The structure of a benzyl cation

In organic chemistry, benzyl is the term used to describe the substituent or molecular fragment possessing the structure C₆H₅CH₂-. Organic chemistry is a discipline within Chemistry which involves the scientific study of the structure properties composition reactions, and preparation In Organic chemistry, a substituent is an atom or group of atoms substituted in place of a Hydrogen atom on the Parent chain of a Hydrocarbon The abbreviation "Bn" is frequently used to denote benzyl moieties in nomenclature and structural depictions of chemical compounds. For example, benzyl alcohol can be represented as BnOH. Benzyl alcohol is an Organic compound with the formula C6H5CH2OH This abbreviation is not to be confused with "Bz", which is the abbreviation for the benzoyl group C₆H₅C(O)-. In Organic chemistry, benzoyl is the Acyl of Benzoic acid, with structure C6H5CO-

The term benzyl is also used in reference to the carbocation^[1], anion, and free radical^[2] moieties featuring a benzene ring attached to a CH₂ group, in which the CH₂ group bears a positive charge, a negative charge, or a single unpaired electron respectively. A carbocation (ˌkɑrboʊˈkætaɪɒn is an Ion with a positively-charged Carbon Atom. An ion is an Atom or Molecule which has lost or gained one or more Valence electrons giving it a positive or negative electrical charge In Chemistry, radicals (often referred to as free radicals) are atoms molecules or ions with Unpaired electrons on an otherwise Open shell Benzene, or benzol, is an organic Chemical compound and a known Carcinogen with the molecular formula C 6 H 6

In substituent nomenclature, benzyl and phenyl are commonly confused. In Organic chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the Functional group with the formula - Benzyl can be seen as a phenyl attached to a CH₂ before attaching to the parent compound. In Organic chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the Functional group with the formula -

Benzyl protective groups

Benzyl groups are frequently used in organic synthesis as protective group for alcohols and carboxylic acids. Organic synthesis is a special branch of Chemical synthesis and is concerned with the construction of Organic compounds via Organic reactions Organic A protecting group or protective group is introduced into a molecule by chemical modification of a Functional group in order to obtain Chemoselectivity In Chemistry, an alcohol is any Organic compound in which a Hydroxyl group ( - O[[hydrogen H]]) is bound to a Carbon Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H

Two common methods for benzyl ether protection:

• reaction of alcohol with benzyl bromide and a strong base such as sodium hydride as in a Williamson ether synthesis^[3]
• reaction of alcohol with an imidate such as benzyl trichloroacetimidate (C₆H₅CH₂OC(CCl₃)=NH) promoted by trifluoromethanesulfonic acid. Sodium hydride is the Chemical compound with the formula NaH It is primarily used as a strong base in Organic synthesis. The Williamson ether synthesis was developed by Alexander Williamson in 1850. An imine is a Functional group or Chemical compound containing a Carbon – Nitrogen Double bond. Trifluoromethanesulfonic acid, also known as triflic acid or TfOH, is a Sulfonic acid with the chemical formula CF3SO3H. An example forming a p-methoxybenzyl (PMB) ether in total synthesis ^[4]:

The benzyl group can be removed by hydrogenation. Hydrogenation is the Chemical reaction that results in addition of Hydrogen (H2 PMB ethers can be cleaved by magnesium bromide –dimethyl sulfide, CAN or DDQ ^[5]. Magnesium bromide (MgBr2 is a Chemical compound of Magnesium and Bromine that is white and Deliquescent. Dimethyl sulfide (DMS or methylthiomethane is an organosulfur compound with the formula (CH32S Ceric ammonium nitrate, or in lab jargon "CAN" is the Chemical compound with the formula ( NH4)2Ce(NO36 "DDQ" redirects here DDQ is also the former callsign of a TV station in Toowoomba Queensland Australia

One study ^[6] employs a benzyl pyridinium salt as a benzyl donor for alcohols:

The solvent is trifluoromethylbenzene and magnesium oxide is an acid scavenger. Pyridine is a Chemical compound with the formula C5[[Hydrogen H5]] N. Magnesium oxide, or magnesia, is a white solid Mineral that occurs naturally as Periclase and is a source The reaction type for this conversion is believed to be SN1 based on the detection of trace amounts of Friedel-Crafts reaction sideproducts with toluene as a solvent. The SN1 reaction is a Substitution reaction in Organic chemistry. The Friedel-Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877. Toluene, also known as methylbenzene or phenylmethane, is a clear water -insoluble liquid with the typical smell of Paint thinners redolent of

References

1. ^ Carey, F. A. , and Sundberg, R. J. ; Advanced Organic Chemistry, Part A: Structure and Mechanisms, 5th ed. ; Springer: New York, NY, 2008. pp 806-808.
2. ^ Carey, F. A. , and Sundberg, R. J. ; Advanced Organic Chemistry, Part A: Structure and Mechanisms, 5th ed. ; Springer: New York, NY, 2008. pp 312-313.
3. ^ DeSelms, R. H. ; Benzyl Phenyl Ether Compounds; Enigen Science Publishing: Washington, DC, 2008.
4. ^ Total synthesis of rutamycin B via Suzuki macrocyclization James D. White, Thomas Tiller, Yoshihiro Ohba, Warren J. Porter, Randy W. Jackson, Shan Wang, and Roger Hanselmann 80 Chem. Commun., 1998 doi:10.1039/a707251a
5. ^ Protecting groups Krzysztof Jarowicki and Philip Kocienski J. Chem. Soc., Perkin Trans. Chemical Communications, known as ChemComm, is a peer-reviewed Scientific journal. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. The Journal of the Chemical Society was a Scientific journal published from 1862 to 1877 and from 1926 to 1965 by the Chemical Society which merged with other 1, 1998, 4005–4037 4005 doi:10.1039/a803688h
6. ^ K. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. W. C. Poon and G. B. Dudley (2006). "Mix-and-Heat Benzylation of Alcohols Using a Bench-Stable Pyridinium Salt". J. Org. Chem. 71 (10): 3923-3927. The Journal of Organic Chemistry (abbreviated as J Org Chem or JOC) is a Scientific journal for original contributions of fundamental doi:10.1021/jo0602773. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.