CHM 235, Fall 2014
Homework Assignment 4 (25pts.)
Due in class November 20, 2014
(NO LATE ASSIGNMENTS ACCEPTED!)
the free radicals (I-III) shown below in order of decreasing stability (i.e., from
most stable to least stable).
(CH3)3C·, CH2CHCH2·, CH3CH2·, CH3·, (CH3)2CH·
H atom in the molecule shown will be most readily abstracted by a bromine
radical? Explain your answer to get credit.
3. Complete each of the equations wtth the structure of the possible monohalogenated
products. Circle the major product. Show the detailed mechanism for its formation.
4. Draw the structures of the two major products formed in the following reaction:
Show the detailed mechanism for the formation of each product.
5. Which of the following compounds is the most nucleophilic? Explain your answer to
6. List the following bromides in order of their increasing reactivity as substrates in SN2
reactions: PhBr, PhCH2Br, and PhCH(CH3)Br. Explain your answer to get credit.
7. List the following alkyl halides in order of their increasing reactivity as substrates in
SN2 reactions: 2-chlorobutane, 2-iodobutane, and 1-iodobutane. Explain your answer to
8. Rank the following molecules in order of increasing relative rate of SN1 solvolysis
with methanol and heat (slowest to fastest reacting). Explain your answer to get credit.
9. Arrange the following carbocations in order of their decreasing stabilities (most stable
10. Name the given alkyl halides
11. Propose a detailed step-by-step mechanism for the formation of all possible
substitution products in each of the given reactions. Circle the major product.