TOPIC: 19. Carboxylic Acids

SUBTOPIC: 200. General

5145

Six bottles, marked A, B, C, D, E, and F, contain six different pure substances: acetic acid, 2-butanone, cyclohexanol, benzamide, heptanal, and cyclohexanone, but not necessarily in that order. From the results of the six chemical tests shown below, identify the contents of each bottle.

Test No.	A	B	C	D	E	F
1	–	–	+	–	–	–
2	–	–	–	+	–	–
3	–	+	+	+	–	–
4	–	–	–	–	–	+
5	+	–	–	–	+	–
6	–	–	–	–	+	–

(+) means reaction, (-) means no reaction

Tests

1) black precipitate with Ag(NH₃)₂⁺ in water

2) yellow precipitate with NaOH/I₂/KI in water

3) yellow to orange precipitate with 2,4-dinitrophenylhydrazine solution

4) boil with dilute aqueous NaOH, vapor turns red litmus blue

5) exothermic reaction and HCl evolution when mixed with CH₃COCl

6) imparts red color to moist blue litmus

5254

State whether the following statements or equations are true or false. If any part of a statement is not true or any part of an equation is incorrect, then the item is false.

(a)

(b) the equilibrium for the reaction shown below lies to the right

pK_a 6.5 5.2

(c)

(d) relative to benzene, pyrrole is reactive toward nucleophilic sustitution, whereas pyridine is more reactive toward electrophilic substitution

pyrrole pyridine

5357

Draw the structural formulas for the major organic product(s) for five of the following reactions. Indicate clearly which five parts are to graded by circling the corresponding letters.

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

(i)

(j)