F.

7 Chemistry test 3
(Carboxylic acids, Nitrogen compounds)
31st Oct. 2001 Time allowed: 45 min.

1. Complete the following

a. Give the main product(s) when butanoic acid (C3H7COOH) reacts with the
following reagents:

(1) SOCl2 (2) NH3 / ∆ (3) (CH3CO)2O (4) LiAlH4 then H2O
(5) C2H5OH / H2SO4

b. CH3CH2COCl + CH3CH2COONa → ?
c. SOCl2 CH3NH2
COOH → ? → ?

? Br2 , NaOH
d. COOH → CONH2 → ?
(10m)
2. Give the product of reaction in each of the following case:
a. C2H5Br + excess NH3
b. CH2=CHCN + H2 / Pt
c. Methylmethanamine + HCl
d. C6H5NH2 + HONO → ?
e. Product from d + OH

(5m)
3. Compare the acid strength of the following compounds:

Ethanoic acid, Phenol, Benzoic acid. (2m)

4. Compare the basic strength of the following compounds:

CH3CONH2 , CH3NH2 , NH3 , NH2 (2m)

5. Predict the orders of (a) boiling points, and (b) solubilities in water, for 1o, 2o, and 3o
amines of identical molecular weights.
(3m)
6. Distinguish the following compounds by chemical method:
a. ethanol, ethanal, ethanoic acid
b.
NH2 and NHCOCH3

c. NH2 , OH , OH , NH2

(6m)
1
7. Show the steps in the following synthesis:
a. CH3CH2CHO → CH3CH2COOCH2CH2CH3
b. CH3CH2CH2CH2OH → CH3CH2CH2CH2COOH
c. CH3CH2CH2Cl → CH3CH(NH2)CH3
d. NH2 OH
→ NO2 NO
(12m)
2

8. Alanine is an amino acid with the formula CH3CHCOOH

NH2

a. What is the IUPAC name of Alanine?

b. Explain why Alanine has exceptionally high m.p.
c. Write equation to show its reaction with
(1) NaOH (2) HCl
d. Draw structure to show the dipeptide formed when two alanine molecules
combined.
(10m)
The end

2
 Suggested Answers

1. a. (1) C3H7COCl (2) C3H7CONH2 (3) --- (4) C4H9OH

(5) C3H7COOC2H5

b. (CH3CH2CO)2O

c. C6H5COCl C6H5CONH(CH3)

d. NH3 C6H5NH2

2. a. C2H5NH2

b. CH3CH2CHNH2

c. NH2(CH3)2+ Cl-

d. C6H5-N+≡N

e. N=N-C6H5
OH

3. Acid strength: Ethanoic acid > Benzoic acid > Ethanoic acid

4. Basic strength: CH3NH2 > NH3 > NH2 > CH3CONH2

5. Both boiling point and solubility are in the same order: 1o > 2o > 3o amines

6. a. Test with acid/base indicator - Ethanoic acid is acidic.

Test with 2,4-DNP (Brady’s reagent) - Ethanal shows positive result

b. Test with acid/base indicator - NH2 is basic.

Add HNO2 (0-5oC) then naphthalen-2-ol - NH2 give bright orange ppt.

c. Test with acid/base indicator

NH2 OH OH NH2

Basic Acidic Neutral More basic (effervescence occur when react

with NaNO2/HCl at temperature 0-5oC)

7. a. CH3CH2CHO K2Cr2O7/H+ CH3CH2COOH

3
 c.H2SO4

LiAlH4 H3O+ CH3CH2CH2OH

CH3CH2COOCH2CH2CH3

b. CH3CH2CH2CH2OH SOCl2 CH3CH2CH2CH2Cl KCN

CH3CH2CH2CH2CN H+ CH3CH2CH2CH2COOH

c. CH3CH2CH2Cl KOH,heat CH3CH=CH2 HBr CH3CHBrCH3

NH3 CH3CH(NH)2CH3

d. NO2 NO2 NO2

NH2 HNO2 N+≡N H2O OH

8. a. 2-Aminopropanoic acid

b. Dipolar ion structure, strong ionic attractive force between them.

c. (1) CH3CHCOO- NaOH CH3CHCOO- Na+

NH3+ NH2

(2) CH3CHCOO- HCl CH3CHCOOH

NH3+ NH3+ Cl-

d. H2N-CH-CONH-CH-COOH
CH3 CH3

The end