CHM207 (ORGANIC CHEMISTRY )

TUTORIAL 6
CHAPTER 6: HYDROXYL COMPOUNDS
1. Write the structural formulae of the following alcohols and classify them as
primary, secondary or tertiary alcohols.
a) 2-methyl-1-propanol
b) 2-methyl-2-propanol
c) 4-penten-2-ol
d) 1-chloro-3,3-dimethyl-2-butanol
e) 2,2-dimethyl-1-butanol
f) benzyl alcohol
g) 3-chloro-5-phenyl-1-hexanol
h) 1,3-diphenyl-2-propanol

2. Name the following alcohols:

a) CH3CH2CH(OH)CH3
b) H
OH
c) CH3CHBrC(CH3)2OH
d) CH3

OH

e) OH
Cl

Cl

f) HOCH2CH2CH2CH2OH

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g) OH

HO OH

h)
OH
Cl CH2CH3

i)
OH

j) OH

CH3

k) OH
CH2CH2CCH3
CH3

3. Predict which members of each pair have higher boiling points. Explain
your answers.
a) 1-hexanol or 3,3-dimethyl-1-butanol
b) 2-hexanol or 2-hexene
c) 2-hexanol or 1,5-hexanadiol

4. Predict which member of each pair will be more soluble in water. Explain
the reasons for your answers.
a) 1-hexanol or cyclohexanol
b) 1-heptanol or 4-methylphenol
c) 3-ethyl-3-hexanol or 2-octanol
d) 2-hexanol or cyclooctane-1,4-diol

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5. Predict which member of each pair will be more acidic. Explain your
answers.
a) methanol or t-butyl alcohol

b) 1-chloroethanol or 2-chloroethanol
c) 2-chloroethanol or 2,2-dichloroethanol

6. Give the products for the following reactions:

a) 1-propanol + Na
b) p-chlorophenol + NaOH
c) 1-butanol + K2Cr2O7/H+
d) 1-pentanol H+

e) t-butyl alcohol + HCl

f) 1-phenylethanol + SOCl2
g) Allyl alcohol + HCl (aq)
+
h) CH3CH2CH2COOH + CH3OH H
PCC
i) CH3CH2CH2OH

7. Predict the reactants for each of the following reactions.

a) Cl
SOCl2
?

Na (s)
b) ? CH3CH2CH2O-Na+ + 1/2 H2

O
+
c) KMnO4/H CH3CH2CCHCH3
?
CH3

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 CHM207 (ORGANIC CHEMISTRY )

d) O O
H+
C OH + ? C OCH2CH3

e) CH3
PCC
? CH3CHCHO

8. Show how you would make each compound. Give the starting materials,
products and reagents.
a) t-butyl alcohol from isobutylene
b) 1-phenylethanol from styrene
c) p-nitrophenol from phenol
d) O OH

from

e) CH3CH2CH2Cl from CH3CH2CH2-OH

9. Predict the major and minor products of dehydration catalyzed by sulfuric

acid.
a) 2-methyl-2-butanol
b) 1-pentanol
c) 2-pentanol
d) 2-methylcyclohexanol

10. Identify whether each of the following alcohols give(s) yellow precipitate
when tested with iodoform reagent. Write the chemical equation if the
reaction gave the positive result.
a) 1-propanol
b) 2-propanol
c) 2-methyl-2-propanol

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11. Give the structures A to E:

H2O/H+

H+ OH PBr3 NH3
D B C

Na2Cr2O7
H2SO4