Different styles of drawing a methyl group (highlighted in blue)

Methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms —CH₃. The group is often abbreviated Me. Such hydrocarbon groups occur in many organic compounds. The methyl group can be found in three forms: anion, cation and radical. The anion has eight valence electrons, the radical seven and the cation six. All three are highly reactive and rarely observed.^[1]

Methyl cation, anion, and radical[link]

Methyl cation[link]

The methylium cation (CH₃⁺) exists in the gas phase, but is otherwise not encountered. Some compounds, are considered to be sources of "CH₃⁺," and this simplification is used pervasively in organic chemistry. For example, protonation of methanol gives a strongly electrophilic methylating reagent:

CH₃OH + H⁺ → CH₃⁺ + H₂O

Similarly, methyl iodide and methyl triflate are viewed as the equivalent of the methyl cation because they readily undergo S_N2 reactions by weak nucleophiles.

Methyl anion[link]

The methanide anion (CH₃^-) similarly exists only under exotic conditions. In discussing mechanisms of organic reactions, it is often a useful simplification to consider methyl lithium and related Grignard reagents as sal sources of "CH₃^-," although this view is fiction. Such reagents are generally prepared from the methyl halides:

M + CH₃X → MCH₃

where M is alkali metal.

Methyl radical[link]

The methyl radical has the formula CH₃. It exists in dilute gases, but in more concentrated form it readily dimerizes to ethane. It can be produced by thermal decomposition of only certain compounds, especially those with an -N=N- linkage.

Reactivity[link]

The reactivity of a methyl group depends on the adjacent substituents. Methyl groups can be quite unreactive. For example, in organic compounds, the methyl group resists attack by even the strongest acids.

Oxidation[link]

The oxidation of a methyl group occurs widely in nature and industry. The oxidation products derived from methyl are CH₂OH, CHO, and CO₂H. For example, permanganate often converts a methyl group to a carboxyl (-COOH) group, e.g. the conversion of toluene to benzoic acid. Ultimately oxidation of methyl groups gives protons and carbon dioxide, as seen in combustion.

Methylation[link]

Demethylation (the transfer of the methyl group to another compound) is a common process, and reagents that undergo this reaction are called methylating agents. Common methylating agents are dimethylsulfate, methyl iodide, and methyl triflate. Methanogenesis, the source of natural gas, arises via a demethylation reaction.^[2]

Deprotonation[link]

Certain methyl groups can be deprotonated. For example, the acidity of the methyl groups in acetone ((CH₃)₂CO) is about 10²⁰ more acidic than methane. The resulting carbanions are key intermediates in many reactions in organic synthesis and biosynthesis. Fatty acids arise in this way.

Free radical reactions[link]

When placed in benzylic or allylic positions, the C-H bond strength is decreased, and the reactivity of the methyl group increases. One manifestation of this enhanced reactivity is the photochemical chlorination of the methyl group in toluene to give benzyl chloride.^[3]

Etymology[link]

French chemists Jean-Baptiste Dumas and Eugene Peligot, after determining methanol's chemical structure, introduced "methylene" from the Greek methy = "wine" + hȳlē = "wood" (patch of trees) with the intention of highlighting its origins, "alcohol made from wood (substance)", but with Greek language errors: the Greek for "wood (substance)" is xylo-. The term "methyl" was derived in about 1840 by back-formation from "methylene", and was then applied to describe "methyl alcohol".

Methyl is the IUPAC nomenclature of organic chemistry term for an alkane (or alkyl) molecule, using the prefix "meth-" to indicate the presence of a single carbon.

See also[link]

• Methanol
• Methane

References[link]

1. ^ March, J. Advanced Organic Chemistry. 4th Ed. J. Wiley and Sons, 1992: New York. ISBN 0-471-60180-2.
2. ^ Thauer, R. K., "Biochemistry of Methanogenesis: a Tribute to Marjory Stephenson", Microbiology, 1998, volume 144, pages 2377–2406.
3. ^ M. Rossberg et al. “Chlorinated Hydrocarbons” in Ullmann’s Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a06_233.pub2

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Dave Palumbo flexing in photo shoot.

Dave Palumbo (born David Christopher Palumbo February 17, 1968 in Manhattan, U.S.) is an American bodybuilder.^[1] He competed in his first Bodybuilding competition in 1990, an NPC national competition in New York City where he placed 6th place weighing in at 168 lbs.^[2] He continues to compete with his highest placing being that of 2nd place in 2003 in the 'Super Heavyweight' class at the NPC USA competition in Las Vegas, Nevada.

He operates a bodybuilding magazine website, rxmuscle.com, which examines all aspects of training, competing, and nutrition as well as radio and TV programming. ^[3] He is also the owner of Species Nutrition.^[4]

Competitive history[link]

1990 NPC NATURAL New York City (6th place Middleweight.....168 lbs)..training only 6 months

1992 NPC NJ SUBURBAN BODYBUILDING CHAMPS (5th place, Light HW.....198 lbs)

1992 NATURAL TRI STATE CHAMPIONSHIPS (1st place, Heavyweight........202 lbs)

1992 NPC Eastern USA 3rd place HW...212 lbs

1992 NPC WESTCHESTER 2nd place HW ...212 lbs

1994 NPC NY METROPOLITAN BB CHAMPS 1st HW.......228 lbs

1994 NPC SUBURBAN BB CHAMPS 2nd HW........228 lbs

1994 NPC Jr USA 3rd place HW...........228 lbs

1994 AMATEUR GRAND PRIX 1st place HW and OVERALL CHAMP......235 lbs

1995 NPC Jr NATIONALS 1st place HW........258 lbs

1995 NPC USA CHAMPS 7th place HW.........256 lbs

1996 NPC USA 7th place.........254 lbs

1996 NPC NATIONALS 4th place.........268 lbs

1997 NPC USA 6th place .....270 lbs

1997 NPC NATIONALS.....5th place........272 lbs

1998 IFBB NORTH AMERICAN 6th place .......281 lbs

1998 NPC NATIONALS 8th place Super HW....... 273 lbs

1999 NPC USA ......9th place

2000 NPC NY METROPOLITAN 1st place Super HW and OVERALL.... 275 lbs

2000 NPC USA 4th place Super HW.......274 lbs

2000 NPC NATIONALS 8th place Super HW......268 lbs

2001 NPC USA 7th place .......Super HW....... 265 lbs

2001 IFBB NORTH AMERICAN 5th place...... Super HW ...... 271 lbs

2002 NPC USA 3rd place Super HW...........260 lbs

2002 NPC National's 2nd place Super HW.......260 lbs

2003 NPC USAs 2nd place Super HW...........265 lbs

2003 NPC NATIONALS 6th place Super HW.......268 lbs

2004 NPC USA 6th place Super HW....... 258 lbs

References[link]

1. ^ Dan Barry (December 21, 1996). "The Hidden Aspects Of Showy Muscles; Despite the Dangers of Steroids, Bodybuilders Are Still Tempted". The New York Times. 
2. ^ Aaron Wilkinson (June 27, 2002). "Bodybuilding show attracts young and old; Promoter highlights roots of sport in N.O.". Times-Picayune. 
3. ^ Daryn Kagan, Dr. Sanjay Gupta (June 3, 2003). "AIDS Drug Entering Black Market". American Morning. 060302CN.V74. CNN. 
4. ^ "Get Pump With Ian-Palumbo Diet". Real Muscle Online. December 4, 2008. 

Jim Cochran is a pioneering organic strawberry farmer, who was the first person to grow strawberries organically on a commercial scale in California.^[1] Cochran was born in Carlsbad, California in 1947. He studied child development and European intellectual history at the University of California, Santa Cruz in the late 1960s, where he became interested in alternative farming methods.^[2] Cochran began his commercial farming career growing strawberries using conventional methods, but switched to organic methods after he was nearly poisoned by pesticides and, as a result of this experience, questioned the effect that the chemicals had on his workers.^[1] He started Swanton Berry Farm in 1983 near Santa Cruz, California and subsequently developed a wide range of new methods, which include crop rotations, such as broccoli and brussels sprouts, trap crops such as mustard and alfalfa, and the use of natural predators, to control strawberry specific pests and diseases.^[3] His mostly intuitively developed methods were later verified scientifically in a series of studies by University of California, Davis plant pathologist Krishna Subbarao and his collaborators.^[4] Cochran originally found it difficult to get funding for his experiments from the California Strawberry Commission, stating that "The industry blockaded our efforts to get money to research alternatives, and spent a lot of money in Washington making sure our proposals didn't get funded."^[1] Cochran's methods have been credited for making a large-scale commercial organic strawberry industry possible in California.^[3] Cochran was also the first, and still one of the few, California organic farmers to have a contract with the United Farm Workers.^[2][3]

References[link]

Further reading[link]

• University of California, Santa Cruz oral history interview with Cochran