Chapter 10: PROBLEM 10.49 (page 422)
Question: Draw the constitutional isomer formed in each reaction.
a.

b.

c.

d.

e.

f.

Short Answer
Answer
a.

b.

c.

d.

e.

f.

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Chapter 10: PROBLEM 10.49 (page 422)
Question: Draw the constitutional isomer formed in each reaction.
a.

b.

c.

d.

e.

f.

Answer
a.

b.

c.

d.

e.

f.

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Question: Which alcohols can be prepared as a single product by hydroboration–oxidation of an alkene? Which alcohols can be prepared as a single product by the acid-catalyzed addition of H2O to an alkene?
a.

b.

c.

d.

Question: When buta-1,3-diene (CH2=CH-CH=CH2) is treated with HBr, two constitutional isomers are formed CH3CHBr-CH=CH2and Br-CH2CH=CHCH2. Draw a stepwise mechanism that accounts for the formation of both products.
Question: Give the structure corresponding to each name.
a. (E)-4-ethylhept-3-ene
b. 3,3-dimethylcyclopentene
c. 4-vinylcyclopentene
d. (Z)-3-isopropylhept-2-ene
e. cis-3,4-dimethylcyclopentene
f. 1-isopropyl-4-propylcyclohexene
g. 3,4-dimethylcyclohex-2-enol
h. 3,5-diethylhex-5-en-3-ol
Question: Explain why the addition of HBr to alkenes A and C is regioselective, forming addition products B and D, respectively.

Question: Draw the products formed when each alkene is treated with followed by . Include the stereochemistry at all stereogenic centers.
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