Practice Problem Set
Iverson CH320N
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1
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Chemistry 320N
Dr. Brent Iverson
Practice Homework
March 22, 2015
Practice Problem Set
Iverson CH320N
Do Not Turn In
Complete the mechanism for the following reaction. Be sure to show arrows to indicate movement of
all electrons, write all lone pairs, all formal charges, and all the products for each step. Remember, I
said all the products for each step. IF A NEW CHIRAL CENTER IS CREATED IN AN
INTERMEDIATE OR PRODUCT, MARK IT WITH AN ASTERISK AS RACEMIC IF
RELEVANT. In the box provided adjacent to each arrow, write the kind of mechanistic element you
used ("make a bond", "add a proton" etc.).
Grignard Reacting with Esters
O
O
MgBr
MgBr
Chemist Opens Flask
H
2)
O
H
H
(mild)
This is an example of Mechanism
followed by Mechanism
Products
2
Practice Problem Set
Iverson CH320N
Do Not Turn In
Complete the mechanism for the following reaction. Be sure to show arrows to indicate movement of
all electrons, write all lone pairs, all formal charges, and all the products for each step. Remember, I
said all the products for each step. IF A NEW CHIRAL CENTER IS CREATED IN AN
INTERMEDIATE OR PRODUCT, MARK IT WITH AN ASTERISK AS RACEMIC IF
RELEVANT. In the box provided adjacent to each arrow, write the kind of mechanistic element you
used ("make a bond", "add a proton" etc.).
α-Halogenation of an Aldehyde or Ketone Catalyzed by Acid
O
O
H
H
H 3C
O
CH 3
C
H
H
O
H 3C
Br
Br
O
H
O
CH 3
Products
3
O
Practice Problem Set
Iverson CH320N
Do Not Turn In
Complete the mechanism for the following reaction. Be sure to show arrows to indicate movement of
all electrons, write all lone pairs, all formal charges, and all the products for each step. Remember, I
said all the products for each step. IF A NEW CHIRAL CENTER IS CREATED IN AN
INTERMEDIATE OR PRODUCT, MARK IT WITH AN ASTERISK AS RACEMIC IF
RELEVANT. In the box provided adjacent to each arrow, write the kind of mechanistic element you
used ("make a bond", "add a proton" etc.).
Reduction of Esters with LiAlH4
O
O
Li
H
H
Al
H
H
Li
H
H
Al
H
H
Chemist Opens Flask
2)
This is an example of Mechanism
O
H
H
followed by Mechanism
Products
4
Practice Problem Set
Iverson CH320N
Do Not Turn In
Fill in the box with the product or products that are missing from the following chemical reaction
equations. When a racemic mixture is formed, you must write "racemic" under both structures
EVEN THOUGH YOU DREW BOTH STRUCTURES.
1) CO2
HO
O
2) HCl / H2O
SOCl2
2 NH3
OH
CuLi
2
1) LiAlH4
1)
2) H2O
2) H2O
1)
2
MgBr
2) HCl / H2O
O
O
H2NNH2
heat
HO
5
H2SO4
(no H2O)
Practice Problem Set
Iverson CH320N
Do Not Turn In
Fill in the box with the product or products that are missing from the following chemical reaction
equations. When a racemic mixture is formed, you must write "racemic" under both structures
EVEN THOUGH YOU DREW BOTH STRUCTURES.
O
O
2 NH2CH3
O
O
1) NaBH 4
2) H2O
1) 2 BrMg
O
2) HCl / H2O
O
CuLi
1)
2
Cl
2) H2O
O
O
O
1) DIBAL-H
2) H2O
6
Practice Problem Set
Iverson CH320N
Do Not Turn In
Using any reagents turn the starting material into the indicated product. All carbon atoms must come from
the starting material. Draw all molecules synthesized along the way. When it doubt, draw the molecule!
Hint: this should look familiar as a homework problem.
All of the carbons of the produce must come from the given starting material.
(13 pts)
?
OH
OH
7