[Maximum number: 1]

Propanoic acid is treated with reagent X at room temperature. The organic product of the reaction is sodium propanoate. No gas is produced during the reaction.

What could be reagent X ?

A

$\mathrm{NaHCO}_{3}(\mathrm{aq})$

B

NaOH(aq)

C

$\mathrm{Na}_{2} \mathrm{CO}_{3}(\mathrm{aq})$

D

$\mathrm{Na}_{2} \mathrm{SO}_{4}(\mathrm{aq})$

[Maximum number: 2]

Iron is a transition element in the fourth period. Iron forms compounds containing the ions $\mathrm{Fe}^{2+}$ and $\mathrm{Fe}^{3+}$ .

(a)

E is a complex ion, $\left[\mathrm{Fe}\left(\mathrm{C}_{2} \mathrm{O}_{4}\right)_{2} \mathrm{C} l_{2}\right]^{4-}$ , containing $\mathrm{Fe}^{2+}$ with a coordination number of 6 .

[ 2 ]

(i)

$\left[\mathrm{Fe}\left(\mathrm{C}_{2} \mathrm{O}_{4}\right)_{2} \mathrm{Cl}_{2}\right]^{4-}$ contains ligands which are anions of ethanedioic acid, $\mathrm{HO}_{2} \mathrm{CCO}_{2} \mathrm{H}$ .

Complete the table to show any observations for the reactions of $\mathrm{HO}_{2} \mathrm{CCO}_{2} \mathrm{H}$ with the named reagents.

Where no change is observed, write 'none'.

[ 2 ]

[Maximum number: 3]

Barium hydroxide, $\mathrm{Ba}(\mathrm{OH})_{2}$ , is a strong base used in inorganic and organic reactions.

$Fig. 2.1 shows a reaction scheme involving \(\mathrm{Ba$

Fig. 2.1 shows a reaction scheme involving \(\mathrm{Ba

(a)

$\mathrm{Ba}(\mathrm{OH})_{2}$ is used to hydrolyse organic compounds.

Fig. 2.2 shows the reaction of B with $\mathrm{Ba}(\mathrm{OH})_{2}$ , followed by acidification.
Draw the structures of the organic products of the process shown in Fig. 2.2.

Fig. 2.2

[ 3 ]

[Maximum number: 1]

Which substance, when warmed with aqueous ammonium chloride, would produce an alkaline gas?

A

$\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}$

B

$\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}$

C

$\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{CH}_{3}$

D

$\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{ONa}$

(a)

Propanoic acid, $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}$ , is a weak acid with $K_{\mathrm{a}}=1.34 \times 10^{-5} \mathrm{~mol} \mathrm{dm}^{-3}$ .

[ 6 ]

(i)

Write an equation for the reaction between sodium hydroxide and propanoic acid.

[ 6 ]

[Maximum number: 7]

Compound R is a weak diprotic (dibasic) acid which is very soluble in water.

(a)

State the reagent(s) and essential conditions that would be used for the following conversions.

S into T
S into U

T into S

[ 5 ]

(b)

Give the structural formula of the organic product formed in each of the following reactions.

T reacting with an excess of Na

U reacting with an excess of $\mathrm{Na}_{2} \mathrm{CO}_{3}$

[ 2 ]

[Maximum number: 1]

A compound Y has all of the properties below.
- It is a liquid at $25^{\circ} \mathrm{C}$ .
- It mixes completely with water.
- It reacts with aqueous sodium hydroxide.

What could Y be?

A

ethanoic acid

B

ethanol

C

ethene

D

ethyl ethanoate

[Maximum number: 1]

An organic compound J reacts with sodium to produce an organic ion with a charge of -3 . J reacts with NaOH(aq) to produce an organic ion with a charge of -1 .

What could be the structural formula of J ?

A

$\mathrm{HO}_{2} \mathrm{CCH}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}$

B

$\mathrm{HO}_{2} \mathrm{CCH}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{CHO}$

C

$\mathrm{HOCH}_{2} \mathrm{CH}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}$

D

$\mathrm{HOCH}_{2} \mathrm{COCH}_{2} \mathrm{CHO}$

[Maximum number: 1]

Butanedioic acid may be synthesised in two steps from 1,2-dibromoethane.

\mathrm{BrCH}_{2} \mathrm{CH}_{2} \mathrm{Br} \xrightarrow{\text { step 1 }} \mathrm{X} \xrightarrow{\text { step 2 }} \mathrm{HO}_{2} \mathrm{CCH}_{2} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}

Which reagents could be used for this synthesis?

step 1

step 2

HCN(g)

HCl(aq)

$\mathrm{HCO}_{2} \mathrm{Na}(\mathrm{aq})$

HCl(aq)

KCN( alcoholic )

$\mathrm{H}_{2} \mathrm{SO}_{4}(\mathrm{aq})$

NaOH(aq)

$\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7} / \mathrm{H}_{2} \mathrm{SO}_{4}(\mathrm{aq})$

[Maximum number: 1]

In a sequence of reactions, ethanal is converted into a compound H.

What could H be?

A

$\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOCH}_{3}$

B

$\mathrm{CH}_{3} \mathrm{CH}(\mathrm{OH}) \mathrm{COOCH}_{3}$

C

$\mathrm{CH}_{3} \mathrm{CH}(\mathrm{OH}) \mathrm{OCOCH}_{3}$

D

$\mathrm{CH}_{3} \mathrm{CH}\left(\mathrm{OCH}_{3}\right) \mathrm{COOH}$