,
CHEM 222 Homework for Chapter 9, Alkynes
1. Give the name or draw the structure for each of the following compounds.
Br
CH3
4-isopropyl-6-methoxy-5-methylhept-1-yne (E)-3-methylhex-4-en-1-yne (E)-3,6-dimethylocta-4-en-1,7-diyne
2. Rank the acidity of the following compounds (1 = most acidic)
H
OH N
H
H
3-methylbut-1-yne hexan-3-ol 3-methylbut-1-ene piperidine
O
OH OH
H
OH
O2N
isobutane
p-cresol 4-nitrophenol
benzoic acid
3. There are eight structures in Problem 2. Make the conjugate base of four of them and show favorable
deprotonation reactions with the other four. You will use all eight compounds to write four favorable acid-base
reactions. Add arrows to show the movement of the electrons in these chemical reactions.
4. Show a complete mechanism for the following reaction. With arrows, of course. Then predict the most prevalent
minor product that you would expect.
N
H
Br
Li
(LDA)
CHEM 222 Homework for Chapter 9, Alkynes
1. Give the name or draw the structure for each of the following compounds.
Br
CH3
4-isopropyl-6-methoxy-5-methylhept-1-yne (E)-3-methylhex-4-en-1-yne (E)-3,6-dimethylocta-4-en-1,7-diyne
2. Rank the acidity of the following compounds (1 = most acidic)
H
OH N
H
H
3-methylbut-1-yne hexan-3-ol 3-methylbut-1-ene piperidine
O
OH OH
H
OH
O2N
isobutane
p-cresol 4-nitrophenol
benzoic acid
3. There are eight structures in Problem 2. Make the conjugate base of four of them and show favorable
deprotonation reactions with the other four. You will use all eight compounds to write four favorable acid-base
reactions. Add arrows to show the movement of the electrons in these chemical reactions.
4. Show a complete mechanism for the following reaction. With arrows, of course. Then predict the most prevalent
minor product that you would expect.
N
H
Br
Li
(LDA)
