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Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids

Chapter Fourteen

Carboxylic Acids

Problem 14.1: Suggest the IUPAC name for each of the following compounds.

Solution

(a) 2-Cyclohexenecarboxylic acid (b) 2-Cyclopropylpropanoic acid (c) 1,5-Pentanedioic acid (d) 4-Oxo-pent-2-enoic acid (e) Benzene-1,3-dicarboxylic acid Problem 14.2: Predict the major product for the following reactions. Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids

Solution:

Problem 14.3: How could you separate a mixture containing the following compounds?

C6H5CO2H , C6H5OH , C6H5CONHC6H5

Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids

Solution

Problem 14.4: Rank in the order of decreasing acidity. (a) 1 > 2 > 3 > 4 (b) 1 > 3 > 2 > 4 (c) 1 > 4 > 2 > 3 (d) 2 > 1 > 3 > 4 (d) 2 > 3 > 1 > 4 (e) 2 > 4 > 1 > 2 Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids (f) 2 > 4 > 3 > 1 (g) 3 > 4 > 2 > 1

Solution: (f)

Problem 14.5: Give the formula for compounds A to F.

Solution

A = RCOCl B = RCON(CH3)2

C = RCH2N(CH3)2 D = RCH2N+(CH3)2I

E = Problem 14.6: Select the correct answer of the following:

1- The reaction of formic acid with conc. H2SO4 gives.

(a) CO2+H2O (b) HCHO (c) CH3CO2H (d) CO+H2O

2- Propanoic acid when treated with aq. NaHCO3, the

CO2 comes from.

(a) CH3 (b) Methylene (c) Bicarbonate (d) Carboxylic acid

3- The acid, which has reducing properties, is.

Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids (a) Formic acid (b) Acetic acid (c) Oxalic acid (d) Ethanoic acid

4- Carboxylic acid when warmed with hydrazoic acid

(HN3) in the presence of H2SO4, its produces. (a) Acid amide (b) Primary amine (c) Alkyl cyanide (d) Secondary amine

5- Which one is the strongest acid?

(a) -Nitrobenzoic acid (b) -Nitrobenzoic acid (c) -Nitrobenzoic acid (d) -Nitrophenol

Solution

1- (d) 2- (c) 3- (a) 4- (b) 5- (a)

Problem 14.7: Select the correct answer of the following:

1- Formic acid and acetic acid may be distinguished by

reaction with (a) Na (b) C2H5ONa (c) dil. KMnO4 (d) 2,4-(NO2)2 C6H3NHNH2

2- Benzoic acid and phenol may be distinguished by their

reaction with (a) aq. NaOH (b) aq. NaHCO3 Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids (c) FeCl3 (d) aq. NH3

3- The IUPAC name of CH3CH2CH=CHCO2H is

(a) Pent-3-en-1-oic acid (b) Pent-2-en-1-oic acid (c) Pent-2,3-en-1-oic acid (d) Pent-3,4-en-1-oic acid

4- Benzoic acid reacts with conc. HNO3 and conc. H2SO4

to give. (a) -Nitrobenzoic acid (b) -Nitrobenzoic acid (c) -Nitrobenzoic acid (d) -and -Nitrobenzoic acid

5- -Methoxybenzoic acid is less acidic than salicylic

acid because of the: (a) Resonance (b) Inductive effect (c) Hydrogen bond (d) None of these

6- Pyruvic acid can be obtained by the oxidation of

propanic acid with. (a) KMnO4 (b) Ag2O (c) MnO2 (d) SeO2

7- The final product for the acid hydrolysis and the

decarboxylation of Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids

Solution

1- (c) 2- (b, c) 3- (b) 4- (b)

5- (c) 6- (d) 7- (c)

Problem 14.8: Give the name for each of the following compounds.

1- HCO2H 2- CH3CO2H

3- CH3CH2CO2H 4- CH3CH2CH2CO2H

5- CH3CH2CH2CH2CO2H 6- (CH3)3CCO2H

7- C6H5CH2CO2H

Solution

Common system Derived system IUPAC system

1- Formic acid --- Methanoic acid

2- Acetic acid --- Ethanoic acid

3- Propionic acid Methyl acetic acid Propanoic acid

4- Butyric acid Ethyl acetic acid Butanoic acid

5- Valeric acid Propyl acetic acid Pentanoic acid

6- --- Trimethyl acetic acid 2,3-Dimethylpropanoic acid

7- --- Phenyl acetic acid 2-Phenylethanoic acid

Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids Problem 14.9: Predict the products of the following.

Solution:

1- CH3COONa + H2O + CO2

2- CH3COCl + POCl3 + HCl

3- CH3CONH2 + H2O

4- ClCH2COOH + HCl

Problem 14.10: How will you distinguish between

1- Crotonic acid and propionic acid?

2- Formic acid and acetic acid?

Solution

1- Crotonic acid is an unsaturated acid, it decolorizes the

red color of Br2 / CCl4 solution, but propionic acid does not give this test. Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids

2- A-By Tollen's reagent: Formic acid produces silver

mirror with ammonical silver nitrate solution, but acetic acid does not give this test. B- By mercuric chloride : Formic acid produces a white precipitate with HgCl2 solution but acetic acid does not give this test. Problem 14.11: How will you convert acetic acid to: (1) Sodium acetate? (2) Acetyl chloride? (3) Acetamide? (4) Acetic anhydride? (5) Ethanol? (6) Chloroacetic acid?

Solution:

Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids Problem 14.12 Arrange the following compounds in the order of increasing acidity.

1- ClCH2CO2H, Cl2CHCO2H, Cl3CCO2H, CH3CO2H

2- CH3CO2H, (CH3)2CHCO2H, (CH3)3CCO2H

Solution:

1- CH3CO2H < ClCH2CO2H < Cl2CHCO2H < Cl3CCO2H

2- (CH3)3CCO2H < (CH3)2CHCO2H < CH3CO2H

Problem 14.13: Identify A, B and C in the following reaction sequences. Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids

Solution:

1 A: CH3CH2Br B : CH3CH2CN C: CH3CH2CO2H

2 A: (CH3CO)2Cu B : CH3COCH3 C:(CH3)2C=NNH2

3 A:CH3CH(OH)CN B: CH3CH(OH)CO2H C: CH3COCO2H

4 A: CH3CH2Br B : CH3CH2CN C: CH3CH2CO2H

Problem 14.14 How will you synthesize:

(1) Acetic acid from acetylene? (2) Acetic acid from propionic acid? (3) Propionic acid from acetic acid ?

Solution:

Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids

Problem 14.15 How will you synthesize.

(1) Isobutyric acid from isopropyl alcohol? (2) Chloroacetic acid from methyl chloride? (3) Pyruvic acid from ethyl bromide? (4) Glycine from ethyl alcohol? (5) Malonic acid from acetic acid?

Solution

Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids Problem 14.16 How will you synthesize crotonic acid from acetaldehyde? Solution Crotonic acid could be synthesized from acetaldehyde using two methods . (1) Via aldol condensation. (2) Via Knoevenagel condensation.

Problem 14.17How will you synthesize.

(1) Trimethyl acetic acid from -butylalcohol? (2) 2,4,6-Trimethylbenzoic acid from 2,4,6-trimethylbenzene?

Solution

Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids

Problem 14.18 A fatty acid contains the group of.

(a) ±OH (b) C=O (c) ±CONH2 (d) ±CO2H

Solution: (d)

Problem 14.19 Select the correct answers:

1- A carboxylic acid contains of

(a) HO- (b) C=O (c) HO- & C=O (d) CONH2

2- Methanoic acid bears functional groups of :

(a) CO2H (b) HO- (c) C=O & OH (d) CO2H & OH and CHO Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids

3- Methanoic acid differs from ethanoic acid in the

reaction with. (a) FeCl3 (b) NaHCO3 (c) KMnO4 (d) C2H5OH

4- The reaction between a carboxylic acid and alcohol is

known as (a) Condensation (b) Hydrolysis (c) Esterification (d) Carbonation

5- Mark the acid which is by decarboxylation does not

give a hydrocarbon. (a) Formic acid (b) Acetic acid (c) Benzoic acid (d) Propionic acid

6- Which of the following acids cannot be prepared by

reaction of Grignard's reagent and CO2? (a) Acetic acid (b) Formic acid (c) Propionic acid (d) Benzoic acid

7- Ammonium acetate by heating with P2O5 gives.

(a) Acetic anhydride (b) Acetamide (c) Acetonitrile (d) Ethylamine

8- Acetic acid can be manufactured by.

(a) Fermentation (b) Distillation (c) Saccharification (d) Ozonolysis Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids

Solution:

1- c 2- d 3- c 4- c

5- a 6- b 7- c 8- a

Problem 14.20: Chose the correct answers:

1- The acid that present in the vinegar is.

(a) Citric acid (b) Acetic acid (c) Formic acid (d) Oxalic acid

2- Mark the acid that reduces Tollen's reagent.

(a) Acetic acid (b) Formic acid (c) Propionic acid (d) Carbonic acid

3- Formic acid on heating yields.

(a) CO2 + H2O (b) CO + H2O (c) CO + H2 (d) None of these

4- The acid used in pickling is:

(a) Formic acid (b) Acetic acid (c) Citric acid (d) Tartaric acid

5- When methyl alcohol vapour, mixed with carbon

monoxide, and passed under pressure at 150C° over a catalyst, the product was. (a) Formic acid (b) Acetic acid Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids (c) Propionic acid (d) Oxalic acid

6- Mark the strongest acid:

(a) HCO2H (b) CH3CO2H (c) ClCH2CO2H (d) Cl3CCO2H

7- Which acids is used in the manufacture of synthetic

fibers? (a) Formic acid (b) Acetic acid (c) Carbonic acid (d) Oxalic acid

8- When hydrogen ion is removed from the carboxylic

acid, the fragment left is. (a) An acyl group (b) An acetyl group (c) An acyloxy group (d) None of these

Solution

1- b 2- b 3- d 4- b

5- b 6- d 7- b 8- c

Problem 14.21Give the name of the following compounds. Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids

Solution

a- (E)-2-Methyl-2-butenoic acid (tiglic acid) b- (Z)-2-Methyl-2-butenoic acid (angelic acid) c- 2-Hydroxypropane-1,2,3-tricarboxylic acid (citric acid) d- 3,5-Dihydroxy-3-methylpentanoic acid (mevalonic acid) Problem 14.22: How will you convert the following reaction?

Solution:

Chapter Fourteen Fawzi Hameeed Jumaa Al-Obaidy Carboxylic Acids Problem 14.23 Provide an acceptable IUPAC name for each of the following:

Solution

(a) 4-Methyl-5-phenylhexanoic acid (b) Cyclohexanecarboxylic acid (c) 3-Methyl-2-ethylbutanoic acidquotesdbs_dbs4.pdfusesText_7

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