Organic Chem II - Exam 2
(2026-2027)
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, How can 2-methoxy-2-methyl-1-cyclohexanol be 1) H2, Pt
prepared from 3-methylcyclohexene? 2) Br2, hν
3) NaOEt
4) mCPBA
5) H2SO4, MeOH
Sulfides are easily _______ and ______. oxidized and make ideal reducing agents
which reagents will be needed for this reaction? c. i) Hg(OAc)₂, ROH / ii)NaBH₄
(image on pg 1)
a. i)NaH / ii) CH₃I
b. Hv, MeOH
c. i) Hg(OAc)₂, ROH / ii)NaBH₄
d. O₂
Thiols can occur with _________ with no competing Secondary Alkyl Halides, -SH, Poor
reactions because ____ is an excellent nucleophile and a
_____ base.
Which IUPAC name below represents the naming b. 2,3-epoxy-3-ethyl-2-methylpentane
method where Oxygen is used as a substituent.
a. 2-diethyl-3-dimethyloxirane
b. 2,3-epoxy-3-ethyl-2-methylpentane
c. 2,3-diethyl-3,3-dimethyloxirane
d. 2,2-epoxy-3,3-dimethyloxirane
Why does the S=O bond have very little double bond The 3p orbital of sulfur is larger than the 2p orbital of Oxygen and the orbital
character? overlap of the population bond is not effective. Because of this, the double
bond to Oxygen is often drawn as a single bond.
Explain Thermodynamics control vs. Kinetic control Thermodynamic control is done at elevated temps where competing pathways
are reversible and there is enough energy to lose a leaving group and reform
allylic+. Equilibrium is established and product distribution depends on the
relative energy of the pdt. (Lower E=major product). Where as Kinetic control is
done at low temps where the competing reaction pathways are irreversible and
1,2-addition occurs more rapidly. There is not enough energy to convert the 1,2-
adduct back into allylic+. The product distribution is determined by relative
rates. (Faster —> product)
A conjugated polyene undergoes ____________. cyclization