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Irina18 [472]
3 years ago
12

Draw a mechanism for this reaction. 5-hydroxypentanoic acid forms 2-oxanone in the presence of acid. draw all missing reactants

and/or products in the appropriate boxes by placing atoms on the canvas and connecting them with bonds. add charges where needed. electron flow arrows should start on an atom or a bond and should end on an atom, bond, or location where a new bond should be created.
Chemistry
1 answer:
Licemer1 [7]3 years ago
3 0

Answer: -

The first step involves protonation of the carbonyl oxygen.

After protonation, the Alcohol oxygen now attacks the carbon of the carbonyl.

Thus a six membered ring is formed with 5 carbon atoms and 1 oxygen atom. The 1st position carbon atom has 2 OH groups.

One of these gets again protonated.

This leaves as water. With the loss of the H+, there results a carbonyl at 1 position.

Thus 5-hydroxypentanoic acid forms a lactone or 2-oxanone in presence of acid.

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Consider the titration of 100.0 mL of 0.280 M propanoic acid (Ka = 1.3 ✕ 10−5) with 0.140 M NaOH. Calculate the pH of the result
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Answer:

(a) 2.7

(b) 4.44

(c) 4.886

(d) 5.363

(e) 5.570

(f)  12.30

Explanation:

Here we have the titration of a weak acid with the strong base NaOH. So in part (a) simply calculate the pH of a weak acid ; in the other parts we have to consider that a buffer solution will be present after some of the weak acid reacts completely the strong base producing the conjugate base. We may even arrive to the situation in which all of the acid will be just consumed and have only  the weak base present in the solution treating it as the pOH and the pH = 14 -pOH. There is also the possibility that all of the weak base will be consumed and then the NaOH will drive the pH.

Lets call HA propanoic acid and A⁻ its conjugate base,

(a) pH = -log √ (HA) Ka =-log √(0.28 x 1.3 x 10⁻⁵) = 2.7

(b) moles reacted HA = 50 x 10⁻³ L x 0.14 mol/L = 0.007 mol

mol left HA = 0.28 - 0.007 = 0.021

mol A⁻ produced = 0.007

Using the Hasselbalch-Henderson equation for buffer solutions:

pH = pKa + log ((A⁻/)/(HA)) = -log (1.3 x 10⁻⁵) + log (0.007/0.021)= 4.89 + (-0.48) = 4.44

(c) = mol HA reacted = 0.100 L x 0.14 mol/L = 0.014 mol

mol HA left = 0.028 -0.014 = 0.014 mol

mol A⁻ produced = 0.014

pH = -log (1.3 x 10⁻⁵) + log (0.014/0.014) =  4.886

(d) mol HA reacted = 150 x 10⁻³ L  x  x 0.14 mol/L = 0.021 mol

mol HA left = 0.028 - 0.021 = 0.007

mol A⁻ produced = 0.021

pH = -log (1.3 x 10⁻⁵) + log (0.021/0.007) =  5.363

(e) mol HA reacted = 200 x 10⁻³ L x 0.14 mol/L = 0.028 mol

mol HA left = 0

Now we only a weak base present and its pH is given by:

pH  = √(kb x (A⁻)  where Kb= Kw/Ka

Notice that here we will have to calculate the concentration of A⁻ because we have dilution effects the moment we added to the 100 mL of HA,  200 mL of NaOH 0.14 M. (we did not need to concern ourselves before with this since the volumes cancelled each other in the previous formulas)

mol A⁻ = 0.028 mOl

Vol solution = 100 mL + 200 mL = 300 mL

(A⁻) = 0.028 mol /0.3 L = 0.0093 M

and we also need to calculate the Kb for the weak base:

Kw = 10⁻¹⁴ = ka Kb ⇒   Kb = 10⁻¹⁴/1.3x 10⁻⁵ = 7.7 x 10⁻ ¹⁰

pH = -log (√( 7.7 x 10⁻ ¹⁰ x 0.0093) = 5.570

(f) Treat this part as a calculation of the pH of a strong base

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mol OH remaining = 0.035 mol - 0.028 reacted with HA

= 0.007 mol

(OH⁻) = 0.007 mol / 0.350 L = 2.00 x 10 ⁻²

pOH = - log (2.00 x 10⁻²) = 1.70

pH = 14 - 1.70 = 12.30

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Explanation:

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