1. Predict the structure(s) of the expected major organic product(s). Unless mentioned otherwise,
assume that all reagents are present in excess. Show stereochemistry where needed and write
NR if there is no reaction. Write the type of reaction such as SN1, SN2, E1, E2, oxidation,
reduction, acid-base etc in the given box. (40 pts)
1) LiAIH4, THF
1) CH3CH2MgBr, ether
2. Mechanism: Write complete, detailed, stepwise arrow pushing mechanism for the following
and draw the stucture of all intermediates. (9 Pts)
reaction. Include all steps, show the direction of arrows, write all non-zero charges,
3. Nomenclature: Give the IUPAC name the following molecule, include absolute stereochemistry
if present. (12 pts)
5. Using the following IR and NMR spectra, draw a possible structure for C6H12O in the given box. (10 pts)
Degree of unsaturation -
IR: 2850cm-¹ and 2750cm medium sharp, 1750 cm-¹ strong sharp.
4. (20 pts) Vocabulary: Fill in the blanks with the appropriate word. If two or more words
are given, circle the correct one.
a) In SN1 reactions of haloalkanes, a leaving group leaves before / after / at the same time
as the nucleophile enters and is always / sometimes / never accompanied by an
b) As we go don the periodic table, leaving group ability of atoms increase / decrease.
c) Alcohols have higher / lower / same boiling point than haloalkanes of same size because
they can form
and they are more / less / same soluble in water than
d) Inductive effect increases as the size of the halogen atom increases / decreases and as
the distance between the acidic proton and the halogen increases / decreases. As
inductive effect increases, the acid becomes weaker / stronger / unaffected.
e) Alkyl and hydride shifts always / sometimes / never happen in SN2 reactions.
f) In E2 eliminations, strong bulky bases tend to form Hofmann / Saytzev product, which is
the more / less substituted alkene product.
g) Molecules that are superimposable mirror images are chiral / achiral.
between these kind of molecules is enantiomers / same meso / diastereomers.
h) In SN1 reactions, if we start with an optically active haloalkane, the stereocenter in the product
becomes racemic / inverted / retained.
atoms or the
i) In organic chemistry, oxidation is defined as the removal of
atoms to a molecule.
j) For an E2 reaction to happen the leaving group and a hydrogen atom must be
to one another.
k) In aqueous media, primary alcohols are oxidized to a(n)
while secondary alcohols are oxidized to a(n)
5. Identify Enantiomers the relationship (E), Diastereomers between (D), the Identical following Chiral molecules (I) and as Same Constiutional Meso (M). Isomers (9 pts) (C),
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