John E. McMurry

Last updated
John McMurry
Born (1942-07-27) July 27, 1942 (age 81)
Alma mater Harvard University A.B. 1964
Columbia University Ph.D. 1967
Known for McMurry reaction
Scientific career
Institutions University of California, Santa Cruz,
Cornell University
Doctoral advisor Gilbert Stork

John E. McMurry (born July 27, 1942, in New York City) is Professor Emeritus in the Department of Chemistry and Chemical Biology at Cornell University. He received an A.B. from Harvard University in 1964 and his Ph.D. from Columbia University in 1967 working with Gilbert Stork. Following completion of his Ph.D., he joined the faculty of the University of California, Santa Cruz in 1967 and moved to Cornell University in 1980.

Contributions

The author of more than 100 research papers, McMurry is best known scientifically for his development of the McMurry reaction, in which two molecules of ketone or aldehyde are coupled to give an alkene when treated with titanium(III) chloride and a reducing agent such as Zn(Cu). [1] The reaction has been widely used by the chemical community in the laboratory synthesis of many complex organic molecules and by the pharmaceutical industry in the commercial synthesis of several drugs.[ citation needed ] 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. [2]

In addition to his scientific work, McMurry is the author of 45 undergraduate chemistry textbooks that have been translated into 12 languages and used throughout the world. McMurry's most popular textbook Organic Chemistry was first printed in 1984. In 2022, he sold the rights for the book to OpenStax making it free for the user. [3] [4] Among his other texts are:

Related Research Articles

<span class="mw-page-title-main">Inorganic chemistry</span> Field of chemistry

Inorganic chemistry deals with synthesis and behavior of inorganic and organometallic compounds. This field covers chemical compounds that are not carbon-based, which are the subjects of organic chemistry. The distinction between the two disciplines is far from absolute, as there is much overlap in the subdiscipline of organometallic chemistry. It has applications in every aspect of the chemical industry, including catalysis, materials science, pigments, surfactants, coatings, medications, fuels, and agriculture.

<span class="mw-page-title-main">Organic chemistry</span> Subdiscipline of chemistry, focusing on carbon compounds

Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms. Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical study.

The following outline is provided as an overview of and topical guide to organic chemistry:

<span class="mw-page-title-main">Aldol reaction</span> Chemical reaction

The aldol reaction is a reaction in organic chemistry that combines two carbonyl compounds to form a new β-hydroxy carbonyl compound. Its simplest form might involve the nucleophilic addition of an enolized ketone to another:

<span class="mw-page-title-main">Lithium aluminium hydride</span> Chemical compound

Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula Li[AlH4] or LiAlH4. It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters, carboxylic acids, and amides. The solid is dangerously reactive toward water, releasing gaseous hydrogen (H2). Some related derivatives have been discussed for hydrogen storage.

<span class="mw-page-title-main">Zinc chloride</span> Chemical compound

Zinc chloride is an inorganic chemical compound with the formula ZnCl2·nH2O, with n ranging from 0 to 4.5, forming hydrates. Zinc chloride, anhydrous and its hydrates, are colorless or white crystalline solids, and are highly soluble in water. Five hydrates of zinc chloride are known, as well as four forms of anhydrous zinc chloride. All forms of zinc chloride are deliquescent. Zinc chloride finds wide application in textile processing, metallurgical fluxes, and chemical synthesis. In a major monograph, zinc chlorides have been described as "one of the important compounds of zinc."

<span class="mw-page-title-main">Allyl group</span> Chemical group (–CH₂–CH=CH₂)

In organic chemistry, an allyl group is a substituent with the structural formula −CH2−HC=CH2. It consists of a methylene bridge attached to a vinyl group. The name is derived from the scientific name for garlic, Allium sativum. In 1844, Theodor Wertheim isolated an allyl derivative from garlic oil and named it "Schwefelallyl". The term allyl applies to many compounds related to H2C=CH−CH2, some of which are of practical or of everyday importance, for example, allyl chloride.

<span class="mw-page-title-main">Titanium tetrachloride</span> Inorganic chemical compound

Titanium tetrachloride is the inorganic compound with the formula TiCl4. It is an important intermediate in the production of titanium metal and the pigment titanium dioxide. TiCl4 is a volatile liquid. Upon contact with humid air, it forms thick clouds of titanium dioxide and hydrochloric acid, a reaction that was formerly exploited for use in smoke machines. It is sometimes referred to as "tickle" or "tickle 4", as a phonetic representation of the symbols of its molecular formula.

The Reformatsky reaction is an organic reaction which condenses aldehydes or ketones with α-halo esters using metallic zinc to form β-hydroxy-esters:

The Wöhler synthesis is the conversion of ammonium cyanate into urea. This chemical reaction was described in 1828 by Friedrich Wöhler. It is often cited as the starting point of modern organic chemistry. Although the Wöhler reaction concerns the conversion of ammonium cyanate, this salt appears only as an (unstable) intermediate. Wöhler demonstrated the reaction in his original publication with different sets of reactants: a combination of cyanic acid and ammonia, a combination of silver cyanate and ammonium chloride, a combination of lead cyanate and ammonia and finally from a combination of mercury cyanate and cyanatic ammonia.

A pinacol coupling reaction is an organic reaction in which a carbon–carbon bond is formed between the carbonyl groups of an aldehyde or a ketone in presence of an electron donor in a free radical process. The reaction product is a vicinal diol. The reaction is named after pinacol, which is the product of this reaction when done with acetone as reagent. The reaction is usually a homocoupling but intramolecular cross-coupling reactions are also possible. Pinacol was discovered by Wilhelm Rudolph Fittig in 1859.

<span class="mw-page-title-main">McMurry reaction</span>

The McMurry reaction is an organic reaction in which two ketone or aldehyde groups are coupled to form an alkene using a titanium chloride compound such as titanium(III) chloride and a reducing agent. The reaction is named after its co-discoverer, John E. McMurry. The McMurry reaction originally involved the use of a mixture TiCl3 and LiAlH4, which produces the active reagents. Related species have been developed involving the combination of TiCl3 or TiCl4 with various other reducing agents, including potassium, zinc, and magnesium. This reaction is related to the Pinacol coupling reaction which also proceeds by reductive coupling of carbonyl compounds.

Titanium(III) chloride is the inorganic compound with the formula TiCl3. At least four distinct species have this formula; additionally hydrated derivatives are known. TiCl3 is one of the most common halides of titanium and is an important catalyst for the manufacture of polyolefins.

<span class="mw-page-title-main">Organotitanium chemistry</span>

Organotitanium chemistry is the science of organotitanium compounds describing their physical properties, synthesis, and reactions. Organotitanium compounds in organometallic chemistry contain carbon-titanium chemical bonds. They are reagents in organic chemistry and are involved in major industrial processes.

In organic chemistry, the Nef reaction is an organic reaction describing the acid hydrolysis of a salt of a primary or secondary nitroalkane to an aldehyde or a ketone and nitrous oxide. The reaction has been the subject of several literature reviews.

The Barton reaction, also known as the Barton nitrite ester reaction, is a photochemical reaction that involves the photolysis of an alkyl nitrite to form a δ-nitroso alcohol.

An insertion reaction is a chemical reaction where one chemical entity interposes itself into an existing bond of typically a second chemical entity e.g.:

<span class="mw-page-title-main">Bis(cyclopentadienyl)titanium(III) chloride</span> Chemical compound

Bis(cyclopentadienyl)titanium(III) chloride, also known as the Nugent–RajanBabu reagent, is the organotitanium compound which exists as a dimer with the formula [(C5H5)2TiCl]2. It is an air sensitive green solid. The complex finds specialized use in synthetic organic chemistry as a single electron reductant.

Thomas Lectka is an American organic chemist, academic and researcher. He is Jean and Norman Scowe Professor of Chemistry and leads the Lectka Group at Johns Hopkins University.

<span class="mw-page-title-main">Teruaki Mukaiyama</span> Japanese chemist (1927–2018)

Teruaki Mukaiyama was a Japanese organic chemist. One of the most prolific chemists of the 20th century in the field of organic synthesis, Mukaiyama helped establish the field of organic chemistry in Japan after World War II.

References

  1. Richards, Ian C. (2001). "Titanium(IV) Chloride-Zinc". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt125. ISBN   0471936235.
  2. McMurry, John (9 January 2024). "Organic Chemistry: Dedication and Preface". OpenStax.org. Houston, Texas. Retrieved 23 June 2024.
  3. Knox, Liam (August 11, 2022). "Popular chemistry textbook's new edition will be free". Inside Higher Ed . Retrieved 13 August 2022.
  4. Chawla, Dalmeet Singh (23 August 2022). "Best-selling organic chemistry textbook becomes open access". Chemistry World . Retrieved 23 June 2024.
  5. McMurry, J. E. (2015). ISBN   9781285842912
  6. McMurry, J. E., Fay, R. C., Robinson, J. K. (2019). ISBN   9780321943170
  7. McMurry, J. E., Fay, R. C. (2014). ISBN   9780321809261
  8. McMurry, J. E., Ballantine, D. S., Hoeger, C.A., Peterson, V. E. (2017). ISBN   9780134015187
  9. McMurry, J. E., Begley, T. P. (2016). ISBN   9781936221561