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Problem 51
What is the structural relationship between a thiol and an alcohol?
Problem 53
Oxidation of a dithiol such as 2,5-hexanedithiol forms a six-membered ring containing a disulfide group as part of the ring. Draw the structure of this cyclic disulfide (Hint: Draw the starting compound in line structure format first).
Problem 54
The boiling point of propanol is 97 °C ,much higher than that of either ethanethiol (37 °C) or chloroethane (13 °C) , even though all three compounds have similar MWs. Explain.
Problem 55
Propanol is very soluble in water, but ethanethiol and chloroethane are only slightly soluble. Explain.
Problem 56b
Define the following terms:
b. Achiral
Problem 56c
Define the following terms:
c. Chiral carbon
Problem 58a
Identify the chiral center(s) in each of the following molecules:
a. 2-Methyl-3-pentanol
Problem 59d
Are the following molecules chiral or achiral? If they are chiral, identify the chiral carbon atom(s).
d.
Problem 60
Name all unbranched ether and alcohol isomers with formula C5H12O and write their structural formulas.
Problem 63
Phenols undergo the same kind of substitution reactions that other aromatic compounds do. Formulate the reaction of p-methylphenol with Br2 to give a mixture of two substitution products.
Problem 66f
Which of the alcohols pictured in Problem 14.48 are chiral? Indicate the chiral carbons for those that are chiral.
a.
b.
c. 2,3-Pentanediol
d.
e.
f.
Problem 67a
Write the formulas and IUPAC names for the following common alcohols.
a. Rubbing alcohol
Problem 67d
Write the formulas and IUPAC names for the following common alcohols.
d. Diol used as antifreeze (two answers)
Problem 68c,d
Name the following compounds:
c.
d.
Problem 68e,f
Name the following compounds:
e.
f.
Problem 71
'Designer vinegars' have become very popular over the past decade. Vinegars made from champagne, merlot, and other wines are but a few of these. All wines contain ethanol, and these vinegars are simply wines containing microorganisms that have caused oxidation of the ethanol present. If vinegar is simply ethanol that has been oxidized, what is the structure of the acid formed?
Problem 73a
Draw all possible cyclic C7H14O alcohol isomers having a cyclohexane ring and a methyl group. (Hint: Adapt the method described in Worked Example 12.12 to arrive at your answers.)
Problem 73b
Identify all chiral centers in the isomers that you drew for part (a).
Problem 74
Using the alcohol shown, draw all the possible alkenes that might be formed on its dehydration. Which do you think will be the major product(s)? Which do you think will be the minor product(s)? It is alright to have more than one major and minor product.
Problem 75
Using the alcohol shown, draw all the possible alkenes that might be formed on its dehydration. Which alkenes can exist as cis–trans isomers? Draw them, in both condensed and line structure, and identify each as cis or trans. Explain your choices.
