Chem 215-216 HH W11 - Quiz 1: January 14, 2011 Name_________Key_____________

Lab: Mon; Tue; Wed; Fri (circle one that applies) GSI: Alex; Justin; Alina; Laura (circle one that applies)
I. (14 points) Identify the indicated pairs of hydrogens in each of the following compounds as (i) homotopic,
(ii) enantiotopic, or (iii) diastereotopic H’s. Write the answers as (i), (ii), or (iii). Also write the number of
unique H’s and C’s for each compound.
Homotopic, enantiotopic, or diastereotopic?
How many unique H's and C's?
(a) (b) O Hc CH3
O Ha
Hb H c
H Ha
O O
(i)
Ha and Hb: _______
(iii)
Ha and Hb: _______ Hb
H 3N H H H
d (i) O
H Hc and Hd: _______ Hd CH3 (i)
Hc and Hd: _______
7
Number of unique H's: ________ 3
Number of unique H's: ________
7
Number of unique C's: _________ 4
Number of unique C's: _________

(c) (iii) (ii)

H3C O O CH3 Ha and Hb: _______ Hb and Hd: _______

(ii)
Ha and Hc: _______ (iii)
Ha and Hd: _______
Ha Hb H Hc Hd
O
CH3 5
Number of unique H's: ________
5
Number of unique C's: _________

II. (6 points) For each of the following pairs of compounds, match the expected IR wave numbers with the
compounds.
(a) For vC=O: 1720 or 1695 cm-1 (b) For vC≡C or vC=C: 2150 or 1640 cm-1

O O
H
CH3 CH3 C C C CH3
C CH3
H

1720 cm-1 1695 cm-1 1640 cm-1 2150 cm-1

(c) For the vC-H of the indicated C-H bonds:

3200 or 2950 cm-1

H
C C H
H

2950 cm-1 3200 cm-1