CHAPTER 7: Organic Functional Groups
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1 CHAPTER 7: Organic Functional Groups PRACTICE PROBLEM Epinephrine (adrenaline) is a hormone secreted when the body is under stress. Illicit drugs that are structurally similar to epinephrine are highly addictive stimulants. For example, the illegal and addictive drug methamphetamine is similar in structure to epinephrine. However, pseudoephedrine, which is structurally similar to epinephrine, is a decongestant and sold over the counter in pharmacies. a. Circle and label all the amine functional groups in these molecules. b. In what way is methamphetamine structurally similar to pseudoephedrine? How is it different? c. In the body, the amine in epinephrine is in its ionic form. Write the structure of the ionic form of epinephrine.
2 CHAPTER 7: Organic Functional Groups PRACTICE PROBLEM Epinephrine (adrenaline) is a hormone secreted when the body is under stress. Illicit drugs that are structurally similar to epinephrine are highly addictive stimulants. For example, the illegal and addictive drug methamphetamine is similar in structure to epinephrine. However, pseudoephedrine, which is structurally similar to epinephrine, is a decongestant and sold over the counter in pharmacies. a. Circle and label all the amine functional groups in these molecules. b. In what way is methamphetamine structurally similar to pseudoephedrine? How is it different? c. In the body, the amine in epinephrine is in its ionic form. Write the structure of the ionic form of epinephrine.
3 Saponification Reaction converting fats to soap with glycerol as a byproduct Involves base hydrolysis Reaction with NaOH
4 Saponification (CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 COOCH 2) 3 CH CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CO O - Na + C 3 H 8 O 3 (CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 COOCH 2) 3 CH + 3 NaOH 3 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CO + C 3 H 8 O 3 O - Na +
5 Saponification (CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 COO CH 2 ) 3 CH + 3 NaOH 3 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CO + C 3 H 8 O 3 O - Na + MW = MW = 40 MW = MW = ) What is the theoretical yield for the soap product if 5g of triglyceride react? OR (same question) CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 How many grams of COO - Na + are produced by reacting (CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 COO CH 2 ) 3 CH 5.0 grams of with excess NaOH? 2) If 4.0 grams of CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 are recovered after the reaction, COO - Na + then what is the percent yield?
6 Saponification (CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 COO CH 2 ) 3 CH + 3 NaOH 3 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CO + C 3 H 8 O 3 O - Na + MW = MW = 40 MW = MW = ) What is the theoretical yield for the soap product if 5g of triglyceride react? OR (same question) CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 How many grams of COO - Na + are produced by reacting (CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 COO CH 2 ) 3 CH 5.0 grams of with excess NaOH? 2) If 4.0 grams of CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 are recovered after the reaction, COO - Na + then what is the percent yield?
7 Saponification (CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 COOCH 2) 3 CH + 3 NaOH 3 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CO + C 3 H 8 O 3 O - Na + MW = MW = 40 MW = MW = How many grams of CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 COO - Na grams of with excess NaOH? (CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 COOCH 2) 3 CH Answer: 5.9 grams are expected to be produced by reacting If 4 grams of CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 COO - Na + are recovered after the reaction, then what is the percent yield? Answer: 67.8 %
8 Saponification (CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 COO CH 2 ) 3 CH + 3 NaOH 3 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CO + C 3 H 8 O 3 O - Na + MW = MW = 40 MW = MW = ) What is the theoretical yield for the glycerol if 5g of triglyceride react? OR (same question) How many grams of glycerol are produced by reacting (CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 COO 5.0 grams of CH 2 ) 3 CH with excess NaOH? 4) If 0.8 g of glycerol is recovered after the reaction, then what is the percent yield for glycerol?
9 Saponification (CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 COO CH 2 ) 3 CH + 3 NaOH 3 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CO + C 3 H 8 O 3 O - Na + MW = MW = 40 MW = MW = ) What is the theoretical yield for the glycerol if 5g of triglyceride react? OR (same question) How many grams of glycerol are produced by reacting (CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 COO 5.0 grams of CH 2 ) 3 CH with excess NaOH? 4) If 0.8 g of glycerol is recovered after the reaction, then what is the percent yield for glycerol?
10 ph Practice Problems Find the ph of a ml solution containing g of Calcium Hydroxide.
11 Hints 1. First, find the molarity of the solution. 2. Ask yourself the following: a. Is Calcium Hydroxide acidic or basic? b. Is it strong or weak? 3. Write the reaction. 4. Find the ph.
12 Working Out the Problem
13 1. Finding the Molarity Given: g Calcium Hydroxide ml = L solution a. What is the equation for molarity? molesof solute Molarity= volume of solution( L) b. Find the moles of Calcium Hydroxide. Molar Mass = (40.08 g Ca) + (16 g x 2 O) + (1.01 g x 2 H) Molar Mass = 74.1 g g Ca(OH)2 x 1 mol Ca(OH) g Ca(OH) mol c. Find the molarity. Molarity= mol L = M
14 2. Think about Calcium Hydroxide Is Calcium Hydroxide acidic or basic? Calcium Hydroxide is basic. Is it strong or weak? It is a strong base.
15 3. Write the reaction. Ca(OH) 2 Ca OH Calcium Hydroxide is a strong base. This means it dissociates completely into calcium and hydroxide ions.
16 4. Find the ph a. What are the relevant ph equations? ph = log([h+]) poh = log([oh ]) ph + poh = 14 b. Ca(OH) 2 Ca OH poh = log ( M x 2 OH ) poh = ph = 14 poh ph = Does this answer make sense? Why or why not? Note: Because M Ca(OH) 2 is a strong base, we assume it dissociates completely. This means the concentration of Calcium ions is M. Looking at the reaction, we can see that the concentration of Hydroxide ions is twice that of Calcium (Ca OH ). That is why we multiply the concentration by 2.
17 Acids and Bases A buffer solution is an aqueous solution consisting of a mixture of A weak acid and its conjugate base A weak base and its conjugate acid Buffers help keep a solution close to a specific ph H 2 PO 4 - (aq) H + (aq) + HPO 4 2- (aq) Weak Acid Conjugate Base
18 Acids and Bases H 2 PO - 4 (aq) H + (aq) + HPO 2-4 (aq) ΔH = kj/mol In which direction will the reaction shift if 1. If H 2 PO 4- is added? 2. If acid is added? 3. If the solution is heated?
19 Acids and Bases H 2 PO - 4 (aq) H + (aq) + HPO 2-4 (aq) ΔH = kj/mol In which direction will the reaction shift if 1. If H 2 PO 4- is added? Right 1. If acid is added? Left 2. If the solution is heated?right
20 Buffers in blood The carbonic acid/ bicarbonate ion buffer system is present in our blood. It is responsible for maintaining blood ph within Acidosis- blood ph drops below normal range Alkalosis- blood ph is higher than normal range
21 Buffers in blood H 2 CO 3 + H 2 O HCO 3- + H 3 O + Which of these acts as a base? Which acts as an acid? Considering Le Châtelier s Principle If there is an excess of CO 2 dissolved in the blood forming carbonic acid, in which direction would this reaction proceed?
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