ALCOHOLS & PHENOLS SOLUTIONS

Don’t forget to study the generic functional groups and the common alkyl groups (isobutyl, etc).

  1. IUPAC = I and common = c.

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ALCOHOLS & PHENOLS SOLUTIONS

a)
6-methyl-4-propyl-3-heptanol
(this is the longest chain containing
the -C and with the most branch
points)

b)
4-cyclopentyl-2,2-butanediol

c)
(Z)-4-methyl-2-cyclohexen-1-ol
or
cis-4-methyl-2-cyclohexen-1-ol

d)
4-isopropyl-2-methylphenol

e)
phenylmethanol (I)
benzyl alcohol (c)

f)
3-penten-2-ol

g)
2-cyclopenten-1-ol

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ALCOHOLS & PHENOLS SOLUTIONS

  1. Draw structures of the following compounds:

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ALCOHOLS & PHENOLS SOLUTIONS

a)glycerol
(also glycerin or 1,2,3-propanetriol)

b)m-cresol

c)resorcinol

d)hydroquinone

e)-naphthol

f)allyl alcohol

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ALCOHOLS & PHENOLS SOLUTIONS

  1. Give IUPAC names and, where possible, common names for the following compounds.

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ALCOHOLS & PHENOLS SOLUTIONS

a)
3-(1-ethyl-3-methylbutyl)phenol

b)
5-bromo-1,2-hexanediol

c)
isobutyl alcohol (c)
2-methyl-1-propanol (I)

d)
(c) sec-butyl alcohol
(I) 2-butanol

e)
(c) t-butyl alcohol
(c) 2-methyl-2-propanol

f)
catechol (c)
1,2-dihydroxybenzene (I)
2-hydroxyphenol (I)

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ALCOHOLS & PHENOLS SOLUTIONS

  1. Draw structures of the following compounds

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ALCOHOLS & PHENOLS SOLUTIONS

a)isoamyl alcohol

b)1-cyclopentyl-1-phenyl-2-propanol

c)cis-2-iodocyclohexanol

d)2-ethyl-2-buten-1-ol

e)trans-2-ethyl-3-methyl-2-penten-1-ol

f)(E)-1-chloro-1,2-cyclobutanediol

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ALCOHOLS & PHENOLS SOLUTIONS

  1. Note that this is a 3° alcohol.

a)

b)

c)

d)

e)

  1. What Grignard and what carbonyl will react to produce the following. Draw structures of all possible combinations.
  2. What hydride and what carbonyl will react to produce the following. Draw structures of all possible combinations.

  1. List the reagents needed for the following transformations

a)

b)

c)

d)

e)

f)

g)

  1. Number the following compounds in order of acidity, i.e., 1 = most acidic, 4 = least acidic

  1. The shortest routes are shown below. In some cases, other, longer synthetic routes are possible.

a)

b)

c)

  1. This one is tougher. Note the addition of the ethyl group. The only methods we’ve learned for adding Carbon groups are 1) chain lengthening terminal alkynes, 2) FC alkylations/acylations to aromatics, 3) Grignards, organosodium and Gilman reactions. Obviously the first two don’t apply here, so look for an opportunity to perform a Grignard rxn, i.e., synthesize a carbonyl to add the Grignard to:
  2. For the following reaction:

a)Write products for the reaction

b)Show the mechanism of the reaction

c)Calculate pKeq

  1. This 3° alcohol is undergoing an SN1 reaction. OH is a poor leaving group, but once protonated by a strong acid, a better leaving group is formed (H2O).

  1. Remember to consider whether the substrate is 1°, 2°, or 3°

a)

b)

c)

d)

e)

f)

g)

h)

i)

  1. Draw the structures of a Grignard and a carbonyl compound that can be used to synthesize the following alcohols. Show all possible combinations.
    Also draw the structures of any carbonyl compounds that can be reduced by a LiAlH4 to prepare these compounds

a)

b)

  1. Write equations to show how the following transformations can be carried out. More than one step may be required. Show all reagents and the products of each step, but do not show any transition states. Mechanisms are not required

a)

b)

c)

  1. .
  2. Draw the structure(s) of all reagents which would give the following alcohol when reduced with LiAlH4
  3. Draw the structures of all sets of reagents that would give the following alcohol when reduced with a Grignard reagent. Show Grignards as well as other reagents.
  4. Draw the formulas or structures of the products of the following reactions ...

a)

b)

c)

d)


  2. Remember to think backwards from the product as well as forwards from the reagent.

a)

b)

c)

d)

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