organic chemistry assignment pdf

Organic Chemistry - A Tenth Edition

John E. McMurry, Cornell University

Copyright Year: 2023

ISBN 13: 9781951693985

Publisher: OpenStax

Language: English

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Reviewed by Mary Robert Garrett, Professor of Chemistry and Division I (BIO, CHM, MAT, NUR, PHY) Chair, Berea College on 11/29/23

Yes. This textbook covers a wealth of organic chemistry content and could be used for three organic chemistry courses--Organic Chemistry I, Organic Chemistry II, and Advanced Organic Chemistry. Key terms can be found bolded in the text, and in a... read more

Comprehensiveness rating: 5 see less

Yes. This textbook covers a wealth of organic chemistry content and could be used for three organic chemistry courses--Organic Chemistry I, Organic Chemistry II, and Advanced Organic Chemistry. Key terms can be found bolded in the text, and in a list at the end of each chapter with links to where they are used in the text. The Study Guide and Student Solutions manual are also openly licensed and free for students in digital formats.

Content Accuracy rating: 5

The content appears to be essentially error-free. There may be a missing chemical subscript missing in a place, or two, but nothing that will confuse a student or hinder their learning.

Relevance/Longevity rating: 5

The content is current with applications to everyday life at the end of each chapter in a section titled, “Chemistry Matters.” Examples range from the importance of Vitamin D, to how epoxy resins and adhesives are used in commercial products, to cocaine and anesthetics.

Clarity rating: 5

The text is very easy to follow with figures and tables well-placed. New terms are highlighted and strengthen content knowledge.

Consistency rating: 5

Yes, each chapter is displayed in the same format beginning with a "Why is this important" and ending with "Chemistry Matters." The subsections are consistent as well.

Modularity rating: 5

The textbook has excellent modularity. I see chapters that can be pulled for three different courses—Organic Chemistry I (Chapters 1-13); Organic Chemistry II (Chapters 14-24); and Advanced Organic Chemistry (Sections 5.9-5.12, Chapter 30, and 31), where students can read a later chapter and understand it at a particular level without rereading a previous chapter.

Organization/Structure/Flow rating: 5

The order of the content is different than the text I normally teach from, but the author does an excellent job of defending this specific order, so I think I’ll give it a try. I like the chapter on “An Overview of Organic Reactions” before diving into reaction classes. I think it will help students recognize the similarities and patterns between reactions. I normally teach the mass spec, NMR and IR chapters out of order, sooner than listed. The analysis of those instruments is so different, that students normally struggle with such a “different” concept at the end of a semester.

Interface rating: 4

One inconsistency that I found distracting was the size of the structures throughout the text. In one table, the chemical structures changed size from molecule to molecule which distracted from the flow. The interface was okay moving between the end-of-section practice problems and the solutions, but it gave away all of the answers with one click. I was also hoping for a bit of interaction with the 3D molecules. I was expecting to be able to manipulate them. While that certainly goes beyond what a typical textbook can do, that would certainly make the online textbook far more engaging.

Grammatical Errors rating: 5

I did not notice any.

Cultural Relevance rating: 2

I was pleased to see a linked resource by Dr. Rhett Smith (Clemson University) to provide a “more complete, diverse, and inclusive picture of the development and current state of organic chemistry research.” This component acknowledges the need for diversity. While there was a Japanese track team, a black music conductor (leading a white orchestra), and one sunbather of color, the majority of images were of white people (scientist on the computer (though female), pole vaulter, Kansas City pitcher, officer with a "drunkometer" test, kayaker, rock climber, officers with tear gas masks, etc.). I would have appreciated more diversity in the images.

I do really like the content, the level of explanation, the images, and clarity of this textbook. I plan to use it for my Organic Chemistry II course next spring, as well as my Advanced Organic Chemistry course.

Table of Contents

• Dedication and Preface
• Chapter 1: Structure and Bonding
• Chapter  2: Polar Covalent Bonds; Acids and Bases
• Chapter  3: Organic Compounds: Alkanes and Their Stereochemistry
• Chapter  4: Organic Compounds: Cycloalkanes and Their Stereochemistry
• Chapter  5: Stereochemistry at Tetrahedral Centers
• Chapter  6: An Overview of Organic Reactions
• Chapter  7: Alkenes: Structure and Reactivity
• Chapter  8: Alkenes: Reactions and Synthesis
• Chapter  9: Alkynes: An Introduction to Organic Synthesis
• Chapter  10: Organohalides
• Chapter  11: Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
• Chapter  12: Structure Determination: Mass Spectrometry and Infrared Spectroscopy
• Chapter  13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy
• Chapter  14: Conjugated Compounds and Ultraviolet Spectroscopy
• Chapter  15: Benzene and Aromaticity
• Chapter  16: Chemistry of Benzene: Electrophilic Aromatic Substitution
• Chapter  17: Alcohols and Phenols
• Chapter  18: Ethers and Epoxides; Thiols and Sulfides
• Chapter  19: Aldehydes and Ketones: Nucleophilic Addition Reactions
• Chapter  20: Carboxylic Acids and Nitriles
• Chapter  21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
• Chapter  22: Carbonyl Alpha-Substitution Reactions
• Chapter  23: Carbonyl Condensation Reactions
• Chapter  24: Amines and Heterocycles
• Chapter  25: Biomolecules: Carbohydrates
• Chapter  26: Biomolecules: Amino Acids, Peptides, and Proteins
• Chapter  27: Biomolecules: Lipids
• Chapter  28: Biomolecules: Nucleic Acids
• Chapter  29: The Organic Chemistry of Metabolic Pathways
• Chapter  30: Orbitals and Organic Chemistry: Pericyclic Reactions
• Chapter  31: Synthetic Polymers
• Appendix A. Nomenclature of Polyfunctional Organic Compounds
• Appendix B. Acidity Constants for Some Organic Compounds
• Appendix C. Glossary
• Appendix D. Periodic Table

Ancillary Material

About the book.

John McMurry's  Organic Chemistry  is renowned as the most clearly written book available for organic chemistry. In John McMurry's words, "I wrote this book because I love writing. I get great pleasure and satisfaction from taking a complicated subject, turning it around until I see it clearly from a new angle, and then explaining it in simple words." In  Organic Chemistry: A Tenth Edition  from OpenStax, McMurry continues this tradition while updating scientific discoveries, highlighting new applications, scrutinizing every piece of art, and providing example problems to assist students.  Organic Chemistry: A Tenth Edition  continues to meet the scope and sequence of a two-semester organic chemistry course that follows a functional group approach. A highlighted list of changes along with a detailed table of contents and ancillary descriptions can be found on the Instructor and Student resources sections of this page. John McMurry decided to publish  Organic Chemistry: A Tenth Edition  under an open license as a tribute to his son, Peter McMurry, who passed away from cystic fibrosis in December 2019. Please  click here  to learn more about Peter's legacy and to  support the fight against cystic fibrosis.

About the Contributors

John E. McMurry is a Professor Emeritus in the Department of Chemistry and Chemical Biology at Cornell University. He holds an A.B. degree from Harvard University and a Ph.D. from Columbia University. McMurry has authored over 100 research papers and is well-known for his contributions to the field of chemistry, particularly the development of the McMurry reaction. This reaction involves the coupling of two molecules of ketone or aldehyde to produce an alkene when treated with titanium(III) chloride and a reducing agent like Zn(Cu). The McMurry reaction has found extensive use in the laboratory synthesis of complex organic molecules and in the commercial synthesis of various drugs by the pharmaceutical industry.

McMurry was elected a Fellow of the American Association for the Advancement of Science in 1985 and received a Max Planck Society Research Award in 1991. Apart from his scientific contributions, McMurry is also a prolific author in the field of chemistry education. He has written 45 undergraduate chemistry textbooks, which have been translated into 12 languages and used worldwide. Among his notable works,  Organic Chemistry , first published in 1984, stands as his most popular textbook.

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1.1: Introduction to organic chemistry

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1.1. Introduction to organic chemistry

Learning objectives.

• Define organic chemistry .
• Identify organic molecules as alkanes, alkenes, alkynes, alcohols, or carboxylic acids.

Organic chemistry is the study of the chemistry of carbon compounds. Carbon is singled out because it has a chemical diversity unrivaled by any other chemical element. Its diversity is based on the following:

• Carbon atoms bond reasonably strongly with other carbon atoms.
• Carbon atoms bond reasonably strongly with atoms of other elements.
• Carbon atoms make a large number of covalent bonds (four).

Curiously, elemental carbon is not particularly abundant. It does not even appear in the list of the most common elements in Earth’s crust .  Nevertheless, all living things consist of organic compounds.

Most organic chemicals are covalent compounds, which is why we introduce organic chemistry here. By convention, compounds containing carbonate ions and bicarbonate ions, as well as carbon dioxide and carbon monoxide, are not considered part of organic chemistry, even though they contain carbon.

The simplest organic compounds are the hydrocarbons , compounds composed of carbon and hydrogen atoms only. Some hydrocarbons have only single bonds and appear as a chain (which can be a straight chain or can have branches) of carbon atoms also bonded to hydrogen atoms. These hydrocarbons are called alkanes (saturated hydrocarbons) . Each alkane has a characteristic, systematic name depending on the number of carbon atoms in the molecule. These names consist of a stem that indicates the number of carbon atoms in the chain plus the ending – ane . The stem meth – means one carbon atom, so methane is an alkane with one carbon atom. Similarly, the stem eth – means two carbon atoms; ethane is an alkane with two carbon atoms. Continuing, the stem prop – means three carbon atoms, so propane is an alkane with three carbon atoms. Figure 1.1. “Formulas and Molecular Models of the Three Simplest Alkanes” gives the formulas and the molecular models of the three simplest alkanes. (For more information about alkanes, see section 3.3. )

Figure 1.1. Formulae and molecular models of the three simplest alkanes

The three smallest alkanes are methane, ethane, and propane.

Some hydrocarbons have one or more carbon–carbon double bonds (denoted C=C). These hydrocarbons are called alkenes (see section 3.2. for more information) Note that the names of alkenes have the same stem as the alkane with the same number of carbon atoms in its chain but have the ending – ene . Thus, ethene is an alkene with two carbon atoms per molecule, and propene is a compound with three carbon atoms and one double bond.

Figure 1.2. Formulas and Molecular Models of the Two Simplest Alkenes

Ethene is commonly called ethylene, while propene is commonly called propylene.

Alkynes are hydrocarbons with a carbon–carbon triple bond (denoted C≡C) as part of their carbon skeleton (see section 3.2. for more information). The names for alkynes have the same stems as for alkanes but with the ending – yne .

Figure 1.3. Formulas and Molecular Models of the Two Simplest Alkynes

Ethyne is more commonly called acetylene.

To your health: saturated and unsaturated fats

Hydrocarbons are not the only compounds that can have carbon–carbon double bonds. A group of compounds called fats can have them as well, and their presence or absence in the human diet is becoming increasingly correlated with health issues.

Fats are combinations of long-chain organic compounds (fatty acids) and glycerol (C 3 H 8 O 3 ). The long carbon chains can have either all single bonds, in which case the fat is classified as saturated , or one or more double bonds, in which case it is a monounsaturated or a polyunsaturated fat, respectively. Saturated fats are typically solids at room temperature; beef fat (tallow) is one example. Mono- or polyunsaturated fats are likely to be liquids at room temperature and are often called oils. Olive oil, flaxseed oil, and many fish oils are mono- or polyunsaturated fats.

Some studies have linked higher amounts of saturated fats in people’s diets with a greater likelihood of developing heart disease, high cholesterol, and other diet-related diseases. In contrast, increases in unsaturated fats (either mono- or polyunsaturated) have been linked to a lower incidence of certain diseases. Thus, there have been recommendations by government bodies and health associations to decrease the proportion of saturated fat and increase the proportion of unsaturated fat in the diet. Most of these organizations also recommend decreasing the total amount of fat in the diet.  A difference as simple as the difference between a single and double carbon–carbon bond can have a significant impact on health.

The carbon–carbon double and triple bonds are examples of functional groups in organic chemistry. A functional group is a specific structural arrangement of atoms or bonds that imparts a characteristic chemical reactivity to a molecule. Alkanes have no functional group, and they are mostly inert (unreactive). A carbon–carbon double bond is considered a functional group because carbon–carbon double bonds chemically react in specific ways that differ from reactions of alkanes (for example, under certain circumstances, alkenes react with water); a carbon–carbon triple bond also undergoes certain specific chemical reactions. In the remainder of this section, we introduce two other common functional groups.

If an OH group (also called a hydroxyl group) is substituted for a hydrogen atom in a hydrocarbon molecule, the compound is an alcohol . Alcohols are named using the parent hydrocarbon name but with the final – e dropped and the suffix – ol attached. The two simplest alcohols are methanol and ethanol (see Figure 1.4.).

Figure 1.4. The two simplest organic alcohol compounds

Alcohols have an OH functional group in the molecule.  Ethanol (also called ethyl alcohol) is the alcohol in alcoholic beverages. Other alcohols include methanol (or methyl alcohol), which is used as a solvent and a cleaner, and 2-propanol (also called isopropyl alcohol or rubbing alcohol), which is used as a medicinal disinfectant. Neither methanol nor isopropyl alcohol should be ingested, as they are toxic even in small quantities.  Cholesterol is an example of a more complex alcohol.

Another important family of organic compounds has a carboxyl group , in which a carbon atom is double-bonded to an oxygen atom and to an OH group. Compounds with a carboxyl functional group are called carboxylic acids , and their names end in – oic acid . The two simplest carboxylic acids are shown in Figure 1.5.  They are perhaps best known by the common names formic acid (found in the stingers of ants) and acetic acid (found in vinegar).  The carboxyl group is sometimes written in molecules as COOH.

Figure 1.5. The two smallest organic acids

Many organic compounds are considerably more complex than the examples described here. Many compounds contain more than one functional group. The formal names can also be quite complex. In section 1.6. we will examine functional groups in more detail, and we will learn about the system of naming (nomenclature) for hydrocarbons in chapter 3 .

Identify the functional group(s) in each molecule as a double bond, a triple bond, an alcohol, or a carboxyl.

• CH 3 CH 2 CH 2 CH 2 OH

• This molecule has an alcohol functional group.
• This molecule has a double bond and a carboxyl functional group.

Skill-building exercise

Concept review exercises

What is organic chemistry?

What is a functional group? Give at least two examples of functional groups.

• Organic chemistry is the study of the chemistry of carbon compounds.

A functional group is a specific structural arrangement of atoms or bonds that imparts a characteristic chemical reactivity to the molecule; alcohol group and carboxylic group (answers will vary).

Key takeaways

• Organic molecules can be classified according to the types of elements and bonds in the molecules.

Give three reasons why carbon is the central element in organic chemistry.

Are organic compounds based more on ionic bonding or covalent bonding? Explain.

Identify the type of hydrocarbon in each structure.

Identify the functional group(s) in each molecule.

How many functional groups described in this section contain carbon and hydrogen atoms only? Name them.

What is the difference in the ways the two oxygen atoms in the carboxyl group are bonded to the carbon atom?

Carbon atoms bond reasonably strongly with other carbon atoms. Carbon atoms bond reasonably strongly with atoms of other elements. Carbon atoms make a large number of covalent bonds (four).

• carbon-carbon double bond and carbon-carbon triple bond

two; carbon-carbon double bonds and carbon-carbon triple bonds

Further reading

• Communicating chemical structure with formulas and names

• Authored by : Saylor Academy. License : CC BY-NC-SA: Attribution-NonCommercial-ShareAlike

Module 20: Organic Chemistry

Assignment: organic chemistry practice.

• Write the chemical formula, and Lewis structure for each of the following hydrocarbons:

(a) pentane

(b) 3-ethylhexane

(c) cis-4-hepten-1-ol

(d) 4-methyl-1-hexene

(e) 2-heptyne

(f) 3,4-dimethyl-1-octyne

• Describe the difference between a saturated and unsaturated hydrocarbon. What would the hybridization be at the crucial carbons in each kind of molecule?
• Write a condensed structural formula, such as CH3CH3, and describe the molecular geometry at each carbon atom.

(a) propene

(b) 1-butanol

(c) ethyl propyl ether

(d) cis-4-bromo-2-heptene

(e) 2,2,3-trimethylhexane

(f) formaldehyde

• Write out the resonance structures for the acetate ion.
• Complete the activity linked here ( https://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/questions/General/match10.htm ) doing structure matching to formulas. Come back and type the letter answers in the order they appeared (Left to right).
• Complete the activity linked here . ( https://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/questions/General/match2.htm ). This activity challenges your ability to recognize organic figures that might be the same. Write something here certifying that you completed this learning activity.

Browse Course Material

Course info, instructors.

• Dr. Sarah Tabacco
• Prof. Barbara Imperiali

Departments

As taught in.

• Organic Chemistry

Learning Resource Types

Organic chemistry i, assignments.

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Organic chemistry

A brief introduction to organic chemistry, unit 1: structure and bonding, unit 2: resonance and acid-base chemistry, unit 3: alkanes, cycloalkanes, and functional groups, unit 4: stereochemistry, unit 5: substitution and elimination reactions, unit 6: alkenes and alkynes, unit 7: alcohols, ethers, epoxides, sulfides, unit 8: conjugated systems and pericyclic reactions, unit 9: aromatic compounds, unit 10: aldehydes and ketones, unit 11: carboxylic acids and derivatives, unit 12: alpha carbon chemistry, unit 13: amines, unit 14: spectroscopy.

CHEM0350 Organic Chemistry Lab

• Finding Chemical Information

Learning Goals

Tips for success: using reaxys and primary literature.

• Citing the Literature
• Experiment #4
• Troubleshooting Electronic Resources

This assignment is meant to teach you how to use certain chemistry resources. As the lecture could not cover all the features of each resource, it is expected that students will explore these resources through the assignment. 

Upon completion of this assignment, students should be able to:

• Recognize that a chemist finds property data in the literature to validate conclusions based on property data measured experimentally, especially for synthesis of substances.
• Find property data in online handbooks (tertiary sources).
• Find property data in a scholarly research article database and the associated article (primary source).
• Cite resources using a CHEM0350 citation style guide.

Choosing an Article

For this assignment, select the reference with the most current year of publication that has the property data that you need, measured under the given experimental conditions, and is available (full text) through our library.

If the pressure entry for boiling point is blank in a Reaxys property table, then the experimental condition is atmospheric pressure.

A Reaxys table may have a solvent column associated with melting point data. The article used for this assignment should not have a solvent listed in the table entry.

In addition, the location entry of the table should be empty.  This indicates that the data is found in the journal article.  Do not use an article with the location specified as "Supporting Information".

Accessing the Full Text of an Article

Be sure to note the DOI of the article, which is available in one or more of the following places: the Interlibrary Loan page; the journal's page for the article, below the title and authors or in an 'About this Article' section; the PDF of the article.

Finding Property Data in an Article

Be aware that authors can use condensed structures of functional groups. See your lecture text for examples.

In organic chemistry research articles, data can be found in tables, figures, or text.  If several compounds are being studied, the author(s) often assigns a structure number to keep track of the compounds. This number can be a letter, number, or letter/number combination.  To find the structure number, look for the first mention of your substance in the text, figures, or tables.

It is possible that the property data for a substance is reported in an article not about synthesizing the substance but to validate that the substance, as a reactant, is as pure as possible.

Citing your Sources

It is not uncommon that original research papers reference their obtained experimental findings to a literature value (lit.) from an earlier published paper.  The paper you utilize is the one that should be cited.

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• Next: Citing the Literature >>
• Last Updated: Feb 19, 2023 3:46 AM
• URL: https://libguides.brown.edu/CHEM0350L

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