_O__RGANIC CHEMISTRY(II); Mid-term Exam.

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Problem 1 (10 Points) Chap. 13: Structural Determination: NMR

a) Why are we studying 1H- NMR & 13C-NMR? (2 Points)
b) Explain the principle of NMR spectroscopy. (4 Points)
c) Explain the "chemical shifts" in NMR spectra. (2 Points)
d) Calculate the amount of energy (in KJ/mol) corresponding to (6; 6) in 200 MHz
NMR: h=6.62xl0-'6! erg.sec, 1 erg = lxl0-7 J, C = 3 x 1010 cm/sec. (4 Points)

Problem 2 (10 Points); Chapter 13: 13C-NMR

Predict the number of carbon resonance lines you would expect in the 13C- NMR
spectra of the following compounds; Draw the chemical structure.
a) tert- Butylcyclohexane, b) cis-1,2-Dimethylcyclohexane, c) Cyclohexanone
d) 2- Methyl- 3- pentanone, e) 2,3-Dimethyl- 2- pentene

Problem 3 (8 Points) Chap. 13: 1H- NMR

Draw structures for comp0unds that meet the following descriptions:
a) 따Q; one singlet, b) C펴£1; one doublet and one sep區
c) C뿌h(); two triplets, d) C4Ha02; one singlet, one triplet처nd one quartet

j;roblem 4 (10 Points); Chapter 14

Give the structures of the likely products from reaction of 1 equivalent of HCl with
2-methylcyclohexa-1,3-diene. Show the chemical structures of the C intennediates.
Give the products name according to the IUPAC system

ioblem 5 (10 Points); Chapter 14

Calculate the energy (in KJ/mol) range of electromagnetic radi~tion in the UV region
of the spectrum from 200 to 400 run. How does this value compare with the values
for IR (400 to 4000 wave number) and NMR (200 MHz) spectroscopy? Evaluate the
required energies.

Problem 6 (10 Points) ; Chapter 15

(a} Show the relative energy levels of the seven x molecular orbitals (MOs) of the
cycloheptatrienyl system. At first, show the chemical structures, and next, fill the 1t
electrons. Tell which of the seven orbitals are filled in the cation, radical, and anion,
and account for the aromaticity of the cycloheptatrienyl cation. (8 Points)
(b) What does it mean the (4n + 2) rule for aromaticity? (2 Points)
Probl em 7 (10 Points ) Chap. 16
a) Show the energy diagram of the formation of carbocations for the
electrophilic
bromination of alkene and benzene. (5 Points )
b) What is the major monosubstitution product from the Friedel-Craf
t reaction of
benzene with 1- chloro- 2- methylpropane in the presence of AlCb . (5
Points )

Probl em 8 (10 Points ) Chap. 16

Draw resonance structures for the intermediates from reaction of
an electrophile at
the ortho and meta positions of nitrobenzene. Which position is favored
? Why?

Proble m 9 (20 Points ) Chap. i7

How can you prepare 1,4- pentanediol from 3- bromopropan- 1- ol and

acetaldehyde?
Show the detail reaction processes.

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