Carboxyic Acids and Esters

R-C-(=O)- OH

• 1.carbonxyl
• 2.hydroxyl

• Low molecular weights are liquids at room temp C₁----C₄
• C₁₂---C₂₀ are solids and are called fatty acids
• The acids are usually associated w/ an unpleasant aroma (sweat, sauerkraut)

• 1. carboxyic acids
• 2.alcohols
• 3.aldehydes and ketones
• 4.alkenes and ethers

• Short chain acids are very soluble in water
• They can form hydrogen bonds b/w the carboxyl group (or hydroxyl) and water
• More than C₆ tend to be insoluble

2 identical molecules bonded together with a hydrogen bond

oxidation of ethanol or ethanal

primary alcohol+[O]-->aldehyde+[O]-->carboxylic acid

• Find the longest carbon chain containing the COOH group
• -the carboxyl carbon is #1 (so no numbering needed)
• Drop -e from the alkane add -oic acid
• Number and name any branches or substituents

• 1. Carbocylic acid
• 2. Aldehyde
• 3. Ketone
• 4. Alcohol
• 5. Amine
• 6. Alkene= Alkyne
• 7. Alkane
• 8. Ether

• Oxalic acid
• simplest dicarboxylic acid
• found in spinach, rhubarb, and cabbage

lactic acid

sordic acid

• glycolic acid
• <10% in skin care products

citric acid

salicylic acid

the most important property of the acids is there acidic behavor. carboxylic acids behae as weak acids. the general reaction w/ water followes (see notes)

ex. propionic acid + sodium hydroxide-> sodium proanoate + water

acid+hydroxide---> salt+water

• the positive ion is named first, followed by a serparate word giving the name of the negitive ion
• drop -e and add -oate

react thw salt w/ a solution of a strong acid such as hydrochloric or sulfric

salt + strong acid---> acid + salt

• their solubility is much greater in water than that of the acid they are derived from
• (benzoic acid 3.4g/L)(Na benzoate 550 g/L)
• drugs and meds that contain acid groups are usu. marketed as Na & K salt. this greatly enhances the wase of absorption by the body

acetic acid+ strong base--> salt + water

R-C(=O)-Cl

CH₃C(=O)OH--PCl₃-->CH₃C(=O)Cl

drop -e and add -oyl and add chloride to the end

R-C-(=O)-O-C-(=O)-R

formed from the combination of 2 acids and the loss of water

splitting with the addition of water

almost done =)

• neutralization
• acid+base--->salt+water
• Note: the name of the cation came from the base is nameed first in the salt

R-C(=O)-O-R

• cannot form H+ bonds w/ one another b/c they lack a H+ bonded to the O atom
• the BP's are much lower than those of alcohols & acids of comparable molecular mass
• water molecules can form H bonds to esters through the O atom present in the ester functional group. B/c of this, low molecular weight esteres are water soluble

carboxylic acid+alcohol---> ester+water

R-C(=O)-OH+ ROH--->R-C(=O)-O-R+H₂O

• OH of the acid is replaced w/ the OR from the alcohol
• -Name the R group like a side chain
• -Then name the acid portion w/ -oate ending

acid chloride+alcohol-->ester+ hydrogen chloride

R-C-(=O)-Cl+R-OH---> R-C-(=O)-OR+HCl

acid anhydride+alcohol--->ester+ carboxylic acid

ester+water--->acid+alcohol

salicylic acid+acetic anhydride--->acetylsalicylic acid (ASH)+ acetic acid

(equation in notes)

glycerol+nitric acid--->nitroglycerin+water

esters of phosphoric acid are found in living organisms

ALL DONE!!! =)