orgo I exam 3
Exam 3-Take Home
Chem 241A Organic Chemistry
Sections 5 & 6
Dr. Pyun
Due in Class: November 7th, 2007
You are allowed to use the McMurry Organic Chemistry Text, Solution
Manual and Lecture Notes to answer the following questions. You will be expected to complete this assignment on your own. Do not work in groups, or seek outside assistance from tutors, TA, or faculty. You will receive zero points for the exam if you are found utilizing other resources. Name:
Problem 1)
(8)
Problem 2)
(20)
Problem 3)
(8)
Problem 4)
(8)
Problem 5)
(20)
Problem 6)
(12)
Total:
(76)
1) Provide the IUPAC, or common names for the following compounds. Be sure to indicate the appropriate stereochemistry where necessary (2 pts each, 8 pts total).
H
(a)
CH3
Br
CH 3
(b)
(c)
Cl
H3 C
H
(d)
CH3
CH 3
H 3C
H
2) write out the mechanism of the below reaction using curved arrow notation. Be sure to include every step in this reaction. (20 pts)
3. The following polymers were prepared using benzoyl peroxide as the initiator for free radical polymerization. Write out the chemical skeletal structures of the monomers used to prepare each polymer. (2 pts each, 8 pts total)
O
CH3
O
CH2 C
O
H n O
(a)
O
H
O
O
CH2 C
O
O
n
O
(b)
O
H
O
O
CH2 C
O
n
C
(c)
N
O
H
O
CH2 C
O
O
n
(d)
Cl
4. Write in chemical skeletal structures of reactants or products for the following reactions: (8 pts)
H
O
H
mCPBA
CH 3
H
O
CH 3
mCPBA
H 3 CH 2C
H
OsO4, NMO
O
HIO4, H2O
THF
H
O
5. Starting with acetylene, devise a reasonable synthesis using the reactions covered in class to this point to prepare (4R, 5R)-4,5-dibromooctane. Show all reaction steps, reactants, reagents, intermediate compounds and products (not mechanism). (20 pts)
6a) Show all of the products, including all
Chem 241A Organic Chemistry
Sections 5 & 6
Dr. Pyun
Due in Class: November 7th, 2007
You are allowed to use the McMurry Organic Chemistry Text, Solution
Manual and Lecture Notes to answer the following questions. You will be expected to complete this assignment on your own. Do not work in groups, or seek outside assistance from tutors, TA, or faculty. You will receive zero points for the exam if you are found utilizing other resources. Name:
Problem 1)
(8)
Problem 2)
(20)
Problem 3)
(8)
Problem 4)
(8)
Problem 5)
(20)
Problem 6)
(12)
Total:
(76)
1) Provide the IUPAC, or common names for the following compounds. Be sure to indicate the appropriate stereochemistry where necessary (2 pts each, 8 pts total).
H
(a)
CH3
Br
CH 3
(b)
(c)
Cl
H3 C
H
(d)
CH3
CH 3
H 3C
H
2) write out the mechanism of the below reaction using curved arrow notation. Be sure to include every step in this reaction. (20 pts)
3. The following polymers were prepared using benzoyl peroxide as the initiator for free radical polymerization. Write out the chemical skeletal structures of the monomers used to prepare each polymer. (2 pts each, 8 pts total)
O
CH3
O
CH2 C
O
H n O
(a)
O
H
O
O
CH2 C
O
O
n
O
(b)
O
H
O
O
CH2 C
O
n
C
(c)
N
O
H
O
CH2 C
O
O
n
(d)
Cl
4. Write in chemical skeletal structures of reactants or products for the following reactions: (8 pts)
H
O
H
mCPBA
CH 3
H
O
CH 3
mCPBA
H 3 CH 2C
H
OsO4, NMO
O
HIO4, H2O
THF
H
O
5. Starting with acetylene, devise a reasonable synthesis using the reactions covered in class to this point to prepare (4R, 5R)-4,5-dibromooctane. Show all reaction steps, reactants, reagents, intermediate compounds and products (not mechanism). (20 pts)
6a) Show all of the products, including all