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Alcohol Reacions and Comnformations of Cyclic Alcohols

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Please see the attached file for diagrams.
1. Choose the best reagent for carrying out the following reactions from the list
below. Place the letter of the reagent(s) in the box over the reaction arrow.
Only one letter per box (10 points).

a. NaH, then CH3I
b. NaOCH3, CH3OH
c. m-ClC6H4CO3H
d. CH3MgBr in ether, then H3O+
e. warm H2SO4/H2O
f. Hg(O2CCF3)2, CH3OH
g. H2/Pd
h. PCC, CH2Cl2
i. Cl2, H2O
j. LiAlH4 in ether, then H3O+

2. To answer the following questions, consider the reaction below
a. Draw both chair conformations of the alcohol product on the templates provided below. Circle the least stable conformation.

b. Provide the IUPAC name for the product alcohol.

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Solution Summary

A reaction pathway involving alcohols is solved and conformations of cyclic alcohols are discussed.

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1. Choose the best reagent for carrying out the following reactions from the list
below. Place the letter of the reagent(s) in the box over the reaction arrow.
Only one letter per box (10 points).

a. NaH, then CH3I
b. NaOCH3, CH3OH
c. m-ClC6H4CO3H
d. CH3MgBr in ether, then ...

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