Bookmark Flashcards
List priority of functional groups
CAs, anhydrides, esters, amides, ald, ket, alc, amines, alkenes, alkynes, alkanes
Alkenes and alkynes = tied except in cyclic cmpds where alkenes > alkynes
All trends on periodic table
Electronegativity, ionization energy, e- affinity, electrostatic force, nonmetallic properties inc up a group and to the right of a period
Atomic radius, metallic properties, nucleophilicity inc down a group and to the left of period
Ionic radius is variable, but cations = smaller than anions of same element b/c you lost e-
Good leaving group, electrostatic forces (due to Zeff eqn), and acidity inc down and right; basicity dec down and right
Order of increasing bpt b/w alcs, alkanes and ald/ket
Alkanes < ald/ket < alcs
Mesylate and tosylate serve as protecting groups for alcs. How do they revert back to alcs?
Using a strong acid
How acidic are hydroxyl H’s?
Weakly acidic, but phenol H’s = more acidic than those of other alcs —> phenols can form salts w/ inorganic bases like NaOH. Phenols have high Ka/low pKa
Descending acidity: phenols > alkyl alcs > cyclo alcs (cyclo alcs rather donate e- instead of accepting them)
ONLY CHIRAL MOLEC = OPTICALLY ACTIVE —> can rotate plane of polarized light
Yep. OPTICAL ACTIVITY IS ONLY DETERMINED EXPERIMENTALLY, ITS NOT RELATED TO ABSOLUTE CONFIG OF MOLEC (ie. Not related to R/S or D/L)
Hemiacetals/ketals = hard to isolate and tend to continue they acetal/ketals. Why?
Hemiacetals/ketals = unstable and hydroxyl group = rapidly protonated UNDER ACIDIC CONDITIONS (IE. EXCESS IN ACID —> straight to acetals/ketals)
Remember to keep watch of nucleophilic addn vs nucleophilic subn
if a molec = added on vs if a molec replaces an old molec
Are ald more reactive to nucleophilic attacks or ket?
Ald b/c less steric hindrance compared to ket
Flow cytometry
single cells from cell cultures or tissue samples = stained by protein markers using specific ab
How does ester become alc + CA?
Hydrolysis: water attacks carbonyl and adjacent O grabs bonded water’s H, another water grabs doubled bonded OH and makes CA
Amides can be reduced to amines via? Amides can be hydrolyzed to? Describe mechanism for amide hydrolysis
LAH. Hydrolyzed to CA + amine
1) Carbonyl O = protonated —> =OH at top
2) water attacks carbonyl C of amide —> -OH at top, water at bottom
3) amino group steals H from water
4) -OH at top doubles bonds with C —> kicks out amino group, =OH at top again
5) =OH = deprotonated —> CA + amino group
Do Strecker or Gabriel synthesis produce optically active solns? Are they dehydration rxns?
no optically active solns –> racemic mixture. NEITHER = dehydration rxns
Ubiquinone
aka Coenzyme Q in ETC; can be reduced to ubiquinol. It’s a small, hydrophobic molec that can move freely in inner mito membrane
4 major factors affecting nucleophilicity. Nucleophilicity trend on periodic table. Nucs theoretically act as a?
Charge: more neg —> more nucleophilic b/c of inc e- density --> donate more e- Size: the smaller, the better b/c less sterically hindered; BUT if nuc = neutral, then bigger size --> better nuc b/c you have more e- to donate Electronegativity: less electronegativity —> better nucleophile b/c high electronegativity means that atoms = less likely to share e- density Solvent: worse in protic solvents b/c the solvent can protonate or H bond w/ the nuc —> defeats the purpose of the nuc Inc down and left Lewis base (b/c they like to donate e-)
