CHE 102 Study Guide - Midterm Guide: Acyl Halide, Acetic Acid, Anomer

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8 Feb 2017

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Structure of a Carboxylic Acid
Structure of an Ester
Structure of an Amide
Structure of an Acid Halide
Structure of an Acid Anhydride
Synthesis of Carbon is prepared by
limited oxidation of primary alcohols
Naming Carboxylic Acids
1. Find longest chain containing -COOH group
2. Drop the -e from the end of the alkane name and substitute "-oic acid"
3. Number and name the branches or other substituents
* #1 Carbon is the acid carbon (carbonyl carbon)
Physical Properties of Carboxylic Acids
presence of two polar groups results in very strong hydrogen bonding
Acidity of Carboxylic Acids
-weak acids and undergo ionization in water to form a carboxylate salt
-strength of acid is measured by the acid dissociation constant (Ka) -- the smaller the
value of Ka, the weaker the acid (opp. of how pH works)
*many carboxylic acids have about the same acid strength as acetic acid
Acetic Acid
primary organic component of vinegar
-in concentrations over 50% it is corrosive and can damage the skin,eyes, nose, and
Citric Acid
produced by almost all plants and animals during metabolism
-Lemon juice and orange juice (CITRUS) contains small percentages of citric acid,
hence the term of the fruit
-pure citric acid is white, crystalline acid that is very soluble in water
Carboxylate Salts
product of a reaction between a carboxylic acid and a strong base
Naming Carboxylate Salts
1. positive ion is named first
2. carboxylate ion is named by changing the ending of the acid's name from -ic to -ate
-OH of a carboxylic acid group is replaced with an -OR group
-Name the R group in -OR like a side chain
-Then name acid portion with -ate ending
the reaction of a carboxylic acid with an alcohol
Hydrolysis of Esters
Acid catalyzed reversal of esterification
Base Hydrolysis with a strong base
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-Salicylic Acid Derivative
--->white crystalline solid composed of acetylsalicylic acid, an ester formed between
acetic acid and the alcohol OH group of salicylic acid
-Prodrug: administered in inactive form and metabolized in intestine into the active form
-provides pain relief, reduces fever, and reduces inflammation
-undesirable side effects are gastric bleeding and gastrointestinal distress
-A Carboxylic Acid
-(Advil, Motrin) is a non-steroidal anti-inflamatory drug (NSAID) used for relief of
symptoms of arthritis, abdominal cramps, fever, and as an analgesic
-lowest incidence of adverse gastrointestinal side effects of all NSAIDs
Acid Halides
-OH of a carboxylic acid is replaced with a halide- fluoride, chloride, bromide, iodide
name by changing the end of the acid name from "-ic acid" to -oyl followed by the name
of the halide
Acid Anhydrides
formed by the combination of two acids and the loss of water
nomenclature: simplest-- halves are from the same acid
-name by changing the acid ending to anhydride
"propanoic acid--> propanoic anhydride"
amine derivative of a carboxylic acid
primary, secondary, tertiary
Physical properties of Amides
-(primary & secondary) generally have higher boiling point than similar carboxylic acids
-have generally higher water solubility
-boiling points decrease as the order of amide substitution increases
----primary > secondary > tertiary
primary and secondary amides can H bond to each other
Hydrolysis of an Amide
(addition of water) results in the formation of a carboxylic ion and amide
Tylenol- is an amide
-reduces fever and pain but is NOT an anti-inflammatory agent
-advantage- it doesn't induce internal bleeding
-pain reliever of choice for people phones to bleeding or recovering from surgery or
polyamides produced by reaction of diamines with diacids
made from diacids and dialcohols
-biomolecules containing many hydroxyl groups on adjacent carbons together with an
aldehyde or ketone group
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