B MCAT- Chem Flashcards
3 elements that can form H-bonds
Oxygen
Nitrogen
Fluorine
(Chlorine)
protecting a carbonyl
Use a vicinal diol (OH-C-C-OH) forms an acetal to protect a carbonyl (aldehyde, keytone). Acidic conditions will reform the carbonyl.
Mesylates and tosylates
Sulfur in the mesylate or tosylate (aromatic ring attached) bond with the oxygen of an alcohol to turn an alcohol into a good leaving group.
protecting an alcohol
Acetic anhydride or tosyl chloride can be used to protect an alcohol.
amine vs. imine vs. amide
An amine is carbon with a single bond to oxygen.
An imine is a carbon with a double bond to oxygen.
An amide is a carbonyl C bound to a N as well.
strong oxidizing agents
Strong oxidizing agents can take a primary alcohol and oxidize it fully to a carboxylic acid. All oxidizing agents can take a secondary alcohol to a keytone.
KMnO4 + heat
Jones reagent
Na2Cr2O7
H2CrO4
Look for oxygen-rich species with metal.
weak reducing agents
Sodium borohydride NaBH4
Weak reducing agents do one step of reduction, vs. fully reducing.
Won’t react with an ester.
Weak oxidizing agents
primary alcohol to an aldehyde
secondary alcohol to a keytone
Beware to take aromaticity into consideration though–the more stable molecule could require a strong oxidizing agent to make a change.
PCC
Strong reducing agents
LiAlH4
carboxylic acid »_space;primary alcohol
keytones»_space; secondary alcohols
esters»_space; alcohols
amides»_space; amines
Reducing agents common in breaking disulfide bonds in a lab
beta-mercaptoethanol
dithiothreitol (DTT)
It takes a reducing agent to break a disulfide bond. Requires two S-H bonds to form an S-S bond.
Two main classes of sugars, divided by their functional groups
ALDOSES–priority functional group is an aldehyde
KETOSES–priority functional group is a keytone.
hemiacetal
vs.
hemiketal
Both have an anomeric C attached to an ether, an alcohol, and a C.
In a hemiacetal, the fourth bond on the anomeric carbon is to a hydrogen.
In a hemiketal, the fourth bond on the anomeric carbon is to another carbon.
Acetal/Ketal has another ester (-OR group) in place of the alcohol.
mutarotation
opening and closing of sugar rings in aqueous solution.
Allows the anomeric carbon to rotate between the alpha and beta anomers.
Tollen’s reagent
Tollen’s reagent ONLY oxidizes aldehydes to acids. Can therefore be used to aldehydes and keytones and to identify reducing sugars.
(positive test makes silver mirror)
Benedict’s test also tests for reducing sugars.
Fehling’s Solution
?????
REDOX test specifically for sugars
pKa + pKb =
pKa + pKb = 14 (pKw)
pH + pO=H = 14
[OH][H+]=10^-14
Disassociation constant, ionization constant, equilibrium constant
All mean the same thing.
What makes an acid or base strong?
Complete disassociation in aqueous solution.
Strong acid Ka>1
Strong base Kb>1
Ka * Kb = Kw (10^-14)
Inert = less reactive than water. Negligible, too small to matter. The conj a/b of strong a/b is inert.