Flashcards in Orgo Deck (44):
electron rich (lewis base)
ring structure with atoms of more than one kind
symmetric molecule, no distortion of polarized light
NH or NH2 group
N directly attached to carbonyl carbon
nitro group (electron donating or withdrawing? what type of director?)
NO2 attached, electron-withdrawing, meta-director
methyl and hydroxyl group (electron donating or withdrawing? what type of director?)
electron-donating, ortho- para director
How does # of electron withdrawing groups on phenol affect acidity?
More electron withdrawing groups attached= increased acidity
What stabilizes carbanions?
stabilized by electronegative groups or resonance with pi electrons (double bonds)
What is the order of free radical/ carbocation stability
tertiary > secondary > primary > methyl
positive charge of intermediate is adjacent to a double bond, very unstable because pi bond is perpendicular to empty orbital and double bond can't delocalize the electrons
molecule with positive and negative charges, usually from compounds with acidic AND basic functional groups; strong intermolecular forces
Which resonance structure contributes most to actual structure?
the most energetically favorable resonance structure (no separation of charge = most stable)
How does chain length affect hydrogen bonding and boiling point?
decreases H-bonding strength, increases boiling point
How does branching affect boiling point?
decreases boiling point b/c decreases intermolecular strength
When does hydrogen bonding occur?
H is bound to N, O, F in compound
How does conjugation affect heat of hydrogenation?
increased conjugation = decreased heat of hydrogenation
carboxylic acids linked with ester bond and loss of water
aromatic rings rxn mechanism
only follow electrophilic substitution reaction
carbocation, 2 steps, rearrangement is possible, affected by electronic factors, favored in polar protic solvents
no carbocation, 1 step/ 2nd order kinetics, affected by steric factors, inversion of configuration, needs nucleophile, favored in polar aprotic solvents
What is the order of best leaving groups in Halogens?
I > Br > Cl > F
equal quantity of enantiomers
non-superimposable mirror images of chiral molecules; same physical and chemical properties; opposite configuration at every chiral carbon
not mirror image stereoisomers, same configuration at one or more chiral carbons
has internal plane of symmetry
cis/ trans (Z/E)
different physical properties
describe position around double bond
Does cis or trans have higher boiling point?
cis has higher BP because of its permanent dipole moment
rotation about a single bond (ie. boat/ chair and eclipse/gauche)
cyclic forms of carbohydrates that differ in configuration about Carbon 1
breakdown of body fat by breaking carbon chain of lipid into 2-carbon pieces to enter the TCA cycle
aromatic protons range on NMR
neucleophilic acyl substitution, Oxygen of alcohol attacks and adds to carbonyl carbon of carboxylic acid (R-C=O-OH) and water is lost to form ester
What type of reaction are double bonds susceptible to?
hydrogen adds to the least substituted carbon
occurs when alkene reacts with hydrogen halides in UV light or peroxide
introduce acetyl group (R-C=O-CH3)
acetic anhydride (CH3-C=O-O-O=C-CH3)
reacts with alcohol and carbonyl groups, but not ethers
cation with positive charge on the carbon adjacent to the carbon of the double bond (CH2=CH-C+)
aprotic and polar
promotes SN2 and E2
CH3-C(=O)-CH3 [keto form]
CH3-C(-OH)=CH2 [enol form]