Organic Chemistry 5th Edition by Janice Gorzynski Smith
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LanguageEnglish
Pages1369
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Organic Chemistry 5th Edition by Janice Gorzynski Smith



Organic Chemistry 5th Edition by Janice Gorzynski Smith | PDF Free Download.

Author of Organic Chemistry PDF


Janice Gorzynski Smith

Smith was born in Schenectady, New York. She became interested in chemistry in high school and went on to major in chemistry at Cornell University, where she received an A.B. degree summa cum laude.

Jan earned a Ph.D. in Organic Chemistry from Harvard University under the direction of Nobel Laureate E. J. Corey, and she also spent a year as a National Science Foundation National Needs Postdoctoral Fellow at Harvard. During her tenure with the Corey group, she completed the total synthesis of the plant growth hormone gibberellic acid.

Following her postdoctoral work, Jan joined the faculty of Mount Holyoke College, where she was employed for 21 years.

During this time she was active in teaching organic chemistry lecture and lab courses, conducting a research program in organic synthesis, and serving as department chair.

Her organic chemistry class was named one of Mount Holyoke’s “Don’tmiss courses” in a survey by Boston magazine. After spending two sabbaticals amidst the natural beauty and diversity in Hawai‘i in the 1990s, Jan and her family moved there permanently in 2000.

She is currently a faculty member at the University of Hawai‘i at Mānoa, where she teaches the two-semester organic chemistry lecture and lab courses.

In 2003, she received the Chancellor’s Citation for Meritorious Teaching. Jan resides in Hawai‘i with her husband Dan, an emergency medicine physician, pictured with her hiking in New Zealand in 2015. She has four children and three grandchildren.

When not teaching, writing, or enjoying her family, Jan bikes, hikes, snorkels, and scuba dives in sunny Hawai‘i, and time permitting, enjoys travel and Hawaiian quilting.

Organic Chemistry Contents


  • Structure and Bonding 
  • Acids and Bases
  • Introduction to Organic Molecules and Functional Groups
  • Alkanes 
  • Stereochemistry 
  • Understanding Organic Reactions 
  • Alkyl Halides and Nucleophilic Substitution
  • Alkyl Halides and Elimination Reactions 
  • Alcohols, Ethers, and Related Compounds
  • Alkenes 
  • Alkynes
  • Oxidation and Reduction
  • Mass Spectrometry and Infrared Spectroscopy 
  • Nuclear Magnetic Resonance Spectroscopy 
  • Radical Reactions
  • Conjugation, Resonance, and Dienes 
  • Benzene and Aromatic Compounds 
  • Reactions of Aromatic Compounds 
  • Carboxylic Acids and the Acidity of the O–H Bond 
  • Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction
  • Aldehydes and Ketones—Nucleophilic Addition 
  • Carboxylic Acids and Their Derivatives—Nucleophilic Acyl Substitution
  • Substitution Reactions of Carbonyl Compounds at the α Carbon
  • Carbonyl Condensation Reactions
  • Amines
  • Carbon-Carbon Bond-Forming Reactions in Organic Synthesis
  • Pericyclic Reactions 
  • Carbohydrates 
  • Amino Acids and Proteins 
  • Synthetic Polymers 
  • Lipids 1231 (Available online)

Preface to Organic Chemistry eBook


Organic chemistry. You might wonder how a discipline that conjures up images of eccentric old scientists working in basement laboratories is relevant to you, a student in the twenty-first century. Consider for a moment the activities that occupied your past 24 hours.

You likely showered with soap, drank a caffeinated beverage, ate at least one form of starch, took some medication, listened to a CD, and traveled in a vehicle that had rubber tires and was powered by fossil fuels. If you did any one of these, your life was touched by organic chemistry.

What Is Organic Chemistry?

Organic chemistry is the chemistry of compounds that contain the element carbon.

It is one branch in the entire field of chemistry, which encompasses many classical subdisciplines including inorganic, physical, and analytical chemistry, and newer fields such as bioinorganic chemistry, physical biochemistry, polymer chemistry, and materials science.

Organic chemistry was singled out as a separate discipline for historical reasons. Originally, it was thought that compounds in living things, termed organic compounds, were fundamentally different from those in nonliving things, called inorganic compounds.

Although we have known for more than 150 years that this distinction is artificial, the name organic persists.

Today the term refers to the study of the compounds that contain carbon, many of which, incidentally, is found in living organisms. It may seem odd that a whole discipline is devoted to the study of a single element in the periodic table when more than 100 elements exist. It turns out, though, that there are far more organic compounds than any other type.

Organic chemicals affect virtually every facet of our lives, and for this reason, it is important and useful to know something about them.

Clothes, foods, medicines, gasoline, refrigerants, and soaps are composed almost solely of organic compounds. Some, like cotton, wool, or silk are naturally occurring; that is, they can be isolated directly from natural sources.

Others, such as nylon and polyester, are synthetic, meaning they are produced by chemists in the laboratory. By studying the principles and concepts of organic chemistry, you can learn more about compounds such as these and how they affect the world around you. Realize, too, what organic chemistry has done for us.

Organic chemistry has made available both comforts and necessities that were previously nonexistent or reserved for only the wealthy. We have seen an enormous increase in life span, from 47 years in 1900 to over 70 years currently.

To a large extent, this is due to the isolation and synthesis of new drugs to fight infections and the availability of vaccines for childhood diseases.

Chemistry has also given us the tools to control insect populations that spread disease, and there is more food for all because of fertilizers, pesticides, and herbicides. Our lives would be vastly different today without the many products that result from organic chemistry (Figure 1).

Organic chemistry has given us contraceptives, plastics, antibiotics, and the knitted material used in synthetic heart valves.

Some Representative Organic Molecules

Perhaps the best way to appreciate the variety of organic molecules is to look at a few. Three simple organic compounds are methane, ethanol, and trichlorofluoromethane. 

Methane, the simplest of all organic compounds, contains one carbon atom. Methane the main component of natural gas occurs widely in nature. Like other hydrocarbons organic compounds that contain only carbon and hydrogen methane are combustible; that is, it burns in the presence of oxygen.

Methane is the product of the anaerobic (without air) decomposition of organic matter by bacteria. The natural gas we use today was formed by the decomposition of organic material millions of years ago. Hydrocarbons such as methane are discussed in Chapter 4. 

Ethanol, the alcohol present in beer, wine, and other alcoholic beverages, is formed by the fermentation of sugar, quite possibly the oldest example of organic synthesis. Ethanol can also be made in the lab by a totally different process, but the ethanol produced in the lab is identical to the ethanol produced by fermentation. Alcohols including ethanol are discussed in Chapter 9. 

Trichlorofluoromethane is a member of a class of molecules called chlorofluorocarbons or CFCs, which contain one or two carbon atoms and several halogens. Trichlorofluoromethane is an unusual organic molecule in that it contains no hydrogen atoms.

Because it has a low molecular weight and is easily vaporized, trichlorofluoromethane has been used as an aerosol propellant and refrigerant. It and other CFCs have been implicated in the destruction of the stratospheric ozone layer, a topic discussed in Chapter 15.

Three complex organic molecules that are important medications are amoxicillin, fluoxetine, and AZT. 

Amoxicillin is one of the most widely used antibiotics in the penicillin family.

The discovery and synthesis of such antibiotics in the twentieth century have made routine the treatment of infections that were formerly fatal. You were likely given some amoxicillin to treat an ear infection when you were a child. The penicillin antibiotics are discussed in Chapter 22.

Fluoxetine is the generic name for the antidepressant Prozac. Prozac was designed and synthesized by chemists in the laboratory, and is now produced on a large scale in chemical factories. Because it is safe and highly effective in treating depression, Prozac is widely prescribed. Over 40 million individuals worldwide have used Prozac since 1986.

AZT, azidodeoxythymidine, is a drug that treats the human immunodeficiency virus (HIV), the virus that causes acquired immune deficiency syndrome (AIDS). Also known by its generic name zidovudine, AZT represents a chemical success to a different challenge: synthesizing agents that combat viral infections.

Other complex organic compounds having interesting properties are capsaicin and DDT.

Capsaicin, one member of a group of compounds called vanilloids, is responsible for the characteristic spiciness of hot peppers.

It is the active ingredient in pepper sprays used for personal defense and topical creams used for pain relief.

DDT, dichlorodiphenyltrichloroethane, is a pesticide once called “miraculous” by Winston Churchill because of the many lives it saved by killing disease-carrying mosquitoes.

DDT use is now banned in the United States and many developed countries because it is a nonspecific insecticide that persists in the environment.

What are the common features of these organic compounds?

  • All organic compounds contain carbon atoms and most contain hydrogen atoms.
  • All the carbon atoms have four bonds. A stable carbon atom is said to be tetravalent.
  • Other elements may also be present. Any atom that is not carbon or hydrogen is called a heteroatom. Common heteroatoms include N, O, S, P, and the halogens.
  • Some compounds have chains of atoms and some compounds have rings.

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