Chem 210 PSU exam 2
Latest edition 2024
Taking into account ring strain, which of the following is the most stable?
Correct answer: A
How many different meso compounds exist for dibromocyclohexane (C6H10Br2)?
(a) 1
(b) 2
(c) 3
(d) 4
(e) 5
Correct answer: B
Conformer 2 is more stable than conformer 1 by 0.30 kcal/mol. What is the 1,3-diaxial
strain (per axial hydrogen in kcal/mol) for SPh?
(a) 0.65
(b) 0.80
(c) 0.95
(d) 1.25
(e) 1.90
Correct answer: B
Estimate the strain energy (in kcal/mol) of trans-1,2-dimethylcyclopropane (1). [Hint:
Comparing to the unsubstituted cyclopropane, what are the additional strain
contributions?]
(a) 25.2
(b) 27.6
(c) 28.5
(d) 29.2
(e) 30.6
Correct answer: D
A
What is true about the entropy of the reaction below? (a) ΔS > 0
(b) ΔS = 0
(c) ΔS < 0
(d) it cannot be determined
Correct answer: A
How many bonds are made and broken in the one-step reaction shown below?
bonds broken bonds made
(a) 3 3
(b) 3 2
(c) 2 3
(d) 2 1
(e) 2 2
Correct answer: E
In the radical-chain chlorination reaction all hydrogens can be replaced by chlorines,
one by one. Considering only mono-substitution, how many constitutional isomers
formed in the reaction below are chiral?
(a) 0
(b) 1
(c) 2
(d) 3
(e) 4
Correct answer: C
Many natural products contain cyclohexane ring "locked" in the boat conformations by a
one-carbon bridge. How many C-H//C-H bond eclipsing interactions are there in
camphor, one of such natural products?
(a) 1
(b) 2
(c) 3
(d) 4
(e) 5
Correct answer: B
Which of the following structures represents the lowest energy form of (1S, 3S)-1,3-
dichlorocyclohexane?
Correct answer: C
Compare the two dimethyl derivatives shown below. For each cycloalkane, which
isomer is more stable, cis or trans?
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(a) cis cis
(b) cis trans
(c) trans cis
(d) trans trans
Correct answer: C
What is the correct order of priorities for the groups listed, starting with the highest
priority group? [Hint: Draw full Lewis structures for the groups.]
(a) -CN > -CHNCH3 > -CH2OH
(b) -CN > -CH2OH > -CHNCH3
(c) -CHNCH3 > -CH2OH > -CN
(d) -CHNCH3 > -CN > -CH2OH
(e) -CH2OH > -CN > -CHNCH3
(f) -CH2OH > -CHNCH3 > -CN
Correct answer: E
Are the ring fusions I and II in estrone (a female hormone) cis or trans?
I II
(a) cis cis
(b) cis trans
(c) trans cis
(d) trans trans
Correct answer: D
One chair conformation of 1,1,3-trimethylcyclohexane is more stable than the other by
3.6 kcal/mol. What is the strain energy of the 1,3-CH3//CH3 diaxial interaction?
(a) 6.3
(b) 5.4
(c) 4.5
(d) 3.6
(e) 2.7
Correct answer: D
What is absolute configuration of the stereogenic carbons in compound below?
(a) 2S, 4S
(b) 2R, 4R
(c) 2R, 4S
(d) 2S, 4R
Correct answer: A
How many stereogenic centers are there in in the structure below?
(a) 1
(b) 2
(c) 3
(d) 4
(e) 5
Correct answer: E
The enzyme-catalyzed addition of water, HO- and H- respectively, to the carbons of the
double bond results in the indicated stereochemistry of the product as shown below. On
what face of the reactant does the addition of -OH take place, and what is the pro-
chirality of the encircled hydrogen?
-OH -H
(a) Re pro-R
(b) Re pro-S
(c) Si pro-R
(d) Si pro-S
Correct answer: D
Based on the structure of 1, which statement must be true?
(a) 1 is levorotatory
(b) 1 is meso
(c) 1 has [α]D = +112
(d) 1 is R
(e) 1 has an achiral diastereomer.
Correct answer: E
Which of the following cannot exist among stereoisomers of 1,2-dimethylcyclohexane?
(a) cis R,R axial, equatorial
(b) cis R,S axial, equatorial
(c) trans R,R axial, axial
(d) trans S,S equatorial, equatorial
Correct answer: A
What is the relationship between the two compounds shown below?
(a) identical
(b) constitutional isomers
(c) enantiomers
(d) diastereomers
Correct answer: D
Which reaction profile represents an endergonic two-step reaction wherein the first step
is rate-limiting?
Correct answer: E
What are the electrophiles and nucleophiles in the two-step reaction shown below?
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(a) N E N E
(b) N E E N
(c) E N N E
(d) E N E N
Correct answer: B
Based on the enthalpies of formation given below, what is the C-Cl bond dissociation
energy in CH3-Cl (in kcal/mol)?
ΔHf(Cl•) = 29 kcal/mol
ΔHf(H3C•) = 35 kcal/mol
ΔHf(H3CCl) = -20 kcal/mol.
(a) 84
(b) 55
(c) 44
(d) 26
Correct answer: A
Which of the following reaction is an addition?
(a) CH3Br + KOH → CH3OH + KBr
(b) CH3CH2Br → H2C=CH2 + HBr
(c) H2C=CH2 + H2 → CH3CH3
(d) H2C=CH-CH2CH3 → H3CCH=CHCH3
Correct answer: C
Consider two chair conformations of cis-1-chloro-2-methylcyclohexane. What is the
approximate %-fraction of the less stable conformer at equilibrium at 25 ºC?
(a) 2%
(b) 5%
(c) 10%
(d) 20%
(e) 27%
Correct answer: C
How many stereoisomers are possible for the following molecule?
(a) 8
(b) 4
(c) 3
(d) 2
(e) 1
Correct answer: B
