Student Copy Carboxylic Acid Derivatives

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 1/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 2/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 3/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 4/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 5/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 6/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 7/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 8/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 9/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 10/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 11/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 12/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 13/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 14/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 15/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 16/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 17/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 18/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 19/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 20/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 21/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 22/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 23/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 24/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 25/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 26/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 27/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 28/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 29/36

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 30/36

(c) CompoundF and G are isomers ofE .

(i) Suggest the order of acid strength ofE

,F

andG

.(ii) Based on their relative acidities, suggest how samples ofE ,

F and G could be distinguished from each other by use of

NaOH (aq) and Na2CO3 (aq). 3 [A2 Nov 2003 Paper IV Q4]

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 31/36

Solution

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 32/36

Q: 4

Chloroacetophenone (compoundD below) is formerly the mostwidely used tear gas, under the codenameCN . It is used in

warfare and in riot control. It can be synthesized from

ethylbenzene, A, by the following route.

(a) Suggest reagents and conditions for stepI. 1

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 33/36

(b) Suggest reagents and conditions for converting ethylbenzene

into compoundE , an isomer ofB . 1

(c) Draw the structure of the product obtained by heating

ethylbenzene with KMnO4. 1

(d) Describe a test (reagents and observations) that woulddistinguish compoundC from compoundF . 2

ReagentsObservation withC

Observation withF

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 34/36

(f) Residues ofCN can be destroyed by hydrolysis with anaqueous alkali.

CompoundsG and H are isomers of compoundD.

(i) Arrange the three isomersD, G and H in order of increasing

ease of hydrolysis.(ii) Explain the reasoning behind your choice. 3

[A2 June 2003 Paper IV Q4]

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 35/36

Solution

8/12/2019 Student Copy Carboxylic Acid Derivatives

http://slidepdf.com/reader/full/student-copy-carboxylic-acid-derivatives 36/36

Q: 5

[A2 June 2013 Paper 41 Q5](a) A series of experiments is carried out in which the reagent

shown at the top of the column of the table is mixed, in turn,

with each of the reagents at the side.Complete the following table by writing in each box the formul

of any gas produced. Writex in the box if no gas is produced.

The first column has been completed as an illustration.