Name______________________________________________________ SN_____

Alcohols
Instructions: Consider the Grignard reaction below to answer the following question(s).

1 Refer to instructions. The electrophile in this reaction is indicated by letter _____.

Instructions: Draw structures corresponding to each of the following IUPAC names.

2. Draw:

cyclopropyl ethyl sulfide

3. Draw:

Dicyclohexyl sulfide

Instructions: Provide correct IUPAC names for each of the structures below.

4. Name:

5. Name:

Instructions: Consider the reaction below to answer the following question.

6. Refer to instructions. On the structures provided below draw arrows showing the mechanism of step two of
this reaction.
 Instructions:

Give the major organic product(s) of the following reactions or sequences of reactions. Show all relevant
stereochemistry.

7. Write the product(s):

8. Write the product(s):

9. Write the product(s):

10. Write the product(s):

11. Write the product(s):

Instructions:
Choose the best reagent(s) for carrying out the following conversions from the list provided below. Place the
letter of the best choice in the blank. Reagents may be used more than once.

a. CrO3, H2SO4, H2O

b. 1. NaBH4, ethanol
2. H3O+
c. 1. LiAl4, ether
 2. H3O+
d. periodinane

12. Refer to instructions. _____

13. Refer to instructions. _____

Instructions: Consider the Grignard reaction below to answer the following question(s).

____ 14. Refer to instructions. If a secondary alcohol were desired as a product of the reaction, B should be replaced
with
a. an ester
b. an aldehyde
c. formaldehyde (methanal)
d. a primary alcohol

Instructions: Consider the reaction below to answer the following question.

____ 15 Refer to instructions. Mechanistically, the Williamson ether synthesis outlined above is:
a. an E1 process
b. an SN1 process
c. an E2 process
d. an SN2 process

____ 16. Which of the following would not react with either Na 2Cr2O7 or periodinane?
 1 2 3 4

a. only 1
b. only 3
c. only 2 and 4
d. 1, 2, 3 and 4

____ 17. Which of the following are ethers?

1 2 3 4

a. only 1 and 2
b. only 1 and 4
c. only 1, 2 and 3
d. all of these are ethers

____ 18. What is the IUPAC name of the following compound?

a. ethyl isopropyl thiol

b. 2-methylsulfanylpropane
c. ethyl isopropyl disulfide
d. ethyl isopropyl sulfide