Exam 2: Chapter 5, 14, 15 _________________________________________

15 pts. each question.

1. Draw the molecule having formula C3H8O which has an IR absorption 2850-3000 cm-1, but
no absorption in the range 3200-3600 cm-1.

No -OH peak in IR, so:

2. Draw any molecule which contains at least one stereocenter but contains no center of
chirality.

On the very first page of CH5 notes posted on Canvas, we had the example of 2-butene
molecules which contain stereocenters. We learned on the second page of notes that carbon
atoms having three bonds or fewer are specifically not chiral centers:

(E)-2-butene

3. Draw any alkane whose H1 NMR spectrum would contain only 1 signal (a singlet) and whose
C13 spectrum (broadband decoupled) would contain 2 signals.

Many possibilities:

4. Explain why the -OH IR peak of CH3CH2OH (gas phase) comes at a higher wavenumber than
the -OH IR peak of CH3CH2OH (liquid phase).

The fact that -OH can come at higher or lower wavenumbers was covered in BOTH notes
and textbook. More hydrogen bonding of the -OH groups correlates with lower
wavenumber. Hence, the gas phase molecule must have less hydrogen bonding. Hey, this
is consistent with what we learned in Chapter 1 notes!! [Section of boiling – liquid to vapor
transition . . . CH1b notes . . . but again even if you didn’t remember this you got the
correct answer because of CH7 notes, OR, CH7 textbook].

5. Draw the structure for the isomer of C4H8O2 having the following H1 NMR data: 3.4 ppm (q,
2H); 2.2 ppm (s, 3H); 1.1 ppm (t, 3H). The IR spectrum of this compound exhibits at strong
absorption at 1715 cm-1. (Hint: pay close attention to the chemical shift of the methylene)
6. Draw the Fischer projection for (2R,3R)-2,3-dibromopentane.

7. Draw a structural isomer of (2R,3R)-2,3-dibromopentane.

8. 1.0 g of a mixture containing only 90% (R)-2-iodopentane and 10% (S)-2-iodopentane is

dissolved in 10.0 mL hexane, and the resulting solution is placed in a polarimeter tube 1.0 dm in
length. What is the observed rotation? The specific rotation of pure (R)-(+)-2-iodopentane is
+2.0 degrees (degrees * mL / g / dm).

e.e. = 90% - 10% = 80% = []mix * 100% / []major = []mix * 100% / +2.0 degrees
[]mix = + 1.6 degrees
 = []*c*l ;  = + 1.6 degrees * mL / g / dm * 1.0 g / 10.0 mL * 1.0 dm = +0.16 degrees

9. A mixture containing only (R)-alanine and (S)-alanine (mixture is known to have more (R)-
than (S)- enantiomer) has an enantiomeric excess of 40% and a specific rotation of +2.0 degrees
(degrees * mL / g / dm). A different mixture of only (R)- and (S)-alanine having a specific
rotation of -1.0 degree (degrees * mL / g / dm) would contain what percentage of (R)-alanine?

e.e. = 40% = []mix * 100% / []major = +2.0 degrees * 100% / []major

[]major = []R +5.0 degrees
e.e. (different) = -1.0 degrees * 100% / -5.0 degrees = 20% (60% S, 40% R)
40% (R)-alanine

10. Draw any meso compound which would contain only one signal in a broadband decoupled
C13 NMR spectrum.

MANY possibilities:

11. The two H atoms on C2 (the middle carbon) of the molecule 1-chloropropane are:
a. homotopic
b. enantiotopic
c. diastereotopic
d. heterotopic
e. none of the above