CHEM 115 Georgetown Exam1(2002)

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ORGANIC CHEMISTRY I (CHEM 115/CNED 013)
EXAM #1
September 23, 2002
Name:_____________________________________
1. _____/24 5. _____/12 9. _____/15
2. _____/15 6. _____/20 10.______/35
3. _____/15 7. _____/30
4. _____/10 8. _____/24 TOTAL: ______/(200)
Please read each question carefully before you begin. Your exam should have a total of 6 pages.
You will have two hours in which to complete this exam; be sure to save time to check your
answers after you’re finished. The backs of the pages may be used for rough work, but your
answers should be written clearly on the front of the page in the spaces provided. Molecular models
may be used. Show your work clearly, and you may receive partial credit for partially correct
answers. Good luck!
Table 1. Energy Costs for Interactions in Alkane Conformers (E in kcal/mol)
Gauche Eclipsed
H , H 0 1
H, CH3 0 1.4
H, CH2CH3 0 1.5
CH3, CH3 0.9 2.6
CH3, CH2CH3 1 3.6
CH2CH3, CH2CH3 1.2 4.0
Table 2. Energy Difference Between the Axial and Equatorial Conformations of Substituted
Cyclohexanes
Substituent Eax-Eeq (kcal/mol) Substituent Eax-Eeq (kcal/mol)
-F 0.2 -CH2OH 1.8
-CN 0.2 -CH3 1.7
-Cl 0.5 -CH2CH3 1.8
-Br 0.6 -CH(CH3)2 2.1
-OH 1.0 -C(CH3)3 5.4
Table 3. Bond Dissociation Energies for Homolytic Cleavages (kcal/mol)
H-H 104 C-Br 68 N-H 93 C=O 176
Br-Br 46 O-H 111 C-C 83 200
H-Br 87 C-H 98 C=C 146
H-Cl 103 Cl-Cl 58 C-Cl 84
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1. (4 pts each, 24 total) For each of the functional groups listed below, draw a complete neutral
molecule that contains the listed functional group. (just one functional group per molecule, please)
ketone
alcohol
amine
alkyne
ester
ether
2. (5 pts each, 15 total) Provide a name for each of the following molecules. You may use either
IUPAC names or common names, where appropriate.
(a)
CH3
H3CCH3
H
(b)
(c)
3. (5 pts each, 15 total) Draw a structure for each compound (low energy conformation please).
(a) (CH3)3CCH2CH(C(CH3)3)CH2CH3
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