ORGANIC CHEMISTRY ACS FINAL EXAM QUESTION AND ANSWERS

  ketone - Correct Answers: aldehyde - Correct Answers: carboxylic acid - Correct Answers: ester - Correct Answers: amide - Correct Answers: anhydride - Correct Answers: amine - Correct Answers: ether - Correct Answers: constitutional isomers - Correct Answers: same formula, different connectivity stereoisomers - Correct Answers: same formula, different spatial arrangement enantiomers - Correct Answers: non-superimposable mirror images diastereomers - Correct Answers: stereoisomers that are not mirror images of each other R configuration - Correct Answers: clockwise S configuration - Correct Answers: counter clockwise what functional groups does a peptide bond contain - Correct Answers: amide what functional groups does a lipid contain - Correct Answers: esters what functional groups do amino acids contain? - Correct Answers: aromatic rings meso compound - Correct Answers: molecule with multiple stereo centers and it is superimposable on its mirror image NO2 prefix - Correct Answers: nitro CH=CH2 prefix - Correct Answers: vinyl CH2CH=CH2 prefix - Correct Answers: allyl phenol - Correct Answers: benzoic acid - Correct Answers: aniline - Correct Answers: toluene - Correct Answers: three types of disubstituted benzenes - Correct Answers: ortho-1,2 meta-1,3 para-1,4 only use when you have ONLY 2 substituents benzene - Correct Answers: as you increase heat of combustion, what happens stability? - Correct Answers: it decreases Carbon 13 NMR Resonances - Correct Answers: 0-80 sp3c 125-150 aromatic 160-180 esters/acids 200-220 aldehydes/ketones H 1 NMR Resonances - Correct Answers: 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 - Correct Answers: 3400 OH and NH 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? - Correct Answers: benzyl has CH2 in between the ring and the substituted chain bond angle for sp2 hybridized? - Correct Answers: 109.5 what are 2 key things to lewis structures? - Correct Answers: 1. filled octets 2. electronegative atom has negative charge if a ring has a charge, then it is ____ - Correct Answers: aromatic a strong acid corresponds to? - Correct Answers: a weak base what does a double bond right next to acidic H mean? - Correct Answers: it is more acidic low pKa value means it is... - Correct Answers: more acidic how does hybridization relate to acidity? - Correct Answers: the more S character it is, the more acidic spsp2sp3 a hydrogen next to an electronegative atom will always be... - Correct Answers: more acidic how do you determine if molecules are meso isomers? - Correct Answers: needs to be chiral and needs to have a plane of symmetry how do you find most stable newman projection? - Correct Answers: it will have less gauche interactions what are wedges and dashes in fischer projections? - Correct Answers: horizontal-wedge vertical-dash if only one stereo center is flipped in a molecule, they are... - Correct Answers: diastereomers do racemic mixtures get plane polarized light? - Correct Answers: no, they cancel each other out do meso compounds get plane polarized light? - Correct Answers: no, they cannot bend light what can triple bonds not do stereoisomerically? - Correct Answers: exhibit cis or trans what can an enantiomer not have? - Correct Answers: a plane of symmetry what happens with a dehydrohalogenation reaction? - Correct Answers: H wants to attack and form a double bond to increase stability a strong acid corresponds to a ________ nucleophile - Correct Answers: weak how do you tell if it is a syn or anti addition? - Correct Answers: Syn- two atoms are either both forward/back Anti-one atom forward and one back where does hydroboration put the substituent? - Correct Answers: on the less substituted side (anti-markovnikov) what are the most stable types of free radicals? - Correct Answers: allylic or benzylic tertiarysecondaryprimary what are the 3 steps of a free radical reaction? - Correct Answers: 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? - Correct Answers: very low activation energy what does non-regioselective mean in terms of energy? - Correct Answers: it goes down in energy what does it mean if an alcohol absorbance peak on the IR spectrum is abnormally wide? - Correct Answers: it is a carboxylic acid what does chromic acid do? - Correct Answers: 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 - Correct Answers: tertiary what is the trick for predicting major products of E2 reactions? - Correct Answers: 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? - Correct Answers: hydroboration-oxidation how could you tell if a pair were resonance structures? - Correct Answers: atoms cannot be moved, only pi bonds and lone pairs which is more acidic: OH or NH? - Correct Answers: OH which hybridization is the most acidic? - Correct Answers: spsp2sp3