Download CHEM 2411 – Organic Chemistry I Radicals/Radical Reactions 1

CHEM 2411 – Organic Chemistry I
Radicals/Radical Reactions
1) Rank the following radicals in order of decreasing stability (most stable to least stable).
A)
B)
C)
D)
E)
IV > I > II > III
III > I > II > IV
III > II > I > IV
III > IV > II > I
II > I > III > IV
2) Using correct arrow formalism, draw all of the reasonable resonance structures for the radical shown below.
3) Which of the labeled C-H bonds is the weakest?
A)
B)
C)
D)
E)
C-Ha
C-Hb
C-Hc
C-Hd
C-He
4) Use correct arrow formalism to show the mechanism of the following radical process:
+
5) Which of the following is an example of termination?
6) Predict the major product(s) of the following reaction:
7) Which of the following is the correct name for the major product of the following reaction?
A)
B)
C)
D)
E)
(R)-3-bromo-3-ethylbutane
(S)-3-bromo-3-ethylbutane
(R)-3-bromo-3-methylpentane
(S)-3-bromo-3-methylpentane
3-bromo-3-methylpentane
8)
9) Draw the major product(s) of the following reaction. Is the product optically active? Explain.
10) Upon treatment of 1-methylcyclopentene with NBS and irradiation with UV light, exactly
nine compounds (including stereoisomers) are formed. Draw all nine products.
11) Upon treatment with NBS and irradiation with UV light, 2-methyl-2-butene reacts to
produce exactly six monobrominated compounds. Draw the products of this reaction.
12) What C5H12 isomer will give only a single monochlorination product?