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Tutorial 3

1) The document provides information on organic reactions including: ester formation from an alcohol and carboxylic acid; dehydration of an alcohol to form alkenes; and hydrolysis of an ester to reform the carboxylic acid and alcohol. 2) Multiple choice and short answer questions are provided testing the understanding of reaction types, reagents, and products. Structures and names of organic compounds are required. 3) Maximum yield calculations are presented involving a multistep reaction of cyclohexanone to the dicarboxylic acid.

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Ahmad Wahidee
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511 views8 pages

Tutorial 3

1) The document provides information on organic reactions including: ester formation from an alcohol and carboxylic acid; dehydration of an alcohol to form alkenes; and hydrolysis of an ester to reform the carboxylic acid and alcohol. 2) Multiple choice and short answer questions are provided testing the understanding of reaction types, reagents, and products. Structures and names of organic compounds are required. 3) Maximum yield calculations are presented involving a multistep reaction of cyclohexanone to the dicarboxylic acid.

Uploaded by

Ahmad Wahidee
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as DOCX, PDF, TXT or read online on Scribd
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Tutorial 3

1) Consider the compound R:

Draw the structure of the main organic product formed in each case when R reacts separately with the
following substances:
(i) methanol in the presence of a few drops of concentrated sulphuric acid;

(ii) acidified potassium dichromate(VI);

(iii) concentrated sulphuric acid in an elimination reaction.


CH3CH=CHCOOH

2) (a) Consider the following pair of isomers

(i) Name compound C.

propyl methanoate

(ii) Identify a reagent which could be used in a test-tube reaction to distinguish between
C and D. In each case, state what you would observe.
Reagent: NaHCO3

Observation with C: no reaction

Observation with D: effervescence

(b) Consider the following pair of isomers.

(i) Name compound E.

Reagent: pentan-2-one or 2-pentanone (but not pent-2-one or pentyl)

(ii) Identify a reagent which could be used in a test-tube reaction to distinguish between E and F. In each
case, state what you would observe.

Reagent: Tollens or Fehlings

Observation with E: no reaction

Observation with F: silver mirror or red ppt for E and F

3) (a) (i) Write an equation for the reaction of butan-2-ol with ethanoic acid, showing clearly the
structure of the organic product.

(ii) Name the type of organic compound formed in part (a)(i) and suggest a use for this compound.

Type of compound - ester


Use - solvent, flavourings

(iii) Give a homogeneous catalyst for the reaction in part (a)(i) and state the meaning of the term
homogeneous.
Catalyst - concentrated
H2SO4
Meaning of homogeneous - in same physical state
(b) Write an equation for the complete combustion of butan-2-ol in an excess of oxygen.
C4H10O + 6O2 4CO2 + 5H2O

4) Consider the following reaction scheme.

(a) Give the reagent(s) for Reaction 1 and name the type of reaction involved.

Reagents NaBH4
Type of reaction reduction

(b) (i) Give the reagent(s) and conditions for Reaction 2.

Reagents(s) K2Cr2O7 , H2SO4


Conditions reflux

(ii) Write an equation for this reaction using the symbol [O] to represent the oxidizing agent.
CH3CH2CH2OH + 2[O] CH3CH2COOH + H2O
(c) (i) Draw the structure and state the name of the organic product formed when Q reacts with R.

Name - propyl propanoate

(ii) Draw the structure of an isomer of R which forms ethanol on hydrolysis.

(d) Write an equation for the complete combustion of P.


CH3CH2CHO or C3H6O + 4 O2

3 CO2 + 3H2O

5) The structures of two alcohols of formula C5H11OH are shown below.

(i) A third alcohol of formula C5H11OH is tertiary. Draw the graphical formula and give the name of this
alcohol.
correct graphical formula for tertiary alcohol allow CH 3 not C2H5

2-methylbutan-2-ol / 2-hydroxy-2-methylbutane / 2-methyl-2-hydroxybutane

(ii) Draw the graphical formulae of two alkenes formed when pentan-2-ol is heated with concentrated
sulphuric acid.

(iii) State the type of reaction taking place in (a)(ii).

dehydration / elimination

(iv) Explain why the type of reaction taking place in (a)(ii) does not occur when 2,2-dimethylpropan-1-ol
is heated with concentrated sulphuric acid.

No H atoms on C atom next to COH / three methyl groups on C

6) Consider the following two reactions of cyclohexanone, C6H10O.

(a) Give a suitable reagent for Reaction 1.


NaBH4
(b) (i) Name the organic product of Reaction 3.
hexanedioic acid
(ii) Calculate the maximum mass of this organic product that could be formed if 2.40 g of cyclohexanone
were allowed to react in Reaction 3.

7) The molecular formulae of some compounds that can be prepared trom ethanoic acid are given
in the scheme below.

(a) (i) Give the name and graphical formula of P.


ethyl ethanoate

(ii) Give the name of the type of reaction which occurs when P is formed from ethanoic acid.

esterification / condensation / addition elimination

(b) Ethanoic acid can be obtained from P.


(i) Give the name of the reagent(s) and state the conditions required.

Aqueous / dilute sulphuric / hydrochloric acid (allow HCl(aq); H2SO4(aq) not water)
Temp. < 100 / warm / heat / reflux (this mark dependent on sensible reagent)

(ii) Write a balanced equation for the reaction.


CH3COOC2H5 + H2O

CH3COOH + C2H5OH

(c) State the reagent and reaction conditions that could be used for converting ethanoic acid into Q.

sodium hydroxide / sodium carbonate / sodium hydrogen carbonate (allow formula)


room temperature / aqueous (2nd mark dependent on correct reagent)

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