Exam 1

Fall 11: Exam 1
Ch 1-4
100 points
Name
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Answer all the questions.
1-10 are True / False. (20pts)
1)
Organic chemistry is the study of carbon containing compounds
2)
A triple bond has two π bonds and one σ bond
3)
A  bond must be polar
4)
Nitrogen is more electronegative than Phosphorous
5)
Cyclopropane has more ring strain than cyclobutane
6)
Beryllium has 4 valence electrons
7)
Barium’s valence electronic configuration is 6s2
8)
F— is more stable than Br— and therefore HF is more acidic than HBr
9)
The Hammond Postulate states that G = H — TS
10)
A  bond places electron density directly between the atoms being
bound together and is cylindrically symmetrical
11) Circle the acid in each of these reactions. (6pts)
(a) HCl
+
H2O  H3O+
+
Cl-
(b) CH3CH2OH
+
NaOH → CH3CH2ONa +
(c) CH3CH2O-
+
CH3-Br  CH3CH2OCH3 + BrFall11org1exam1.doc
H2O
page1
12) (20pts) For the following molecule, calculate the number of …
a) carbon atoms
b) hydrogen atoms
c) π bonds
d) fluorine atoms + oxygen atoms
e) sp2 hybridized carbons
f) sp hybridized atoms
g) sp3 hybridized carbons
h) lone pairs (non bonding pairs) of electrons
i) the C-O-C bond angle
j) carbons in the ring
Fall11org1exam1.doc
page2
13) Draw two molecules that are isomers. (4pts)
14) Name the following compounds in IUPAC form: (8pts)
15) Draw the following compounds
(8pts)
3-ethyl-2-methylhexane
1,1-dipropylcyclopropane
Fall11org1exam1.doc
page3
16) Using these four energy level diagrams (A-D), pick the most
appropriate. (10pts)
a) which is the most exothermic ?
b) which has the most steps ?
c) which has the rate determining step as the 2nd step ?
d) which would have the largest equilibrium constant ?
e) which would be the most regioselective for a radical abstraction ?
Fall11org1exam1.doc
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17) What is meant by the scientific term radical species (2pts)?
18) Using “fish hook” arrows (which represent movement of ONE electron),
draw the mechanism for the two propagation steps that the result in the
formation of chloromethane. (6pts)
Cl
H3C
H—CH3

Cl—Cl
H—Cl

CH3—Cl
Fall11org1exam1.doc
CH3
Cl
page5
19) Circle the most stable member of each threesome.
Fall11org1exam1.doc
(16pts)
page6
Bonus Question for up to 3 points.
Explain why the correct IUPAC name for CH3CH(CH3)CH3 is
methylpropane, and not 2-methylpropane.
Fall11org1exam1.doc
page7

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