Chemistry Department
CHEM 263 B1
Exam I
Thursday, February 10, 2011
- The IR and 1H
NMR spectra of a compound of molecular formula C11H16O
are given below.
SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/
(National Institute of Advanced Industrial Science and Technology, 6 January
2011)
a. Calculate
the degree of unsaturation. (1 point)
b. List
the possible functional groups gleaned from the molecular formula. (2 points)
c. What
is the functional group that the IR spectrum shows to be present in the
unknown? (2 point)
d. Propose
a structure for this compound. (10 points)
- Propose a
structure for the compound that fits the following data: (5 points)
C4H7BrO2 d = 1.08 ppm (3H,
triplet)
d = 2.07 ppm (2H,
quintet)
d = 4.23 ppm
(1H, triplet)
d = 10.97 ppm
(1H, singlet)
- Sketch the
expected 1H NMR spectrum of the following compound: (10 points)
- When a
solution of 1,3-butadiene in CH3OH is treated with chlorine,
the products are the following:
a.
Propose a mechanism to account for
their formation. (10 points)
b.
Which is the product of thermodynamic
control? (2 points)
- Give the
structure(s) of the principle organic products of the following reactions:
(6 points)
a.
b.
- Explain why
borazole is a very stable compound. (3 points)
- Name the
following compound: (2 points)
- Draw the
structure of m-tert-butylaniline.
(2 points)
- When
benzene is mixed with an excess of D2SO4 (deuterated
sulfuric acid) at room temperature, the atoms of hydrogen in the benzene
molecules are slowly replaced by deuterium. Propose a mechanism which explains this
observation. (6 points)
- Provide a synthetic pathway for the
following transformation: (6 points)
- Identify the diene and the dienophile that you would
use to synthesize the following compound: (4 points)
