ETHERS&THIOLS SOLUTIONS
Don’t forget to study the generic functional groups and the common alkyl groups (neopentyl, etc.)
1. Give the IUPAC (I) and where possible the common (c) names for the following:
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ETHERS&THIOLS SOLUTIONS
a)
4-methoxycyclohexene
b)
(c) allyl vinyl ether
c)
2-ethylfuran
d)
(c) benzyl phenyl sulfide
(I) (phenylthio)toluene
(I) phenyl(phenylthio)methane
e)
(I) (isopropylthio)cyclopentane
(I) (1-methylethylthio)cyclopentane
(c) cyclopentyl isopropyl sulfide
f)
oxetane
g)
(I) 3-mercapto-2-methyl-1-propanol
(I) 2-methyl-3-thio-1-propanol
h)
3-bromopyran
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ETHERS&THIOLS SOLUTIONS
2. Draw structures of the following:
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ETHERS&THIOLS SOLUTIONS
a) isopropyl neohexyl ether
b) tetrahydrothiophene
c) 9-crown-3 ether
d) di(p-chlorophenyl) ether
e) 1,3-(dimethylthio)benzene
f) isobutyl mercaptan
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ETHERS&THIOLS SOLUTIONS
3. Draw structures of the following
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ETHERS&THIOLS SOLUTIONS
a) 2-mercaptobenzoic acid
b) 2,2-diethoxybutane
c) 3-(ethylthio)cyclopentene
d) isopropyl tert-butyl ether
e) neopentyl mercaptan
f) p-methoxyanisole
g) ethyl m-tolyl ether
h) thiopyran
i) tetrahydrofuran
j) sec-butyl phenyl sulfide
k) t-amyl isohexyl ether
l) 12-crown-4 ether
m) diphenyl sulfide
n) 2-pentanethiol
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ETHERS&THIOLS SOLUTIONS
4. Give the IUPAC (I) and where possible the common (c) names for the following
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ETHERS&THIOLS SOLUTIONS
a)
2-methoxyoxetane
b)
1,4-dioxane
c)
oxirane
or
ethylene oxide
d)
dimethyl sulfoxide
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ETHERS&THIOLS SOLUTIONS
5. Draw the full mechanism (using arrows) and write products of the Williamson Ether synthesis with sodium methoxide and ethyl bromide. Name the type of mechanism and name the product
6. Write equations, showing all reagents required to produce the following compounds using Williamson type synthesis. Include the intermediate products (mechanism and transition states not required). Hint: each one requires two steps.
a) (1 of the reagents must contain an -OH group)
b) (1 of the reagents must contain an -SH group)
c) (1 of the reagents must contain an -OH group)
7. Write the products of the following reactions. No mechanisms required
a)
b)
c)
d)
e)
f)
g)
8. Remember to think backwards as well as forwards.
a)
b)
c)
9. Write the products of the following reactions. No mechanisms required
a)
b)
c)
d)
10. Write equations showing how the following transformations can be carried out. No mechanisms required but show all reagents and intermediate products formed. More than one step may be necessary
a)
b)
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