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(a)
O C O OH O C C H
ASA (b)
H H
H H H N C N H
urea
N C
C N
O O
CH3
theobromine
CH3
caffeine
Figure 1 (a) More than ten million kilograms of Aspirin, or acetylsalicylic acid (ASA), are produced in North America annually. Because of this compounds ability to reduce pain and inflammation, it is the most widely used medicine in our society. (b) Urea, the organic compound first synthesized by Whler in 1828, is produced in even larger quantities than ASA. Urea is used primarily as plant fertilizer and as an animal feed additive.
Throughout our study of organic families, we have focused on the transformation of functional groups. Let us take our knowledge of these reactions and devise a method of preparing a more complex molecule from simpler ones. Lets say that we have been assigned the task of preparing an ester with a pineapple flavour, to be used in candies. We have available a number of short-chain alkanes and alkenes as starting materials. What substance will we make, which starting materials should we use, and what steps should we take in the synthesis?
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Chapter 1
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Section 1.9
O CH3CH2CH2C O CH2CH3
ethyl butanoate
Let us apply the backwards approach to the synthesis of ethyl butanoate, the ester with a pineapple flavour. As the name and structure show, this ester is formed from a reaction between ethanol and butanoic acid. The steps in our multi-step procedure are shown in the sample problem below. Of course, there is more than one possible synthesis pathway for any product; when selecting a procedure, industrial chemists always pay attention to the availability and cost of starting materials, as well as safety and environmental concerns.
SAMPLE problem
CH3CHCH2CH3 OH
CH2CH
CHCH3
H 2O
H2SO4
CH3CHCH2CH3 OH
Other reagents and reactions are available for preparing primary alcohols, as you may learn in future chemistry courses. For this synthesis, we will use 1-butanol as our starting material to prepare butanoic acid. Our pathway is now complete.
ethanol (alcohol)
1-butanol (alcohol)
NEL
Organic Compounds
81
Example
Write a series of equations for the synthesis of propanone, starting with an alkene.
Solution
1. CH3CH
CH2
H2O
CH3CH(OH)CH3
ACTIVITY 1.9.1
Building Molecular Models to Illustrate Reactions (p. 90) What do molecules really look like, and how does one substance turn into another? This activity helps you visualize, using molecular models, how reactions happen.
2.
propene
2-propanol
O
CH3CH(OH)CH3
2-propanol
(O)
CH3CCH3
propanone
Practice
Understanding Concepts
1. A food additive that is named as a single ingredient is often a mixture of many
ACTIVITY 1.9.2
Preparation of an Ester Aspirin (p. 90) The reaction between salicylic acid and acetic anhydride produces a well-known pharmaceutical product.
compounds. For example, a typical artificial strawberry flavour found in a milkshake may contain up to 50 different compounds. A few of these are listed below. For each, write a structural formula and an equation or a series of equations for a method of synthesis from the suggested reactants. (a) 2-pentyl butanoate from pentene and butanal (b) phenyl 2-methylpropanoate from phenol and an appropriate alcohol (c) 4-heptanone from an alcohol (d) ethyl ethanoate from ethene
tion or a series of equations for a method of synthesis from other compounds. (a) pentyl ethanoate from ethene and an alcohol (b) phenyl ethanoate from an alkene and an alcohol (c) 3-octanone from a simpler compound (d) methyl benzoate from two alcohols (e) sodium salt of butanoic acid from an ester (f) trimethylamine from ammonia and alkanes (g) N-ethylethanamide from an alkane and ammonia
2. The smell of freshly cut grass can be simulated by the addi-
2-methylbutanoate. (a) Draw a flow chart to show the synthesis of this compound, starting with simpler compounds. (b) Describe the steps in the procedure for this synthesis. Include experimental conditions and safety precautions in the handling and disposal of materials. Making Connections
4. The flavour of almonds is obtained from phenyl methanal,
tion of hexanal to substances such as air-fresheners. Describe how hexanal can be made from an alcohol.
also called benzaldehyde. Natural almond flavour is extracted from the pit of peaches and apricots, and may contains traces of the poison hydrogen cyanide. (a) Write a structural diagram for benzaldehyde. (b) Write equations for a series of reactions in the synthesis of benzaldehyde from an ester.
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Section 1.9
(c) Research and describe the toxicity of the reactants listed in (b), and compare the toxicity to that of hydrogen cyanide. In your opinion, do your findings substantiate consumer perception that natural products are always healthier than their artificial counterparts?
in organic products, why might there be some confusion about what the new job involves?
7. Look at the product labels on foods, pharmaceuticals, and
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tropical disease that kills or incapacitates millions of people every year. Quinine has a bitter taste and was mixed with lemon or lime to make it palatable; it was later included as a component of a beverage called tonic water. (a) Tonic water contains approximately 20 mg quinine per 375-mL can; the dosage required for the treatment of malaria is approximately six 300-mg tablets per day. In your opinion, would drinking tonic water be an effective approach to the treatment of malaria? Explain. (b) Refer to the structural diagram of quinine (Figure 2), and explain why quinine is soluble in water. (c) Research the effectiveness of quinine as an antimalarial agent from the early 1800s to the present.
dietary supplements in a supermarket or drugstore. In particular, look for the terms organic, natural, and chemical. What is the purpose of using these terms on the packaging? Do they always mean the same thing? Do they have a positive or negative connotation? Write a short opinion piece on the use of these three terms, and what these terms mean to consumers.
CH=CH2 N H CH2OH N
Figure 2 Structure of quinine
HO
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SUMMARY
+ H2
substitution alkanes
+ HX
alkyl halides
+ H2O + H2O
1 alcohol (O)* aldehydes alcohols 2 alcohol (O)* ketones dehydration
+ X2
+ NH3
amines *(O) indicates controlled oxidation with KMnO4 or Cr2O72, in H2SO4 amine
(H2SO4)
ethers
(O)*
carboxylic acids alcohol condensation amides esters
NEL
Organic Compounds
83