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Unformatted text preview: Seat # ‘ Name: Signature: / Lecture Section: ORGANIC CHEMISTRY
CHEMISTRY 307 Exam I October4, 2009 The exam has 5 multiple choice Questions and 7 written problems. Please answer
the multiple choice questions on the Opscan form. ' ON THE OpScan FORM:
(Use a Number 2 Pencil) (l) SIGN your name across the TOP of
the form. (2) code only the following
information: [blacken circles] (a), Your Name . . .‘LAST NAME
FIRST [blank space between last
andﬁrsz‘ name] (b) Your RU ID NUMBER [Start under Box A and continue
through to BOX 1] (c) Your LECTURE SECTION
NUMBER (Boxes K & L) (d) Your EXAM FORM NUMBER
(B ox P) Your EXAM FORM is: 1 1A. (9 pomts) A. Draw the structure of the isomer of Cngg that has a) the greatest number of primary hydrogens ' t
\N b) the greatest number of secondary hydrogens c) the greatest number of tertiary hydrogens 307 EXAM I DRAFT
FALL 2008 3 (9 points) B. Draw the structure that corresponds to each of the following incorrect
names and give it the correct IUPAC name ﬂ C’f/i/Cr 51‘!“ fl " /' it P '1
MW” 307 EXAM I DRAFT
FALL 2008 a) 4~1nethyl—4—neopentylheptane b) 2bromo4ethylpentane
'2 M f. “’7’ Q, 2, (#79: ﬂwﬂﬁ ,6 €;—~ (my? (' “~50 MW?” 2 ’Pﬂmem a. K!“ ﬂLtagmywﬁﬁﬂ E’Liyﬂéﬁbuéﬂgn c) isopentylcyclobutane My” \ gt“),
5’
5 Mvtvumnic L" * :2
V (ifﬁc fire—*ng lY. (9 points) A. Draw the structure of the isomer of CyHm that has a) the greatest number of tertiary hydrogens C /
0,24 /‘/ /kY/\rL/I\/\ b) the greatest number of primary hydrogens c) the greatest number of secondary hydrogens 0+3 ( (3g) 511+; 307 EXAM I DRAFT '
FALL 2008 5 IX (9 points) B. Draw the structure that corres
names and give it the correct IUPAC name a) 3chloro4—ethylpentane b) 4—11eopentylheptane we
M/x c) isobutylcyclopropane «a ..
r ,4' \~ (add earlr37“! (3” 307 EXAM I DRAFT
FALL 2008 6 ponds to each of the following incorrect n», 3
u .5 , r t::.,.~’11,f ""‘/ I
)
t. AA. UU pomts) A. Draw the two most impo rtant contributing structures for the molecule
with the formula C3H5N, which has a C =N bond, one bond and no rings. Be sure to ., Ma; ma» 44
“‘— ' A
"7 J 71””) T.
L, ’ 37
’ FIJ‘I‘M, "r 7 _ I . w, 4 1,5,1
B. How many hybrid orbitals are in this molecule? I Z ? 5,
C. What is the ideal CNH bond angle? I L0 41.. ’ D. Predict whether tl 1e actual bond angle will be ideal, greater than ideal, or less
than ideal. has 4—! B. What is the shortest bond in the molecule A.) H F. Which two atoms are connected by the strongest bond in the molecule? c. A) I
I (51 (1;) +’ 307 EXAM 1 DRAFT
FALL 2008 7 2Y. (10 points) A. Draw the two most important contributing structures for the molecule
with the formula C3H4O, which has a C=O and no rings. Be sure to show all valence shell lone pairs and all charges. No credit will be given for Parts B through F without
structures for Part A. (Hint: one of the structures has charges) '3
a 4—5 Crag, z Cal4" =1 4}
lg.
3?
J W i
“ii ($11 :‘x,’ (#l +7, ma mm; 1;, a” m ff 11
’4} ’01 4.991441) (’L' Q27». 9574» M ﬂj I / r’ f7 Mam] new!
f' 1
a Z?
4.. ,
m. 1.6 yr»! a trim
a} «as
l B. How many hybrid orbitals are in this molecule? C. What is the ideal CCO bond angle? 1 “IL ( D. Predict whether the actual bond angle will be ideal, greater than ideal. or less than ideal. #34,», “‘4” / E. What is the shortest bond in the molecule 1': "/’ ./
F. Which two atoms are connected by the strongest bond in the molecule? vi) "F / 307 EXAM I DRAFT
FALL 2008 8 DA. (1 U points) A. Write the propagation steps for the reaction of B
nbutyl bromide (l—bromobutane), 052de 0/ Him. ‘3 Cymwcﬁz. —,¢ r2 with butane to form ‘2 . p . a? ALT/ma: (
+/ Step1 ,‘I/M kiwi “eil'gtw’fimzl “3% ‘1“ e ’5"
ﬁ 1 “3:05;,‘Lél' 75 no» r
a rial€fwﬁ“"9b’
’7L/ Step2 (?W‘W>_ (C‘Df) w D. In ten words or less
the formation of one
thermodynamically t (only the ﬁrst ten words will be read) explain why
of these products is more favorable han the other. Be very speciﬁc in your answer.
+ l m Wmelw’j c,»# l3» MM.» a. 5‘31, (Etamg. 307 EXAM l DRAFT
FALL 2008 9 J1. clearly t H) pomts) A. Write the propagation steps for the reaction
(1 chlorobutane), nbutyl chloride B. Using the following bond energy data, calculate the AH" ° propagation step and of the overall reaction. (You must sh
for credit) @@%ﬂ$%ﬂeﬂg of each
ow your work 307 EXAM l DRAFT
FALL 2008 C. Using the bond energy data given
chlorination of butane to form 2—c ~ above. calculate AH" for the
hlorobutane. ‘ W!
\ / .1 ’q I’
"'/ 4,] “"[l‘jZ/ —/{/3/* :_ .../’;g/7I.;/€imf~’4_
\ I } D. In ten words or less
the formation of one thermodynamically than the other. 7% chtﬁucfj 13mm ma (only the ﬁrst ten words will be read) explain why
of these products is more favorable Be very speciﬁc in your answer. t” J" aﬁamtw f...«"b%z=b"t Cc c... t i; l.
l 4X. (9 points) A. Draw all the isomers of C5H 120 that do not have an 0—H bond. Use as
many boxes as you need 307 EXAM I DRAFT
FALL 2008 1 1 CH3 (347‘s;
/ J 4,. £1 ,,
.J rm
oa— ., .11” ‘ l c . Vi.
M] C; 1"}?! :3 (9 points) B. The compound 2ﬂuoro3methylpentane shown as a sawhorse projection CHZCH3 CH3 has three different staggered conformations resulting from rotation around the C23
bond. Use the three templates provided to draw the Newman projections of all three. (Place
C2 in front). Label the most stable conformation as X, the second most stable as Y, and
the least stable staggered conformation as Z. 307 EXAM I DRAFT
FALL 2008 12 'r 1 . K7 pUIHIS) A. uraw all the isomers of C5H13 N that have only one NH bond. Use as
many boxes as you need. 307 EXAM I DRAFT
FALL 2008 13 (9 points) B. The compound 2ﬂuoro3methylpentane shown as a sawhorse projection CH2CH3 has three different staggered conformations resulting from rotation around the C23
bond. Use the three templates provided to draw the Newman projections of all three. (Place
C2 in front). Label the most stable conformation as X, the second most stable as Y, and
the least stable staggered conformation as Z. 4/2. 9
x8 3‘0 6'74 W? l
a re r ’ . ,
at M will"; "i: '3 307 EXAM I DRAFT
FALL 2008 14 5X. (6 points) Draw a potential energy diagram, clearly labeling the axes, for the two step
reaction CH3C1 —+ CH3+ + Cl~ ; CH3+ + Br‘ ——+ CH3Br. (Bond Energies CCl 354
kJ/mol; C—Br 295 kJ/rnol). Do not include any numbers in your diagram. I ¢ F; Lap 1 *L ZZLWW) 307 EXAM I DRAFT
FALL 2008 15 J 1. u) p01an ) uraw a potenuat energy diagram, clearly labeling the axes, , for the two step
reaction CH3Br —+ CH3+ + Br" ; CH3+ + C1“ —> CH3C1. (Bond Energies C—Cl 354
kJ/mol; CBr 295 kJ/mol.) Do not include any numbers in your diagram. a ' cé:«w‘g,a, Jam“. X
L 307 EXAM I DRAFT
FALL 2008 I 16 6X (12 points) A. Using dotted line wedge projections and a ﬂat hexagon (and ignoring
optical isomerism), draw all nine possible monochlorination products that can form from
free radical chlorination of ethylcyclohexane. Assign each one a different roman
numeral. ‘ (ILn
,9 “ . M
Li 5 ’3'
gab!" \ gym/2’ ‘
1.0",
rah"V
7 AIL)
a“,
3 x
a " W
j!"H gravy
m ’3 in r "
__L )_ (bl R f B l.The two most stable products are roman numerals I, and
“V 7/ 4, t 2. The least stable product is roman numeral 1 V 3. Under uncontrolled conditions in which the relative reactivities of 1°,
2°, and 3° hydrogens are the same, the major product would be roman .+ ‘ numeral 1: 307 EXAM 1 DRAFT FALL 2008 17 6Y. ( 12 points) A. Using dotted line wedge projections and a ﬂat hexagon (and ignoring
optical isomerism), draw all nine possible monobromination products that can form
from free radical bromination of ethylcyclohexane. Assign each one a different Roman numeral. . B 1.The two most stablﬂejuﬁoducts in Mich the ring has two substituents are Roman numerals and 2. The least stable product is Roman numeral 3. Under uncontrolled conditions in which the relative reactivities of 1°,
2°, and 3° hydrogens is the same, the major product would be Roman numeral 307 EXAM I DRAFT
FALL 2908 1 8 /A. t 1U pomts) Use the templates to draw the indicated structures. 
A. The most stable and least stable conformation of l,3dimethylcyclohexane W + I most ﬂax/u B. The most stable and least stable conformation of cisl—chloro4—
methylcyclohexane ' / Qh‘s E. Given that a gauche butane interaction is 4 kJ/mol calculate the difference in strain energy between the most stable conformation of cis—l,2—dimethyl cyclohexane and the
least stable chair conformation of transl,4—dimethylcyclohexane ' 2. a” “a? W “(LEW/g 4er T1 l‘lg’i 4 1x“ "534% 1L {M Energy difference ’ 6" L 2' VI #1:)» n,ij
{W k 307 EXAM I DRAFT
FALL 2008 19 7Y. ( 10 points) Use the templates to draw the indicated structures.
A The most stable and least stable conformation of trans1bromo3 ethylcyclohexane i ~ “Ii/0&3 D. The most stab e and least stable conformaionzof cis—liodo—4—ﬂuorocyclohexane l 4
H ~ ’C
I I last
I Jiliost E. Given that a gauche butane interaction is 4 kJ/mol calculate the difference in strain
energy between the most stable conformation of cis1,4dimethyl cyclohexane and the
least stable chair conformation of trans—l ,2dimethylcyclohexane ~€a= 1%‘4: fir/M Q0”: leL/tlc’éfzi‘ufe
*‘l’ 7/4”
[Algal/53v L Energy difference Elf 307 EXAM I DRAFT
FALL 2008 20 1 Which of the following is/are isoelectronic with H30+? NH3 CH3' CH3“
a ’ b _ c A. b and d B. c and d C. a and d aandc
. b 2.. Which of the following species have a dipole moment greater than zero?
H C $1 ‘
3 H_(‘:_H % H3C—O—~CH3
H3C cx . .
' a b c d c and (1
only d
a, b, and d A
B.
C. @ b and d
E. all of them 3. Which of the following species are nucleophiles?
BF4’ (3143+ H20 1'
a b c I d
A. a and d
b and c
C. c and d
D. a, c, and d
E. all of them
' 307 EXAM I DRAFT FALL 2008 l 4. ‘ Which of the following species have an HCH bond angle greater than 109.50 and less
than 120° ? CHgBr ‘ CH2=CHCH3 :CHg' CH3+ a b c d a and b
c and d
a and c
a, b, and c
all of them yuccaIQ 5. What color is your exam?
A. White
B. Pink
C. Blue
D. Yellow
307 EXAM I DRAFT FALL 2008 2 ...
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This note was uploaded on 09/30/2010 for the course CHEM 307 taught by Professor Several during the Fall '08 term at Rutgers.
 Fall '08
 Several
 Organic chemistry

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