Our Lady College of the Salvatorian Sisters – Abra
Chemistry
Worksheet 5
Name: Class: LS
Title: Chapter 11: Carboxylic acid Date: January 2024
Exercise 1: Identification of an Ester and kinetics of Esterification
A saturated mono alcohol (A): CxHyO has the following mass percent composition:
C = 60% H = 13.33%
A. Molecular formula of an alcohol (A)
1. Show that the molecular formula of (A) is C3H8O.
2. Write the condensed structural formula of a functional isomer of (A).
B. Mild oxidation of (A)
The alcohol (A) is mixed with excess potassium permanganate solution. The reaction is
represented by the following equation:
5 C3H8O + 4 MnO4- + 12 H+ 5 CxHyOz + 4 Mn2+ + 11 H2O
1. Determine the molecular formula of (B). Deduce its condensed structural formula.
2. Identify the class, the condensed structural formula and the name of alcohol (A).
3. Complete the missing in the following reaction. Name the missing compound.
Cu
(A) ------------ + ------------
300 ℃
C. Esterification reaction
120 g of the alcohol (A) is introduced with an equimolar amount of (B) into a flask in the
presence of few mL, of concentrated sulfuric acid. The mixture is refluxing for some time
and anti-bombing stones are placed in the reactional mixture.
1. Determine the number of moles of each reactant initially introduced
2. Write the equation of the esterification reaction.
3. Precise the function of:
a) refluxing b) heating
The acid left in the flask is titrated and the results obtained are recorded.
Time (min) 0 3 7 12 20 30 40 50
n acid (mol) 2 1.65 1.27 0.95 0.66 0.5 0.48 0.48
4. Plot the curve n (acid) = f(t)
Take the following scale 1 cm 0.2 mol 1 cm 5 min
5. Determine the composition of the mixture at equilibrium.
6. Deduce the equilibrium constant relative to concentration Kc.
Given: C = 12 H = 1 O = 16 g/mol
Exercise 2: Identification of certain Organic Compounds
The mild oxidation of an alcohol (A) leads to the formation of a monocarboxylic acid (B) with
a saturated open carbon chain. The aim of this exercise is to identify (A) and (B) and to
study their esterification reaction.
Given:
- M(H) = 1 g.mol-1; M(C) = 12 g.mol-1; M(O) = 16 g.mol-1
- The yield of the esterification of an equimolar mixture of carboxylic acid and a primary
alcohol is 67 %.
1. Identification of (A) and (B)
The percentage by mass of oxygen in the acid (B) is 36.36 %.
1.1. Show that the molecular formula of (B) is C4H8O2. Deduce the molecular formula of
(A).
1.2. Knowing that the carbon chain of (A) is branched, identify (A) and (B).
2. Esterification of Alcohol (A)
A mixture of 1 mol of (A) and 2 mol of (B) is heated in the presence of few drops of
concentrated sulfuric acid. After a certain time, a homogeneous equilibrium is established
with a constant KC = 4.
2.1. Write the equation of this reaction. Give the systematic name of the organic
compound (C) formed.
2.2. Determine the number of moles of (C) formed at equilibrium. Deduce the yield of this
esterification.
2.3. This yield exceeds 67 %. Explain, if each one of the three following proposals
justifies this fact:
2.3.1. Heating the reacting medium.
2.3.2. Presence of few drops of sulfuric acid in the reacting medium.
2.3.3. Using an initial mixture of reactants which is not equimolar.
Exercise 3:
1. Given the following organic compound.
1.1. Give the systematic name of each compound.
1.2. Distinguish between (A) and (B), using an appropriate test.
1.3. Write the equation of the reaction that allow preparing (C) from (B).
1.4. Explain why, the mild oxidation of (C) may lead to (B) but not to (D).
2. Esterification:
3-methylbutyl ethanoate is used as aroma of banana in some syrup. The condensed structural
formula of this compound (x) is: CH3 – COO – CH2 – CH2 – CH(CH3)2.
2.1. Give the name of the functional group of this compound.
2.2. Compound (x) is obtained by the reaction between an acid (y) and a primary alcohol
(z).
2.2.1. Write the condensed structural formulas of (y) and (z) and give their names.
2.2.2. Write the equation of the reaction between (y) and (z).
2.2.3. Give the name of this reaction and its characteristics.
3. To prepare this aroma
We mix 0.5 mol of (y) and 0.5 mol of (z) with few mL of sulfuric acid, by an appropriate
method using reflux heating. The evolution of the number of moles of the reactant (y)
denoted ny is determined which makes is possible to draw the curves below.
3.1. Explain why curves 1,2 and 3 do not correspond to the experiment.
3.2. Using the information read on the graph corresponding to the experiment
Performed. Determine the yield of the reaction.
3.3. Does the value of the yield vary?
3.3.1. By extending the heating time.
3.3.2. Increasing the temperature.
3.3.3. Adding more moles of the acid A. Justify your answers.
Exercise 4: Properties of an Alcohol
Alcohols are products with a great industrial and commercial importance. They undergo many
and diverse chemical reactions and are used in the synthesis of many compounds such as
esters.
The aim of this exercise is to study the chemical properties of the alcohol (A) and its
reaction with methanoic acid.
Given: Molar mass in g.mol-1: M (H) = 1; M(C) = 12; M (O) = 16.
1. Chemical properties of the Alcohol (A)
(A) is a saturated and non-cyclic mono-alcohol. The quantitative analysis of alcohol (A) shows
that the percentage by mass of oxygen is %O = 21.62%
1.1. Show that the molecular formula of the alcohol (A) is C4H10O.
1.2. The condensed structural formula of the alcohol (A) is:
1.2.1. Indicate the class of alcohol (A).
1.2.2. Give its systematic name.
1.2.3. Write the condensed structural formulas of the other three alcohol isomers
of alcohol (A).
1.2.4. Justify that the molecule of the alcohol (A) is chiral.
1.2.5. Represent, according to Cram, the two enantiomers of alcohol (A).
1.3. The mild oxidation of the alcohol (A) by a solution of acidified potassium
permanganate leads to the formation of an organic compound (B).
Correct the following propositions:
1.3.1. The systematic name of (B) is butanal.
1.3.2. The compound (B) gives white crystals with 2,4- DNPH.
2. Reaction of the Alcohol (A) With Methanoic Acid
A mixture of 0.2 mol of alcohol (A) and 0.2 mol of methanoic acid is heated to reflux, in the
presence of few drops of concentrated sulfuric acid as a catalyst.
The esterification reaction is represented by the following equation:
methanoic acid + alcohol (A) ⇌ ester (E) + water
At an instant of time t, the equilibrium is reached. The number of moles of methanoic acid
remained at equilibrium is n (acid) = 0.08 mol.
2.1. Write, using the condensed structural formulas, the equation of this
esterification reaction.
2.2. Determine the number of moles of each constituent of the reacting mixture, at
equilibrium.
2.3. Deduce the value of the equilibrium constant Kc.
2.4. The same experiment is carried out again with only one change: “without the
addition of concentrated sulfuric acid". The equilibrium state is reached at an
instant of time t’. Choose the correct answer. Justify.
a. t > t′ b. t = t′ c. t < t′
