CHAPTER 19: CARBOXYLIC ACIDS GENERAL INFO · 2018. 1. 19. · Page 5 ANTIOXIDANTS Reaction of oils...
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Page 1 C HAPTER 19: C ARBOXYLIC A CIDS GENERAL INFO EXAMPLES OF CARBOXYLIC ACIDS Formic acid Stinging ants Acetic acid Vinegar (5%) Butyric acid Smell of rancid butter Also in parmesan cheese and vomit Isovaleric acid Main component of foot odor Caproic Acid Smell of goat and barnyard animals One of the components in body odor Oxalic acid Found in spinach Kidney stones are calciumoxalate Citric acid Found in citrus, and is a metabolite NOMENCLATURE 1. The C=O is understood to be carbon #1. Ending is –oic acid.
Transcript of CHAPTER 19: CARBOXYLIC ACIDS GENERAL INFO · 2018. 1. 19. · Page 5 ANTIOXIDANTS Reaction of oils...
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CHAPTER 19: CARBOXYLIC ACIDS
GENERAL INFO
EXAMPLES OF CARBOXYLIC ACIDS
Formic acid Stinging ants
Acetic acid Vinegar (5%)
Butyric acid Smell of rancid butter
Also in parmesan cheese and vomit
Isovaleric acid Main component of foot odor
Caproic Acid Smell of goat and barnyard animals
One of the components in body odor
Oxalic acid Found in spinach Kidney stones are
calciumoxalate
Citric acid Found in citrus, and is a
metabolite
NOMENCLATURE 1. The C=O is understood to be carbon #1. Ending is –oic acid.
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2. All other groups are substituents. The CO2H is the highest priority group.
3. Alkenes/ alkynes are –enoic acid and –ynoic acid.
SPECTROSCOPY
IR SPECTRA
1H NMR SPECTRA
OH
O
OH
O
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ACIDITY
WHY ARE CARBOXYLIC ACIDS ACIDIC? Carboxylic Acids are the only mainstream functional group that produce a noticeably acidic aqueous solution, which can be verified by litmus paper.
CH3OH + H2O
Alcohol Carboxylic Acid
Salicylic Acid Skin care and wart remover
Glycolic Acid An “alpha-hydroxy acid”
In skin care
Lactic Acid Cause of sore muscles
ACIDITY TRENDS
ADDITION OF ELECTRON-WITHDRAWING GROUPS (EWG)
pKa1
1 Solomons, G., Fryhle, C.B., Organic Chemistry, 8th ed., Wiley, 2004, pp. 817.
O
O
H + H2O
HO
O
HO
O
Cl HO
O
Cl
Cl
HO
O
Cl
ClCl
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PROXIMITY OF EWG
pKa2
RESONANCE CONSIDERATIONS
pKa
CARBOXYLIC ACIDS VS. PHENOLS
CH3OH
pKa 18 5
2 Smith, M.B., March, J., March’s Advanced Organic Chemistry, 5th ed., Wiley, 2001, pp.343.
HO
O
ClHO
O Cl
HO
O
Cl
OH
O
H3CO
OH
O
OH
O
O2N
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ANTIOXIDANTS Reaction of oils (fats) with free radicals in the body:
Radical Scavengers:
BHT is indefinitely stable.3
RELEVANT REACTIONS
ACID-BASE REACTIONS
REACTION WITH STRONG BASE (NaOH)
3 Carey, F.A., Sundberg, R.J., Advanced Organic Chemistry, 4th ed., Kluwer Academic/Plenum Publishing, 2000, pp. 666.
(free radicals in body)
Vitamin E
Butylated hydroxy toluene, (BHT), food preservative
OH
ResveratrolFound in skin of red grapes
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REACTION WITH WEAK BASE (NaHCO3)
SYNTHESIS VIA OXIDATION
JONES OXIDATION
BENZYLIC OXIDATION
OH
O NaHCO3
OH
NaHCO3
OH
OH
O
KHCO3
Girl making a vinegar / baking soda volcano
Devise a synthesis:
