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Tutorial 6

This document provides a tutorial on hydroxyl compounds (alcohols) in organic chemistry. It contains 11 questions covering topics such as: 1) Drawing structural formulas and classifying alcohols as primary, secondary or tertiary 2) Naming alcohols given structural formulas 3) Predicting boiling points and solubility based on alcohol structure 4) Predicting acidity and drawing reaction products 5) Drawing synthesis routes for alcohols from starting materials 6) Predicting dehydration and iodoform test reaction products

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Eqieyn Jerr
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216 views

Tutorial 6

This document provides a tutorial on hydroxyl compounds (alcohols) in organic chemistry. It contains 11 questions covering topics such as: 1) Drawing structural formulas and classifying alcohols as primary, secondary or tertiary 2) Naming alcohols given structural formulas 3) Predicting boiling points and solubility based on alcohol structure 4) Predicting acidity and drawing reaction products 5) Drawing synthesis routes for alcohols from starting materials 6) Predicting dehydration and iodoform test reaction products

Uploaded by

Eqieyn Jerr
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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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

CHM207 (ORGANIC CHEMISTRY )

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 hexane-1,5-diol

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

CHM207 (ORGANIC CHEMISTRY )

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+

heat

e) t-butyl alcohol + HCl


f) 1-phenylethanol + SOCl2
g) 3-methyl-2-pentanol + PBr3 (aq)
+
h) CH3CH2CH2COOH + CH3OH H

i) CH3CH2CH2OH

7.

PCC

Predict the reactants for each of the following reactions.


a)

Cl
?

b)

SOCl2

Na (s)

CH3CH2CH2O-Na+ + 1/2 H2

O
c)

KMnO4/H
heat

CH3CH2CCHCH3
CH3

CHM207 (ORGANIC CHEMISTRY )

d)

C OH

e)

O
C OCH2CH3

CH3

PCC

?
8.

H+

CH3CHCHO

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)

OH
from

e) CH3CH2CH2Cl

9.

from

CH3CH2CH2-OH

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

CHM207 (ORGANIC CHEMISTRY )

What test or analysis can be done to distinguish the above alcohols? Give
the reagent used and the observations.

11.

Give the structures A to E:


A
H2O/H+

OH

H+

PBr3

Na2Cr2O7
H2SO4

NH3

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