridge first
  
• prefix yl
• base name derived from branch containing carbonyl
  group
• count up all Cs in this branch including the C
  in the carbonyl
• hydrocarbon base name
• drop the -e (from ane ending) add -oate

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name this branch 1st
carbonyl group
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pineapple
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banana
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apple
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orange