Organic chemistry ii – exam 2
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A(n) ______ group contains sulfur bonded to hydrogen. - Answer-Thiol or mercapto
Low temperatures are used to achieve-
A) Thermodynamic control
B) Reactant control
C) Kinetic control
D) Product control
E) None of the above - Answer-C) Kinetic control
What is the purpose of dimercaprol, and how does it work? - Answer-Dimercaprol is used to
treat mercury and lead poisoning. Dimercaprol contains two thiol groups that can form metal
complexes to bind to mercury and other toxic metals and remove them from the body.
Why do equilibrium reactions favor the formation of reactants at high temperatures? - Answer-
Using the Gibbs free energy equation, ΔG = ΔH - TΔS, will determine whether the reaction will
favor reactants or products. In cases where only one of the terms is negative, temperature will
determine which term has a greater magnitude which will cause ΔG to be negative or positive.
In a synthesis reaction, entropy will be negative, the entropy term will be positive, and the
,temperature will determine whether that positive term is large enough to cause a positive ΔG
(favors reactants). Therefore, a high temperature is needed to favor reactants.
How can 2-methoxy-2-methyl-1-cyclohexanol be prepared from 3-methylcyclohexene? -
Answer-1) H2, Pt
2) Br2, hν
3) NaOEt
4) mCPBA
5) H2SO4, MeOH
Sulfides are easily _______ and ______. - Answer-oxidized and make ideal reducing agents
which reagents will be needed for this reaction?
(image on pg 1)
a. i)NaH / ii) CH₃I
b. Hv, MeOH
c. i) Hg(OAc)₂, ROH / ii)NaBH₄
d. O₂ - Answer-c. i) Hg(OAc)₂, ROH / ii)NaBH₄
Thiols can occur with _________ with no competing reactions because ____ is an excellent
nucleophile and a _____ base. - Answer-Secondary Alkyl Halides, -SH, Poor
Which IUPAC name below represents the naming 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 - Answer-b. 2,3-epoxy-3-ethyl-2-methylpentane
Why does the S=O bond have very little double bond character? - Answer-The 3p orbital of
sulfur is larger than the 2p orbital of Oxygen and the orbital 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 - Answer-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 ____________. - Answer-cyclization
The difference in energy between staggered and eclipsed conformations of ethane is known as
which of the following?
· Ring strain
· Torsional strain
· Steric strain
· None of the above - Answer-Torsional strain
What is conjugated pi systems relationship with light? - Answer-Conjugated pi systems have an
ability to interact with light. There are certain conditions that are right for the interaction to
happen between light and these systems. Those conditions are when a e- in the HOMO can
absorb a photon of light w/ E necessary to promote the e- to the LUMO. Reactions that are
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answers | cOmpLete study guide fOr
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A(n) ______ group contains sulfur bonded to hydrogen. - Answer-Thiol or mercapto
Low temperatures are used to achieve-
A) Thermodynamic control
B) Reactant control
C) Kinetic control
D) Product control
E) None of the above - Answer-C) Kinetic control
What is the purpose of dimercaprol, and how does it work? - Answer-Dimercaprol is used to
treat mercury and lead poisoning. Dimercaprol contains two thiol groups that can form metal
complexes to bind to mercury and other toxic metals and remove them from the body.
Why do equilibrium reactions favor the formation of reactants at high temperatures? - Answer-
Using the Gibbs free energy equation, ΔG = ΔH - TΔS, will determine whether the reaction will
favor reactants or products. In cases where only one of the terms is negative, temperature will
determine which term has a greater magnitude which will cause ΔG to be negative or positive.
In a synthesis reaction, entropy will be negative, the entropy term will be positive, and the
,temperature will determine whether that positive term is large enough to cause a positive ΔG
(favors reactants). Therefore, a high temperature is needed to favor reactants.
How can 2-methoxy-2-methyl-1-cyclohexanol be prepared from 3-methylcyclohexene? -
Answer-1) H2, Pt
2) Br2, hν
3) NaOEt
4) mCPBA
5) H2SO4, MeOH
Sulfides are easily _______ and ______. - Answer-oxidized and make ideal reducing agents
which reagents will be needed for this reaction?
(image on pg 1)
a. i)NaH / ii) CH₃I
b. Hv, MeOH
c. i) Hg(OAc)₂, ROH / ii)NaBH₄
d. O₂ - Answer-c. i) Hg(OAc)₂, ROH / ii)NaBH₄
Thiols can occur with _________ with no competing reactions because ____ is an excellent
nucleophile and a _____ base. - Answer-Secondary Alkyl Halides, -SH, Poor
Which IUPAC name below represents the naming 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 - Answer-b. 2,3-epoxy-3-ethyl-2-methylpentane
Why does the S=O bond have very little double bond character? - Answer-The 3p orbital of
sulfur is larger than the 2p orbital of Oxygen and the orbital 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 - Answer-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 ____________. - Answer-cyclization
The difference in energy between staggered and eclipsed conformations of ethane is known as
which of the following?
· Ring strain
· Torsional strain
· Steric strain
· None of the above - Answer-Torsional strain
What is conjugated pi systems relationship with light? - Answer-Conjugated pi systems have an
ability to interact with light. There are certain conditions that are right for the interaction to
happen between light and these systems. Those conditions are when a e- in the HOMO can
absorb a photon of light w/ E necessary to promote the e- to the LUMO. Reactions that are
