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Organic Chemistry - Final Exam With Complete Solutions Latest Update
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Organic Chemistry - Final Exam With CompleteSolutions Latest Update
Name the 6 polar aprotic solvents - correct answers acetone, acetonitrile, DMSO, DMF, HMPA, THF
Name the 5 polar protic solvents - correct answers acetic acid, ethanol, formic acid, methanol, water
______ and ______ mechanisms are two step reactions that have _____ intermediates. - correct answers SN1;
E1; 2 Intermediates each
______ and ______ mechanisms are one step reactions that have _____ intermediates. - correct answers SN2;
E2; 1 Intermediate each
Allylic - correct answers resonance stabilized (carbon bonded directly to a C=C)
______ always proceeds with a backside attack, causing an inversion of configuration at the stereogenic
center. The _______ and _______ group are 180° from each other. - correct answers SN2; Nucleophile; leaving
group
During an SN2 reaction, what happens during the backside attack of a ring? - correct answers Converts starting
material with a cis group to being trans
What is the process to determining which product of a (beta) elimination reaction is the major/minor? -
correct answers First apply the Zaitsev rule (the major product has the more substituted double bond); If a
mixture of stereoisomers is possible, the major product is the more stable stereoisomer.
Reaction Check List - correct answers SN1: ∧Nucl, ∨Base - 3°>, Protic (not 1°)
SN2: ∧Nucl, ∨Base - 1°>, Aprotic, (not 3°)
E1: Bulky/Nonnucl. Base - 3°>, ∨Base, Protic, (not 1°)
, E2: Bulky/Nonnucl. Base - 3°>, ∧Base, Aprotic, (not 1°)
When determining the more stable stereoisomer (to find the major product), what are 4 possible areas to look
at? - correct answers 1) If E2: Have to be anti-periplanar
2) If E1: Determine the more stable carbocation by higher R substitution
3) Alkene more stable when more R groups
4) Trans > Cis
Alkyne Synthesis is done with what type of reaction mechanism? How? - correct answers E2; two successive
dehydrohalogenation (E2) reactions
What ways can you gather enough information to rank substances by basicity? - correct answers 1) strongest
acid → weakest (conj.) base 2) As pKa of H-A gets smaller, the basicity of -A: increases 3) As Ka of H-A gets
larger, the weaker the -A:
Definition of Lewis Acid - correct answers electron pair acceptor; any e- deficient species that is capable of
accepting an e- pair is a Lewis Acid; any molecule or ionic species that can form new covalent bond by
accepting an e- pair; all BL acids are Lewis acids, but reverse is not necessarily true
Definition of Lewis Base - correct answers electron pair donor; structurally same as BL base (both have e- pair);
unlike BL base, Lewis can donate pair to anything electron deficient; any molecule or ionic species that can
form a new covalent bond by donating an e- pair.
Definition of B-L Acid. What requirements must they have? Give its symbol. - correct answers a proton donor;
must contain hydrogen; H-A
Definition of B-L Base. What requirements must they have? Give its symbol. - correct answers A proton
acceptor; must contain available e- pair (LP or π); B:
Any reaction in qhich one species donates an electron pair to another species is a _____________. - correct
answers Lewis Acid-Base Reaction
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