Organic Chemistry ACS Final Exam

ketone

aldehyde

carboxylic acid

ester

amide

anhydride

amine

ether

constitutional isomers

same formula, different connectivity

stereoisomers

same formula, different spatial arrangement

enantiomers

non-superimposable mirror images

diastereomers

stereoisomers that are not mirror images of each other

R configuration

clockwise

S configuration

counter clockwise

what functional groups does a peptide bond contain

amide

what functional groups does a lipid contain

esters

what functional groups do amino acids contain?

aromatic rings

meso compound

molecule with multiple stereo centers and it is superimposable on its mirror image

NO2 prefix

nitro

CH=CH2 prefix

vinyl

CH2CH=CH2 prefix

allyl

phenol

benzoic acid

aniline

toluene

three types of disubstituted benzenes

ortho-1,2

meta-1,3

para-1,4

only use when you have ONLY 2 substituents

benzene

as you increase heat of combustion, what happens stability?

it decreases

Carbon 13 NMR Resonances

0-80 sp3c

125-150 aromatic

160-180 esters/acids

200-220 aldehydes/ketones

H 1 NMR Resonances

0.9-1.5 sp3 C

2-2.5 allylic H

3-4.5 O-CH3

4.5-6.5 vinylic

7-8.5 aromatic

10 aldehyde

10-12 carboxylic acid

IR Resonances

3400 OH and NH

3100-3000 sp2 C

2100 triple bonds

1700 ketones

1600 C=C, aromatic C-C

1500 aromatic C-C

what is the difference between phenyl and benzyl?

benzyl has CH2 in between the ring and the substituted chain

bond angle for sp2 hybridized?

109.5

what are 2 key things to lewis structures?

1. filled octets

2. electronegative atom has negative charge

if a ring has a charge, then it is ____

aromatic

a strong acid corresponds to?

a weak base

what does a double bond right next to acidic H mean?

it is more acidic

low pKa value means it is...

more acidic

how does hybridization relate to acidity?

the more S character it is, the more acidic

sp>sp2>sp3

a hydrogen next to an electronegative atom will always be...

more acidic

how do you determine if molecules are meso isomers?

needs to be chiral and needs to have a plane of symmetry

how do you find most stable newman projection?

it will have less gauche interactions

what are wedges and dashes in fischer projections?

horizontal-wedge

vertical-dash

if only one stereo center is flipped in a molecule, they are...

diastereomers

do racemic mixtures get plane polarized light?

no, they cancel each other out

do meso compounds get plane polarized light?

no, they cannot bend light

what can triple bonds not do stereoisomerically?

exhibit cis or trans

what can an enantiomer not have?

a plane of symmetry

what happens with a dehydrohalogenation reaction?

H wants to attack and form a double bond to increase stability

a strong acid corresponds to a ________ nucleophile

weak

how do you tell if it is a syn or anti addition?

Syn- two atoms are either both forward/back

Anti-one atom forward and one back

where does hydroboration put the substituent?

on the less substituted side (anti-markovnikov)

what are the most stable types of free radicals?

allylic or benzylic

tertiary>secondary>primary

what are the 3 steps of a free radical reaction?

initiation-goes from 0-1 radicals

propagation- goes from 1 to another 1

termination-goes from 2-0 radicals

what is the energy of propagations like?

very low activation energy

what does non-regioselective mean in terms of energy?

it goes down in energy

what does it mean if an alcohol absorbance peak on the IR spectrum is abnormally wide?

it is a carboxylic acid

what does chromic acid do?

it turns C-H bonds into C-O bonds

if a molecule does not have C-H bonds, it will be unreactive with chromic acid

E2 reactions favor ______ alkyl halides

tertiary

what is the trick for predicting major products of E2 reactions?

if the base is sterically hindered, then the major product will be the LESS substituted alkene

if the base is NOT sterically hindered, then the major product is the more substituted alkene

what is the reagent BH3 * THF used for?

hydroboration-oxidation

how could you tell if a pair were resonance structures?

atoms cannot be moved, only pi bonds and lone pairs

which is more acidic: OH or NH?

OH

which hybridization is the most acidic?

sp>sp2>sp3