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- Herausgeber: John Wiley & Sons
- Kategorie: Wissenschaft und neue Technologien
- Sprache: Englisch
This book opens the audience's eyes to the extraordinary scientific secrets hiding in everyday objects. Helping readers increase chemistry knowledge in a fun and entertaining way, the book is perfect as a supplementary textbook or gift to curious professionals and novices. * Appeals to a modern audience of science lovers by discussing multiple examples of chemistry in everyday life * Addresses compounds that affect everyone in one way or another: poisons, pharmaceuticals, foods, and illicit drugs; thereby evoking a powerful emotional response which increases interest in the topic at hand * Focuses on edgy types of stories that chemists generally tend to avoid so as not to paint chemistry in a bad light; however, these are the stories that people find interesting * Provides detailed and sophisticated stories that increase the reader's fundamental scientific knowledge * Discusses complex topics in an engaging and accessible manner, providing the "how" and "why" that takes readers deeper into the stories
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Seitenzahl: 573
Veröffentlichungsjahr: 2017
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Table of Contents
Cover
Title Page
Copyright
Dedication
Preface
Acknowledgments
Chapter 1: If You Do Not Know Any Chemistry, This Chapter Is For You
Representing Atoms and Molecules in Chemistry
Neurotransmitters
Intermolecular Forces
Chapter 2: The Only True Aphrodisiac and Other Chemical Extremes
Death Is Its Withdrawal Symptom!
What Is the Number One Cause of Liver Failure in the United States?
The Most Addictive Substance Known
40 Million Times Deadlier Than Cyanide
The Most Abused Drug in the United States
What Is the Only Known Aphrodisiac?
The Most Consumed Psychoactive Substance
40,000 Tons of Aspirin
How Bitter Is the Bitterest?
$62.5 Trillion per Gram
What Is the Most Abundant Source of Air Pollution?
Where Did That Rash Come From?
It Would Take an Elephant on a Pencil
The Largest Industrial Accident in World History
What Is the Most Important Chemical Reaction?
Further Reading
Death is its Withdrawal Symptom!
What is the Number One Cause of Liver Failure in the United States?
The Most Addictive Substance Known
40 Million Times Deadlier Than Cyanide
The Most Abused Drug in the United States
The Only Known Aphrodisiac
The Most Consumed Psychoactive Substance
40,000 Tons of Aspirin
How Bitter is the Bitterest?
$62.5 Trillion per Gram
What is the Most Abundant Source of Air Pollution?
Where Did That Rash Come From?
It Would Take an Elephant on a Pencil
The Largest Industrial Accident in World History
What is the Most Important Chemical Reaction?
Chapter 3: The Poisons in Everyday Things
Why Is Antifreeze Lethal?
Aqua Dots: What a Difference a Carbon Makes!
How Can Visine® Kill You?
Death by BENGAY®
It Is in 93 of People in the United States
The Dreaded…Apricot Pits?
Honey Intoxication
The DMSO Patient
Deadly Helium Balloons
The 2007 Pet Food Recall
Mercury in Vaccines and Eye Drops?
The World's Deadliest Frog
Leaded Candy
Why not Drink “Real” Root Beer?
The Killer Fog
Nail Polish or Nail Poison?
Game Board Danger
What Molecule Killed “Weird Al” Yankovic's Parents?
Deadly Popcorn
Even Water Can Be Poisonous
Further Reading
Why is Antifreeze Lethal?
Aquadots: What a Difference a Carbon Makes!
How can Visine® Kill You?
Death by BENGAY®
It Is in 93% of People in the United States
The Dreaded…Apricot Pits?
Honey Intoxication
The DMSO Patient
Deadly Helium Balloons
The 2007 Pet Food Recall
Mercury in Vaccines and Eye Drops?
The World's Deadliest Frog
Leaded Candy
Why not Drink “Real” Root Beer?
The Killer Fog
Nail Polish or Nail Poison?
Game Board Danger
What Molecule Killed “Weird Al” Yankovic's Parents?
Deadly Popcorn
Even Water can be Poisonous
Chapter 4: Why Old Books Smell Good and Other Mysteries of Everyday Objects
The Smell of Old Books and the Hidden Vanilla Extract Underworld
That Smell Is You!
Electric Blue
The World's Most Abundant Organic Compound
Chalk Used to Be Alive
Decaffeinated? Try Deflavored!
Bad Blood
The Problem with Dry Cleaning
The Smell of Dead Fish
How to Make a Spark
The “New Car Smell”
A Gecko Cannot Stick to It!
Why Are Day Glow Colors and Highlighter Pens So Bright?
Why Your White Clothes Are not Really White?
How Can a Spray-on Sunscreen Be Dangerous?
There Is Ink in That Paper
Vomit and Sunless Tanners
Formaldehyde: Funerals, Flooring, and Outer Space
Further Reading
The Smell of Old Books and the Hidden Vanilla extract Underworld
That Smell is You!
Electric Blue
The World's Most Abundant Organic Compound
Chalk Used to be Alive
Decaffeinated? Try Deflavored!
Bad Blood
The Problem with Dry Cleaning
The Smell of Dead Fish
How to Make a Spark
The “New Car Smell”
A Gecko Can't Stick to it!
Why Are Day Glow Colors and Highlighter Pens So Bright? Why Your White Clothes are not Really White?
How Can Spray-On Sunscreen be Dangerous?
There is Ink in that Paper
Vomit and Sunless Tanners
Formaldehyde: Funerals, Flooring, and Outer Space
Chapter 5: Bath Salts and Other Drugs of Abuse
What Are the Dangers of Bath Salts?
What to Do If You Want Your Skin to Turn Blue
The Flesh-Rotting Street Drug
How Does a Breathalyzer Detect a Blood Alcohol Level?
How to Become a Brewery
How Was a Painkiller Used to Free Hostages?
The Secret Ingredient in Coca-Cola®
Why Is Crack Cocaine So Addicting?
Cocaine Smuggling versus Methamphetamine Manufacture
What Basic Common Ingredient Is Needed to Make the Drugs Vicodin®, Percocet®, Oxycontin®, and Percodan®?
Drug Money Is Right
What Percentage of Americans Use Prescription Drugs?
Are You Ready for Powdered Alcohol?
Ecstasy Is Ruining the Rain Forests
How Are Moldy Bread, Migraine Headaches, LSD, and the Salem Witch Trials All Related?
Further Reading
What are the Dangers of Bath Salts?
What to do If You Want Your Skin to Turn Blue
The Flesh-rotting Street Drug
How does a Breathalyzer Detect a Blood Alcohol Level?
How to Become a Brewery
How was a Painkiller Used to Free Hostages?
The Secret Ingredient in Coca-Cola®
Why is Crack Cocaine so Addicting? Cocaine Smuggling versus Methamphetamine Manufacture
What Basic Common Ingredient is Needed to Make the Drugs Vicodin®, Percocet®, Oxycontin®, & Percodan®?
Drug Money is Right
What Percentage of Americans use Prescription Drugs?
What is Powdered Alcohol?
Ecstasy is Ruining the Rainforests
How are Moldy Bread, Migraine Headaches, LSD, and the Salem Witch Trials all Related?
Chapter 6: Why Oil Is Such a Big Part of Our Lives
What Substance Is Used to Make 80 of All Pharmaceuticals?
Why Do Scientists Think Oil Comes From Fossilized Plants and Animals?
How Is Oil Made?
Where Is Most of the Carbon in the World?
The Most Widely Recycled Material in the United States
What Material Is Used to Make Asphalt?
How Oil Helped to Save the Whales
Further Reading
What Material is used to Make Roughly 80% of all Pharmaceuticals?
Why do Scientists Think Oil Comes from Fossilized Plants and Animals?
How is Oil Made? Where is Most of the Carbon in the World?
The Most Widely Recycled Material in the United States
What Material is used to Make Asphalt?
How Oil Helped to Save the Whales
Chapter 7: Why Junior Mints® Are Shiny and Other Weird Facts about Your Food
Why Is Gum Chewy?
The Problem with Gummi Bears
What Is the Easiest Way to Peel a Tomato?
Another Way to Eat Insect Parts!
Why Is High Fructose Corn Syrup More Consumed than Sugar?
What Causes Rancid Butter to Stink?
Why Does Mint Make Your Mouth Feel “Cold?”
It Is Probably Not Really Fresh Squeezed
Why Are Viruses Added to Some Sandwich Meat?
What Is Margarine Made From?
Why Are Junior Mints® Shiny?
Further Reading
Why is Gum Chewy?
The Problem with Gummi Bears
What is the Easiest Way to Peel a Tomato?
Another Way to Eat Insect Parts!
Why is High Fructose Corn Syrup More Consumed Than Sugar?
What Causes Rancid Butter to Stink?
Why Does Mint Make Your Mouth Feel “Cold?”
It's Probably Not Really Fresh Squeezed
Why are Viruses Added to Some Sandwich Meat?
What is Margarine Made From?
Why are Junior Mints Shiny?
Chapter 8: The Radioactive Banana and Other Examples of Natural Radioactivity
Where Does the Helium We Use in Balloons Come From?
Who Was the First Person to Win Two Nobel Prizes?
Where Is the Radioactive Material in YOUR House?
Which Elements Were First Detected in Radioactive Fallout from a Nuclear Bomb?
Radioactivity in Wristwatches, Exit Signs, and H-Bombs
The Earth Is One Giant Nuclear Reactor
Are Nuclear Reactors “Natural”?
Are Your Gemstones Radioactive?
Radon: The Radioactive Gas in Your Home
The Radioactive Banana
Further Reading
Where Does the Helium We Use in Balloons Come From?
The First Person to Win Two Nobel Prizes
Where is the Radioactive Material in YOUR House?
Which Elements were First Detected in Radioactive Fallout from a Nuclear Bomb?
Radioactivity in Wristwatches, Exit Signs, & H-Bombs
The Earth is One Giant Nuclear Reactor
Are Nuclear Reactors “Natural”?
Are Your Gemstones Radioactive?
Radon: The Radioactive Gas in Your Home
The Radioactive Banana
Chapter 9: Chemistry Is Explosive!
How Do Bullets Work?
What Is the Most Commonly Used Explosive in North America?
What Non-nuclear Substance Is the Most Explosive?
What Poison Is Used as an Explosive in Airbags?
Explosive Heart Medicine
Further Reading
How do Bullets Work?
The is the Most Commonly Used Explosive in North America
What Non-nuclear Substance is the Most Explosive?
What Poison is used as an Explosive in Airbags?
Explosive Heart Medicine
Chapter 10: The Chemistry in Breaking Bad and Other Popular Culture
How Does Methamphetamine Act as a Stimulant?
What Is “Pseudo,” and How Is It Related to Methamphetamine?
What Is Ricin?
The Thalidomide Disaster
What Is Phosphine Gas, and Why Is It a Potential Murder Weapon?
Acetylcholine, Pesticides, and Nerve Gas
Further Reading
How Does Methamphetamine Act as a Stimulant? What is “Pseudo,” and How is it Related to Methamphetamine?
What is Ricin?
The Thalidomide Disaster
What Is Phosphine Gas, and Why Is It a Potential Murder Weapon?
Acetylcholine, Pesticides, and Nerve Gas
Chapter 11: Why You Should Not Use Illegally Made Drugs: The Organic Chemistry Reason
Why You Shouldn't Use Illegally Made Drugs
The Tragic Case of the Frozen Addicts
Further Reading
Index
End User License Agreement
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Guide
Cover
Table of Contents
Preface
Begin Reading
List of Illustrations
Chapter 1: If You Do Not Know Any Chemistry, This Chapter Is For You
Figure 1.1 Look at what hides behind the door of understanding chemistry.
Scheme 1.1 The formation of an ionic bond in NaCl.
Figure 1.2 The structure of some simple molecules.
Figure 1.3 The condensed structure of some simple organic molecules.
Figure 1.4 The condensed structure of the benzene ring.
Figure 1.5 How polymers are represented.
Figure 1.6 Various neurotransmitters.
Figure 1.7 A representation of the lock-and-key model of receptors.
Figure 1.8 Molecules with structures similar to dopamine.
Figure 1.9 A representation of how dopamine and methamphetamine both fit in the dopamine receptor.
Figure 1.10 An example of a dipole intermolecular force.
Figure 1.11 An example of an instantaneous dipole intermolecular force.
Chapter 2: The Only True Aphrodisiac and Other Chemical Extremes
Figure 2.1 The structures of ethanol and GABA.
Figure 2.2 The structure of acetaminophen and its toxic metabolite, NAPQI.
Figure 2.3 Thiol containing compounds that react with NAPQI. The gray box highlights the thiol moiety.
Scheme 2.1 The reaction of NAPQI with the thiol in NAC.
Figure 2.2 The reaction of NAPQI with the thiol in a protein.
Figure 2.4 The structure of nicotine.
Figure 2.5 A comparison of the structures of nicotine and imidacloprid.
Figure 2.6 Apparently cockroaches do not care that nicotine is used as an insecticide.
Figure 2.7 A comparison of testosterone and a generic sterol structure.
Figure 2.8 The structure of caffeine.
Figure 2.9 A treatment for caffeine withdrawal.
Figure 2.10 The structure of aspirin.
Figure 2.11 A comparison of the structures of Denatonium benzoate and lidocaine.
Figure 2.12 A comparison of the structures of glucose and fludeoxyglucose.
Figure 2.13 The true structure of antimatter.
Figure 2.14 The structure of common biogenic volatile organic compounds.
Figure 2.15 The basic structure of graphene.
Figure 2.16 Layering of graphene sheets to form graphite.
Figure 2.17 A representation of graphene's strength.
Figure 2.18 The structure of phosgene.
Scheme 2.3 The reaction of phosgene with a protein.
Figure 2.19 A comparison of the structures of PVC, methylene chloride, and phosgene.
Scheme 2.4 The Haber process.
Figure 2.20 Explosives created using nitric acid.
Chapter 3: The Poisons in Everyday Things
Figure 3.1 A comparison of the structures of ethylene glycol and xylitol.
Scheme 3.1 The conversion of ethylene glycol to glycolic acid.
Figure 3.2 The structure of calcium oxalate.
Scheme 3.2 The conversion of glycolic acid to oxalic acid.
Scheme 3.3 The conversion of ethanol to acetic acid.
Figure 3.3 A comparison of the structures of butanediol and pentanediol.
Scheme 3.4 The conversion of butanediol to GHB.
Figure 3.4 A comparison of the structures of GHB, GABA, and 5-hydroxyvaleric acid.
Figure 3.5 The structure of tetrahydrozoline.
Figure 3.6 A helpful warning.
Figure 3.7 The structures of various salicylates.
Scheme 3.5 The synthesis of polycarbonate using bisphenol A.
Figure 3.8 A comparison of the structures of bisphenol A and estradiol.
Figure 3.9 A comparison of the structures of bisphenol A and bisphenol S.
Scheme 3.6 The decomposition of amygdalin.
Figure 3.10 The structure of laetrile.
Scheme 3.7 The synthesis of imitation benzaldehyde.
Scheme 3.8 The synthesis of methamphetamine using benzaldehyde.
Figure 3.11 The structure of a grayanotoxin.
Figure 3.12 A bear feeling the effects of honey intoxication.
Scheme 3.9 The conversion of DMSO to DMSO
4.
Figure 3.13 The structure of melamine and cyanuric acid.
Figure 3.14 The interaction of melamine and cyanuric acid. The hydrogen bonds are shown as dashed lines.
Figure 3.15 The interaction of cytosine and guanine. The hydrogen bonds are shown as dashed lines.
Figure 3.16 How melamine and cyanuric acid can combine to form a solid that causes kidney damage. The hydrogen bonds are shown as dashed lines.
Figure 3.17 The structure of thiomersal.
Figure 3.18 The structure of batrachotoxin.
Figure 3.19 The structures of safrole and 1′-hydroxysafrole.
Scheme 3.10 The conversion of 1′-hydroxysafrole to a reactive species.
Figure 3.11 The formation of a DNA adduct.
Figure 3.20 The toxic components of nail polish.
Figure 3.21 Nail polish or nail poison?
Figure 3.22 The structure of an urushiol and its quinone form.
Scheme 3.12 The reaction of the quinone form of an urushiol with a protein.
Figure 3.23 The structure of carbon monoxide.
Figure 3.24 The structure of diacetyl.
Figure 3.25 The movement of water during hyponatremia.
Chapter 4: Why Old Books Smell Good and Other Mysteries of Everyday Objects
Scheme 4.1 The synthesis of vanillin from lignin.
Figure 4.1 The structure of some of the molecules that produce the “Old Book” smell.
Scheme 4.2 The formation of “imitation” vanillin from guaiacol.
Figure 4.2 The structure of some of the molecules contained in vanilla extract.
Figure 4.3 The “Old Book” smell.
Figure 4.4 The structure of 1-octen-3-one.
Figure 4.5 A comparison of the structures of cellulose and starch.
Figure 4.6 Some of the molecules responsible for the flavor of coffee.
Figure 4.7 The structure of sugars found on the surface of red blood cells.
Figure 4.9 Another definition of a “universal donor.”
Figure 4.10 A Figure showing that water, ethanol, and sugar all contain –OH groups.
Figure 4.11 How cellulose fibers are held together by hydrogen bonds. The hydrogen bonds are dashed and highlighted in gray.
Figure 4.12 The structure of PERC.
Figure 4.13 The structure of carbon dioxide.
Scheme 4.3 The synthesis of TMA from TMAO.
Scheme 4.4 The synthesis of TMAA from TMA.
Figure 4.14 The structures of benzyl butyl phthalate and PVC.
Figure 4.15 The structure of some of the molecules found in the new car smell.
Figure 4.16 A comparison of the structures of polyethylene and Teflon.
Figure 4.17 Even a gecko cannot stick to a Teflon pan.
Figure 4.18 A representation of the fluorescence process in optical brighteners.
Figure 4.19 The structure of an optical brightener.
Figure 4.20 The structure of bisphenol A.
Scheme 4.5 The formation of the colored form of a leuko dye.
Figure 4.21 A comparison of the structures of DHA and glycerine.
Scheme 4.6 The formation of melanoidin pigments from DHA and proteins.
Figure 4.22 The structure of formaldehyde.
Figure 4.23 The structure of lysine.
Scheme 4.7 The reaction of proteins and formaldehyde.
Scheme 4.8 The reaction of DNA and formaldehyde to form damaged DNA.
Figure 4.24 Formaldehyde: interstellar traveler.
Chapter 5: Bath Salts and Other Drugs of Abuse
Figure 5.1 A comparison of the structures of cathinones and amphetamines.
Figure 5.2 Comparison of the structures of ecstasy and various bath salts.
Figure 5.3 The next generation of mephedrone bath salts.
Figure 5.4 The next generation of MDPV bath salts.
Figure 5.5 The structure of cysteine.
Scheme 5.1 The reaction of an Ag
+
and a protein.
Figure 5.6 The structure of silver sulfadiazine.
Figure 5.7 A comparison of the structures of krokodil and morphine.
Scheme 5.2 The conversion of codeine to krokodil.
Scheme 5.3 The oxidation ethanol to acetic acid.
Scheme 5.4 The reduction of oxygen to water.
Scheme 5.5 The overall reaction used to measure BAC by a breathalyzer.
Scheme 5.6 The conversion of ethanol to acetic acid.
Figure 5.8 Making the best out of auto-brewery syndrome.
Figure 5.9 Comparison of the structures of fentanyl, carfentanil, and oxycodone.
Figure 5.10 Comparison of cocaine–HCl and cocaine.
Scheme 5.7 The synthesis of crack using baking soda.
Scheme 5.8 The synthesis of methamphetamine from pseudoephedrine.
Figure 5.11 A comparison of the structures of opioids.
Figure 5.12 Molecules that come from the opium poppy.
Figure 5.13 The structure of dextrin.
Figure 5.14 Comparison of molecules which are similar in structure to MDMA.
Scheme 5.9 The conversion of safrole to ecstasy.
Figure 5.15 Comparison of the structures of ergometrine, lysergic acid, and LSD.
Scheme 5.10 The conversion of ergotamine to LSD.
Figure 5.16 A comparison of hallucinogenic molecules that mimic the structure of serotonin.
Chapter 6: Why Oil Is Such a Big Part of Our Lives
Scheme 6.1 The synthesis of Aspirin using Benzene obtained from petroleum.
Figure 6.1 The structure of quinine, aniline, and mauveine.
Figure 6.2 The structure of some basic petrochemicals.
Scheme 6.2 The synthesis of TNT using heptane obtained from petroleum.
Figure 6.3 All of these drugs are made from molecules obtained from petroleum.
Figure 6.4 A comparison of a vanadium containing porphyrin found in crude oil and chlorophyll.
Figure 6.5 The structure of a kerogen fragment. The word “core” represents a connection to a larger molecular matrix.
Figure 6.6 The average molecular structure of molecules found in asphalt.
Figure 6.7 The structure of oleic acid, a fatty acid.
Scheme 6.3 The decomposition of triglycerides to form glycerine and fatty acids.
Chapter 7: Why Junior Mints® Are Shiny and Other Weird Facts about Your Food
Figure 7.1 The structure of isoprene.
Scheme 7.1 The conversion of isopentenyl diphosphate into latex.
Figure 7.2 A comparison of the structures of polymers typically found in gum base.
Figure 7.3 You can thank chemistry for this situation.
Figure 7.4 The structure of glycine and proline.
Figure 7.5 Showing how water becomes imbedded in collagen. Hydrogen bonds are dashed.
Figure 7.6 The structure of carminic acid.
Figure 7.7 The structure of kermesic acid.
Figure 7.8 The structure of sucrose.
Scheme 7.2 The conversion of starch to glucose.
Figure 7.3 The conversion of glucose to fructose.
Figure 7.9 No it does not.
Scheme 7.4 The conversion of a triglyceride into glycerine and fatty acids.
Figure 7.10 The structure of some fatty acids found in butter.
Figure 7.11 A comparison of carboxylic acids that smell bad.
Figure 7.12 The structure of triclosan.
Scheme 7.5 The conversion of leucine into isovaleric acid.
Figure 7.13 The structure of capsaicin and eugenol.
Figure 7.14 A comparison of molecules that activate TRPM8 nerve receptors.
Figure 7.15 The structure of icilin.
Figure 7.16 The structures of ethyl butyrate and limonene.
Figure 7.17 The structure of a typical bacteriophage.
Figure 7.18 Bacteriophages make a great sandwich condiment.
Figure 7.19 A comparison of the packing of saturated and unsaturated chains.
Figure 7.20 A comparison of the structure of a saturated fat and a wax.
Scheme 7.6 The removal of a double bond using hydrogenation.
Figure 7.21 The cis- and trans-configurations of a double bond.
Figure 7.22 The structures of aleuritic acid and shellolic acid.
Figure 7.24 Why they call it confectioner's glaze.
Chapter 8: The Radioactive Banana and Other Examples of Natural Radioactivity
Scheme 8.1 The alpha particle decay of uranium-238.
Scheme 8.2 An alpha particle gaining two electrons to become helium gas.
Figure 8.1 A clown holding balloons filled with radioactive decay (helium).
Scheme 8.3 The alpha particle decay of americium-241.
Scheme 8.4 The absorption of uranium-235 to form uranium-236.
Figure 8.5 The fission of uranium-236.
Scheme 8.6 The formation of einsteinium by neutron bombardment of uranium-238.
Figure 8.7 The formation of fermium by neutron bombardment of uranium-238.
Figure 8.2 Even an atomic bomb can cause chemical reactions.
Scheme 8.8 The beta particle decay of tritium.
Scheme 8.9 The formation of tritium by the neutron bombardment of lithium-6.
Scheme 8.10 The fusion reaction that creates a nuclear explosion.
Scheme 8.11 The alpha particle decay of uranium-238.
Scheme 8.12 The alpha particle decay of radon-222.
Figure 8.3 Even cavemen are concerned about radon.
Scheme 8.13 The beta particle decay of potassium-40.
Figure 8.4 The radioactive banana.
Chapter 9: Chemistry Is Explosive!
Scheme 9.1 The combustion of methane.
Figure 9.1 The structure of a N
2
molecule.
Figure 9.2 The structures of C4, TNT, and nitroglycerin.
Scheme 9.2 The chemical reaction of gun powder.
Figure 9.3 A bullet being pushed to over 1000 mph by the mighty N
2
molecule.
Scheme 9.3 The unbalanced chemical reaction of ANFO.
Figure 9.4 A comparison of the structures of cubane and octanitrocubane.
Figure 9.5 The structure of sodium azide.
Scheme 9.4 The reaction of sodium azide.
Figure 9.6 The structures of potential sodium azide substitutes.
Scheme 9.5 The chemical reaction of nitroglycerin.
Figure 9.7 A comparison of the structures of glycerin, nitroglycerin, and amyl nitrite.
Figure 9.8 An unusual source of nitroglycerin.
Chapter 10: The Chemistry in Breaking Bad and Other Popular Culture
Figure 10.1 A comparison of the structures of dopamine and methamphetamine.
Figure 10.2 A comparison of molecules that are structurally similar to methamphetamine.
Figure 10.3 A comparison of the structures of pseudoephedrine and adrenaline.
Scheme 10.1 The synthesis of methamphetamine from pseudoephedrine.
Figure 10.4 Sadly, a true story.
Scheme 10.2 The synthesis of methamphetamine from phenylacetone.
Figure 10.5 A comparison of the structures of right- and left-handed thalidomides.
Figure 10.6 The structure of phosphine.
Figure 10.7 The structure of acetylcholine.
Figure 10.8 The structure of succinylcholine.
Scheme 10.3 The decomposition of acetylcholine.
Figure 10.9 The structures of some organophosphate insecticides.
Figure 10.10 The structure of phosmet.
Figure 10.11 A comparison of the structures of VX and sarin.
Scheme 10.4 The inactivation of acetylcholinesterase with Sarin gas.
Scheme 10.5 The reactivation of acetylcholinesterase with pralidoxime.
Chapter 11: Why You Should Not Use Illegally Made Drugs: The Organic Chemistry Reason
Figure 11.1 A comparison of the structures of MPPP and meperidine.
Scheme 11.1 The formation of MPTP from MPPP.
Scheme 11.2 The decomposition of meperidine.
Figure 11.2 A comparison of the structures of MPTP and MPP+.
Figure 11.3 A comparison of the structures of dopamine and l-Dopa.
List of Tables
Chapter 1: If You Do Not Know Any Chemistry, This Chapter Is For You
Table 1.1 Some common ionic compounds
Chapter 2: The Only True Aphrodisiac and Other Chemical Extremes
Table 2.1 A comparison of the lethal doses of toxic compounds
Chapter 4: Why Old Books Smell Good and Other Mysteries of Everyday Objects
Table 4.1 The compatibility of different blood groups
Chapter 9: Chemistry Is Explosive!
Table 9.1 A comparison of the R.E. factors of various explosives
Strange Chemistry
The Stories Your Chemistry Teacher Wouldn't Tell You
Steven Farmer
Sonoma State University, Rohnert Park, California, USA
This edition first published 2017
© 2017 John Wiley & Sons, Inc.
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Library of Congress Cataloging-in-Publication Data
Names: Farmer, Steven C., author.
Title: Strange chemistry : the stories your chemistry teacher wouldn't tell you / by Steven Farmer.
Description: Hoboken, NJ : John Wiley & Sons, 2017. | Includes bibliographical references and index.
Identifiers: LCCN 2017016092 (print) | LCCN 2017026188 (ebook) | ISBN 9781119265290 (pdf) | ISBN 9781119265283 (epub) | ISBN 9781119265269 (pbk.)
Subjects: LCSH: Chemistry-Popular works.
Classification: LCC QD37 (ebook) | LCC QD37 .F37 2017 (print) | DDC 540-dc23 LC record available at https://lccn.loc.gov/2017016092
Paperback ISBN: 9781119265269
Cover image: Courtesy of the author; (Background) © P Wei/iStockphoto
Cover design by Wiley
Dedication
I would like to dedicate this book to my parents James and Margaret.
Throughout my whole life whenever I looked, you were there; ready to give me love and support, guidance and security, and praise and encouragement. You filled me with your dreams and showed me what it takes to succeed in life. Without you both none of the things I have accomplished would have been possible. I am truly blessed to have such incredible parents, and I love you both.
Preface
Growing up in Northern California was much more curious than one might think. Napa, being part of Northern California, was affected by the LSD (lysergic acid diethylamine) counterculture centered in Berkeley and San Francisco. LSD was everywhere and I recall multiple instances in high school where a classmate would admit to attending class under the influence of LSD and try to describe the effects. This seems very rebellious, but in one of the most tragic events of my life, a high school friend jumped in front of a car on the highway after ingesting LSD. He was killed instantly. This event had such a profound effect on me that it eventually drove me toward a career in chemistry – I needed to understand what had happened to my friend. How could the ingestion of a molecule cause such profound effects? Is awareness really just a fragile chemical process that can be so easily tricked?
After the mass closures of the 1980s, Napa State Hospital was one of the few remaining state run mental hospitals in California. If you have seen the movie One Flew Over the Cuckoo's Nest, it was filmed at Napa State Hospital. As a child, I would often wonder about the causes of mental illness. I was told that mental illness was the result of a “chemical imbalance” in the brain, but what did that really mean? Could a slight change in a chemical really change our perception of the world?
Similar to many scientists before me, my career in chemistry was driven by a quest to better understand some of the questions that haunted my childhood. Surely, obtaining a degree in chemistry would allow me to understand how hallucinogens work, or what causes mental illnesses. Unfortunately, I was wrong. Chemistry courses seemed to steer clear of any topic of an edgy, dangerous, or unusual nature. In fact, initially learning about these fascinating topics required a course outside the chemistry department. Eventually, a graduate elective course from a psychology department, called “Psychopharmacology,” explained the chemical basis for the effect of hallucinogens and the causes of mental illness (I share what I learned in this book).
Later, when I became a chemistry instructor, I made it a point to share these and other stories. It was delightful to find that almost everyone found these topics just as interesting as I did. As I collected new stories, I realized how much of this material was never discussed as part of the numerous chemistry courses required for my Ph.D. Roughly 90% of these stories contained in this book were learned after I graduated. This is where the subtitle of this book, “The stories your chemistry teacher wouldn't tell you” comes from. It seems that there is an overwhelming push to teach the fundamentals of chemistry while neglecting to show the utility of learning the material by connecting it to the real world. Particularly for organic chemistry, there seems to be an aversion of some of these topics, which I feel is because chemists do not want their science associated with anything that poisons you, blows you up, or gets you high. However, these are the topics that many people find exciting (as can be seen by looking at the plot of almost any action movie). Ask a nonchemist where chemicals appear in everyday life and inevitably the answer involves pharmaceuticals, toxins, or illicit drugs.
To share these stories with my students, I usually would take about 5–10 minutes each week to present one of the stories described in this book. For those of you who are teachers or who plan to be, I can say that these stories have been the largest source of positive feedback I have received from my students. Although there is an enormous amount of material that needs to be covered in a typical chemistry course, I say make the time for these extras. It is that important! On multiple occasions, students admitted to me that they only came to class that day so that they could hear the story. Many times, students would speak to me after the lecture to share how that day's story had touched them in some way. One student had been to the emergency room for an acetaminophen overdose, another had a stepfather who was addicted to opioids, and yet another was prescribed amphetamine to treat their attention deficit hyperactivity disorder (ADHD).
You will note that most of the presented stories are short and involve a question or a defined idea. This is done for two reasons: First, I love presenting these questions to my students and trying to evoke an answer from them. Putting students on the spot drives home how little they actually know about the world and how learning chemistry helps them understand their lives. I admit, few things have made me feel more educated than seeing a single simple question stump a classroom with over 400 students. Try it. You will find that very few people know the answers to the questions posed in this book. In addition, some of the cheeky answers I receive have become the highlights of my teaching. Second, I present the stories in a simple format because they will be easy to remember. Jokingly, I tell students to share these stories with their friends and family members so that they can prove that they are receiving an education at Sonoma State University. I am pleased to say that they do just that. An informal poll of my students showed that 90% of them had shared a story at least once, and 75% said that they shared these stories on a regular basis.
Students, like all human beings, want to understand the world around them – they may just not realize it. Telling stories that help students understand and connect to the world they see inspires them in a primal way, making them want to learn and keep coming back for more. This book contains the best stories I have collected over the last 10 years. If you are a teacher, try some of them out and see the profound effect they have on students. Even if you are not a teacher, read on, better understand the world around you, and see how truly strange chemistry can be.
Acknowledgments
To my loving wife, Joy: You are still the most beautiful woman I have ever seen. You are my muse, my life, and the air that I breathe. You are the personification of everything that makes me happy in this world. It was only your love that allowed me to face the adversity I have seen. You have been with me since the start of this journey and I cannot wait to see where life takes us.
To my brother, Richard: Thanks for being the oldest friend I have and for being the funniest person I know.
To my first college chemistry professor, Dr Steven Fawl: Thanks for all of those long talks in your office. Thanks for taking time out for someone who had absolutely no idea what he was going to do with his life. Of all my science professors, you seemed the most worldly and grounded. Your knowledge of chemistry seemed to let you understand the world and how it works. It was because of you that I decided to become a chemist.
To the students of Sonoma State University: Thanks for listening to all of my crazy stories and for continually reminding me why I love teaching so much.
To my colleagues in the chemistry department: Thanks for your help in vetting these stories.
To my agent, Priya Doraswamy of Lotus Lane Literary (lotuslit.com): Thanks for being one of the nicest people I have ever worked with and for helping me realize my dream.
To my editor, Christine Miller (http://tellmewhatyouwanttosay.com): Thanks for all of your encouragement and for helping me find my voice.
To Michelle Sanner: Thanks for your help with the acetaminophen story and helping to start me down the chemical education path.
Chapter 1If You Do Not Know Any Chemistry, This Chapter Is For You
As a professor, I regularly teach college-level chemistry courses. These courses present various materials, which are important for students who wish to continue their careers in chemistry. Although most people reading this book will not need all the information covered in these courses, understanding a few key concepts will allow them to understand various ways in which chemistry shows up in everyday life. In fact, one of the driving forces of compiling these stories is to show that even a basic understanding of chemistry can help us comprehend how the world and society work. In particular, I would like to bring readers up to speed on a few key chemical concepts that are referred to in this book (Figure 1.1).
Figure 1.1 Look at what hides behind the door of understanding chemistry.
Representing Atoms and Molecules in Chemistry
The first concept concerns the representation of atoms and molecules. Often, the structure of molecules can provide insight into its properties or the ways in which it will affect a human being, if ingested. Certain structural features will imbue molecules with particular properties. In addition, molecules with similar structures will often have similar properties. A detailed understanding of chemistry is not required to make this connection, but only the ability to see similarities.
Chemists represent an individual element with a capital letter, such as “C” for carbon, “H” for hydrogen, and “Fe” for iron, as listed in a periodic table. This letter represents all of the protons and neutrons in the atom's nucleus plus any electrons not involved in bonding. During most chemical reactions, the nucleus of atoms remains unchanged, so this simple representation of elements is helpful to chemists. If an oxygen atom is involved in a chemical reaction, it will remain an oxygen atom. Its structure and bonding may change, but the nucleus will be the same. An important exception is radioactive decay, where a nucleus can be changed and one element can change into another. This will be discussed later.
In the case of some metals and gases, the atom is not bonded (connected) to any other atoms; hence, the bulk material can be represented with the elemental symbol. A block of iron is made up entirely of iron atoms that can be represented by symbol Fe. Similarly, a balloon filled with helium can represented with the symbol He.
Although individual elements are important, chemistry truly becomes interesting when atoms start bonding together to form more complex structures. Two major types of bonds are ionic and covalent. In an ionic bond, one atom gives up one or more electrons, giving it a positive charge, while another atom gains one or more electrons, giving it a negative charge. Electrostatic forces bring the positive and negative ions together. However, when ionic compounds are placed in an appropriate solvent, such as water, the compounds break apart into their ionic species. The classic ionic compound is common table salt sodium chloride (NaCl). In the crystals of table salt, the sodium and chlorine atoms are being held together by the attraction of a positive and negative charge. When placed in water, table salt tends to break apart into its ionic species, in this case Na+ and Cl− (Scheme 1.1).
Scheme 1.1 The formation of an ionic bond in NaCl.
Ionic compounds are generally made with ionic bonds. Ionic bonds are easily identified because they are made by combining a metal (elements on the left-hand side of the periodic table) with a nonmetal (elements found in the upper right-hand corner of the periodic table). Ionic bonds are typically not formally drawn; rather, the ions are drawn together in a molecular formula where the overall compound is neutral. For example, FeCl3 means a Fe3+ ion bonds to three Cl− ions using ionic bonds. This simple discussion will allow for a better understanding of many ionic compounds with which you may be familiar (Table 1.1).
Table 1.1 Some common ionic compounds
Compound
Name
Ions involved
Common use
KI
Potassium iodide
K
+
& I
−
Treatment of hyperthyroidism
PbO
2
Lead (IV) oxide
Pb
+4
& O
−2
Found in car batteries
CaCl
2
Calcium chloride
Ca
+2
& Cl
−
Road deicing
Covalent bonds differ from ionic bonds in that electrons are shared rather than stolen to form a bond between two atoms. This means that covalent bonds are not easily broken into ionic species and do not break apart when dissolved in water. The sharing of two electrons between two atoms to form a covalent bond is represented with a single line. The water molecule is made up of two H−O single covalent bonds. Similarly, if four electrons are shared between two atoms, the covalent bond is shown with a double line and is called a double bond. Six shared electrons are depicted by three lines and called a triple bond. Molecular oxygen is made up of a double bond between the two oxygen atoms, and molecular nitrogen is made up of a triple bond between the two nitrogen atoms. Single, double, and triple bonds all have different properties and reactivity that are dependent on the types of atoms involved in the covalent bond. Even now, this basic description of covalent bonds can help you understand the structure of multiple simple molecules (Figure 1.2).
Figure 1.2 The structure of some simple molecules.
What makes covalent bonds so interesting is their ability to combine to form large molecular structures. Inorganic compounds do not have this ability. Literally, thousands of atoms can be linked together by covalent bonds to create such complex molecules as polymers, proteins, and even deoxyribonucleic acid (DNA).
This book focuses mostly on organic molecules, which are typically constructed with covalent bonds. Organic molecules were originally called “organic” because it was believed that these types of compounds could only come from living, organic sources, such as plants or animals. Once it was shown that organic molecules could be made from inorganic materials, the definition was expanded. The current definition states that organic molecules contain the element carbon. Organic chemistry is the study of carbon-containing molecules. For the purposes of this book, we will be focusing on the conversion of one organic molecule into another using reactions. Using these reactions, organic chemists create many pharmaceuticals, many plastics, and a multitude of other molecules.
The versatility of covalent bonds creates virtually limitless possible combinations of organic molecules, which is why organic chemistry is such a broad field of study. In college, an entire year of study is devoted to organic chemistry to obtain a typical chemistry degree. At this point, millions of organic compounds are known, with new ones being generated every day. One of the more interesting aspects of organic chemistry is the ability to combine atoms in new ways to make new organic molecules, many of which have never been seen in nature.1
Because of the large numbers of variations, organic molecules are commonly represented by structures as well as their formal names. In addition, due to a large and complex nature of organic molecules, they are often drawn using a condensed form. Because organic molecules typically have a large number of hydrogens in their structures, it is particularly common to represent hydrogens in an abbreviated form. In a condensed structure, the bonds attached to the hydrogens are omitted and the number of H's is represented with a subscript. Examples of these abbreviations are represented below using some simple organic molecules (Figure 1.3).
Figure 1.3 The condensed structure of some simple organic molecules.
Another important way in which hydrogens are abbreviated involves the benzene ring. This ring is immensely important in organic chemistry, and its presence can be seen in many important organic molecules. To simplify the structure, the hydrogens at the points of the benzene ring are commonly omitted. Moreover, the carbon atoms in the benzene ring are represented simply by lines denoting the covalent bonds (Figure 1.4).
Figure 1.4 The condensed structure of the benzene ring.
Lastly, the structures of polymers are usually represented using a type of abbreviation. Small molecules called monomers are connected in large numbers during a polymerization reaction to create large molecules called polymers. This process is represented in the name “polymer,” which means many monomers. Because polymers are made up of a repeating monomer subunit, they are represented by the subunit surrounded by brackets. The monomer subunit is repeated a variable number of times, which is represented by the subscript “n.” The actual number of monomers subunits in a polymer is usually unknown, which is why it is represented by a variable (Figure 1.5).
Figure 1.5 How polymers are represented.
Neurotransmitters
In this book, neurotransmitters are the most important molecules used to describe the function of organic molecules in the body. Virtually everything we do involves neurons communicating with one another. Everything from movement, breathing, and even awareness are brought about by electrical impulses moving across our nervous system. Anyone who has seen a Taser in action knows that neurons are affected by electricity; however, certain chemicals also play an important role in how neurons operate. Many neurons are separated by a small gap called the synaptic cleft. During a typical nerve impulse, specific molecules called neurotransmitters bridge this gap. When an electrical impulse reaches the end of a presynaptic neuron, neurotransmitters are released and subsequently diffused across the synaptic cleft, binding to the receptors on the receiving postsynaptic neuron. Receptors are typically proteins on the surface of the neurons, which recognize and bind to specific neurotransmitters. This binding usually brings about a chemical change that creates an electrical impulse in the receiving postsynaptic neuron. In short, neurotransmitters allow for electrical impulses to be transmitted between adjacent neurons despite the presence of a synaptic gap. By repeating this process, electrical nerve impulses can be sent across the body or across the brain. Neurotransmitters that cause a neuron to fire are considered “excitatory” and are responsible for motion, mental cognition, and other activities that require the brain and body to be active (Figure 1.6).
Figure 1.6 Various neurotransmitters.
In addition, certain neurotransmitters can also be “inhibitory” and actually impede the transmission of impulses in neurons. The effect of inhibitory neurotransmitters in these neurons causes a chemical change within the neuron that opposes the effects of excitatory neurotransmitters. In general, inhibitory neurotransmitters are responsible for inducing sleep and filtering out unnecessary excitatory signals.
In short, neurotransmitters send chemical messages between neurons and act as the on and off switches of the nervous system. By understanding that chemicals can affect how neurons work, many interesting concepts can be discussed. Many mental illnesses are believed to be caused by a “chemical imbalance” of neurotransmitters in certain areas of the brain. Many medications used to treat mental illnesses, as well as many psychoactive drugs and neurotoxins, obtain their effects by changing the ways in which neurotransmitters are released and absorbed or by simply mimicking the structure of a neurotransmitter. The key receptors in neurons designed to recognize neurotransmitters look for specific structural features. This is called the lock-and-key model. Receptors proteins are typically wadded into a ball-like structure that has small pockets. Certain structural features of molecules allow them to fit into these pockets, activating the receptors. Because the receptors are looking for specific structural features, molecules that have similar structural features can fool these receptors (Figure 1.7).
Figure 1.7 A representation of the lock-and-key model of receptors.
Figure 1.8 Molecules with structures similar to dopamine.
Figure 1.9 A representation of how dopamine and methamphetamine both fit in the dopamine receptor.
An excellent example is seen with the molecules dopamine and methamphetamine. Dopamine is one of the most important neurotransmitters in the parts of the brain involving motion and alertness. Key receptors in neurons recognize the benzene ring connected to two carbons and a nitrogen found in dopamine. Methamphetamine also has a benzene ring connected to two carbons and nitrogen, so it can also fit into these receptors, which tricks the neurons into thinking that it is dopamine. The presence of methamphetamine causes the areas of the brain, which utilize dopamine to become excited, causing the hyperactivity and insomnia associated with methamphetamine use. Now that we understand the structural features that can allow molecules to mimic dopamine, we can look for them in other molecules. Ritalin® has these structural features, and it is used to treat attention deficit hyperactivity disorder (ADHD) by stimulating the parts of the brain associated with attention. In addition, the common decongestant pseudoephedrine has these structural features and has the side effects of causing restlessness and insomnia, which has to be stated on the packaging (Figures 1.8 and 1.9).
Intermolecular Forces
Have you ever wondered why some molecules like oxygen are a gas at room temperature and ambient pressure while other molecules like water are liquid and still others like table salt (NaCl) are a solid? This has to do with a concept called intermolecular forces (IMF) or the forces between individual molecules. In general, molecules with relatively strong IMFs tend to hold together better and form solids and those with weak IMFs tend not to hold together and form gases. Having a basic understanding of IMFs allows one to have a better understanding of the world. Why a solid is a solid, why does one substance stick to another, and why do some liquids mix while others separate into layer?
To have a basic understanding of IMFs, you just have to remember that positive and negative charges are attracted to each other. The ways in which these positive and negative charges are generated in molecules determine the strength of the IMFs between them.
This book discusses four major IMFs. The strongest is called the ionic IMF. As discussed previously, when a compound contains an ionic bond, one or more electrons are shared to form positive and negatively charged species. These charged species are then attracted to each other by the ionic IMF. These compounds, which contain ionic bonds (metals bonded to nonmetals), are typically solids under normal conditions. Salts, such as common table salt (NaCl) or potassium chloride (KCl), as well as most minerals, such as chalk (CaCO3) and iron pyrite (FeS), all contain ionic bonds and ionic IMFs.
The next strongest IMF is called a dipole IMF. Dipole IMFs are typically found when dealing with molecules containing covalent bonds. Although it is possible for organic compounds to have ionic IMFs, most are governed by dipole IMF's. In a covalent bond, electrons are being shared by two atoms, although they are rarely shared equally. Electronegativity is a measure of an atom's ability to pull on the electrons in a covalent bond. The elements of the periodic table typically become more electronegative as we travel up and to the right of the table, with fluorine being the most electronegative element. There are many exceptions to this rule, but it is a general trend. In the molecule ICl, the electrons in the I−Cl covalent bond are drawn closer to the chlorine because it is more electronegative than iodine. This gives the chlorine a partial negative charge, which is represented by the symbol δ−. This also gives the iodine a partial positive charge represented by the symbol δ+. The ICl molecule is called polar because one side of a molecule has a slight positive charge and the other side has a slight negative charge. A dipole IMF is created when the positive side on one molecule is attracted to the negative side of an adjacent molecule. The molecule ICl has only one covalent bond; however, molecules with multiple covalent bonds can also be polar, depending on the orientations of the bonds and the electronegativity of the atoms involved. Note! The dipole IMF is weaker compared to the ionic IMF because only partial charges are being used (Figure 1.10).
Figure 1.10 An example of a dipole intermolecular force.
An important subset of dipole IMFs is called hydrogen bonding, and it is reserved for some of the most electronegative elements in the periodic table, like nitrogen, oxygen, and fluorine. When these elements are directly bonded to hydrogen in a molecule, this special IMF comes about. In this case, the charge separation caused by these highly electronegative elements is so extreme that dipole interaction is enhanced. The hydrogens are “loose” and do not remain permanent bonded. They freely move around, and they can be shared by other hydrogen-bonding molecules. This causes a hydrogen-bonding interaction, which is stronger compared to a typical dipole interaction. Many common liquids utilize hydrogen-bonding IMFs, including water and alcohol. In addition, DNA strands are held together using hydrogen bonding.
The last IMF is probably the most difficult to conceive, although it is still extremely important. Covalent bonds involve electrons being shared; therefore, they are affected by the electronegativity of the atoms involved. However, what happens when the two atoms are the same? A prime example of this is an oxygen molecule. The two oxygen atoms have exactly the same electronegativity, therefore, exactly the same pull on the electrons in the covalent bond. There is no separation of charge; thus, the molecule is deemed nonpolar. This can also come about when dealing with substances that have no bonds, such as helium, or with molecules that orientate their bonds so that there is no charge separation in the molecule, such as methane. All these molecules are also considered nonpolar; however, the fact that they can form liquids when made cold enough shows that there must be some type of IMF in them. This last and weakest IMF has many names, including instantaneous dipole forces, Van der Walls forces, and dispersion forces. I will call them instantaneous dipoles in this book because I feel this name best describes the effect.
Instantaneous dipole IMFs can best be explained by looking at a typical helium atom. It is made up of a nucleus containing two protons and two neutrons surrounded by two elections. The two negatively charged electrons balance out the two positively charged protons in the nucleus so the overall atom is neutral. Because both electrons are negatively charged, they repel each other and usually stay on the opposite sides of the nucleus. However, these electrons orbit the nucleus at extremely fast speeds, roughly 80% the speed of light; hence, it is possible for these electrons to crowd on one side of the helium atom. When this happens, the nucleus is momentarily exposed, giving the atom a positively charged side (δ+) while the crowded electrons give the other side of the atom a negative charge (δ−
