January 27, 2021

benzyl group vs phenyl group

Figure 2 shows the molecules benzyl chloride and phenyl chloride; these are based on the groups discussed above. • In phenyl, the benzene ring is directly attached to a substituent molecule or an atom, but in benzyl, the CH 2 group makes the connection with another molecule or an atom. For example, in nucleophilic substitution reactions, benzylic radical or cation intermediate is formed. Benzyl: The energy, necessary for the dissociation of the benzyl C-H bond is 90 kcal/mol. Forest Research Institute, Bulgarian Academy of Sciences. All rights reserved. The energy, necessary for the dissociation of the benzyl C-H bond is 90 kcal/mol. Consequently, when this aromatic ring was attached to something, it was called the "phenyl" group. The one thing to remember is, "when the benzene ring is attached to something, that is a phenyl group." Phenyl group alone is not stable because the carbon atom has an incomplete electron configuration due to the lack of a hydrogen atom to share an electron. As nouns the difference between phenyl and benzo Another molecular part (R group as depicted in the picture) can be attached to the benzyl group via bonding to the CH2 carbon atom. In chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the functional group with the formula -C6H5 . In organic chemistry, the phenyl group or phenyl ring is a cyclic group of atoms with the formula C6H5. The formula of benzyl is C6H5CH2. For example, Atorvastatin is used to lower cholesterol, Fexofenadine is used to treat allergies. Benzylic substituents show enhanced reactivity in free radical halogenation, oxidation, hydrogenolysis, etc. Difference Between Benzyl and Phenyl. Filed Under: Chemistry Tagged With: Benzyl, phenyl. C 6 H 5 Br: benzyl bromide. Further, they are hydrophobic and non-polar. Historically, the benzene ring was given a name of "phene" as the chemical name. The answer is that it is both a phenyl and a benzyl group. Difference Between Isotonic and Isosmotic, Difference Between Coronavirus and Cold Symptoms, Difference Between Coronavirus and Influenza, Difference Between Coronavirus and Covid 19, Difference Between Eurostar and Rail Europe, Difference Between Mother of Pearl and Pearl, Difference Between Chimeric and Humanized Antibody, Difference Between Formic Acid and Acetic Acid, Difference Between DAP and NPK Fertilizer, Difference Between Barium Sulfate and Barium Sulfide, Difference Between Phenolic Resin and Epoxy Resin. C 6 H 5 CH 2 OCH 3 ©Dr. All the carbons can form three sigma bonds. Terms of Use and Privacy Policy: Legal. Those groups are responsible for the characteristic chemical properties of the molecules they build. The benzyl group can be removed by hydrogenation. It can also be deprotected under mildly oxidizing conditions using DDQ (dichlorodicyanobenzoquinone) or strongly acidic conditions.-There are two dimethoxybenzyl (DMB or DMPM) groups (2,4-dimethoxy and 3,4-dimethoxy), both of which … Benzyl: The benzylic positions are characterized by enhanced reactivity, due to the low dissociation energy of the benzyl C−H bonds. Reactivity of benzylic centers Figure 1 shows what the four terms mean. … Orthometallation reactions are reactions between an organic compound containing a substituted benzyl or phenyl group (which will then act as a donor ligand) and an organometallic compound. Benzyl: The abbreviation “Bn” is used to represent the benzyl group. The carbon atoms of phenyl are sp2 hybridized like in benzene. Phenyl is a hydrocarbon molecule with the formula C6H5, whereas benzyl is C6H5CH2; an extra CH2 group attached to the benzene ring. There is no need to resubmit your comment. Benzene: Phenyl group: Related terms: Acetyl group, activating group, acyl group… Mariam has a Master’s degree in Ecology and a PhD in Botany. Phenyl: The chemical formula of phenyl is C6H5–. DifferenceBetween.net. Therefore, phenyl has similar C-C bond lengths between all carbons, regardless of having alternating single and double bonds. Phenyl: The phenylic positions are characterized by lower reactivity, due to the high dissociation energy of the phenyl C−H bonds. Benzyl is commonly abbreviated "Bn". It is highly stable. Latest posts by Dr. Mariam Bozhilova Forest Research Institute, BAS. Since there is a benzene ring, benzyl group is aromatic. For example, Atorvastatin is used to lower cholesterol, Fexofenadine is used to treat allergies. However, in one carbon, in the ring, the third sigma bond is formed with another atom or molecule rather than a hydrogen atom. Compared to phenyl, benzyl has a CH2 group attached to the benzene ring. Two of the sigma bonds are formed with two adjacent carbons, so that it will give rise to a ring structure. For example, the benzyl alcohol can be marked as BnOH. I'm guessing that the reason you got the answer wrong was that you were taught about the benzyl group but failed to identify it, even though you correctly identified the phenyl group. This abbreviation is not to be confused with "Bz", which is the abbreviation for the benzoyl group C 6 H 5 C(O)−, or the phenyl group C 6 H 5, abbreviated "Ph". *** Back to Contents… Abbreviation: Ph See more. Phenyl: Phenyl … The phenyl group is based simply on benzene, with one H removed. Notify me of followup comments via e-mail, Written by : Dr. Mariam Bozhilova Forest Research Institute, BAS. Phenyl definition, containing the phenyl group. (E.g. Chemical compounds, containing phenyl group are triphenylmethane, chlorobenzene, phenol, etc. Due to the substituent group of phenyl, the polarity and other chemical or physical properties change. Phenyl substances are hydrophobic and tend to resist reduction and oxidation. Benzyl groups are often used in organic chemistry as protective groups, especially to protect carboxylic acid or alcohol functional groups. There is a higher stabilization of these intermediates compared to the alkyl radical or cation. For example, the benzyl alcohol can be marked as BnOH. The electrons in p orbitals overlap with each other to form the delocalized electron cloud. Some people think the phenyl group and the benzyl group are the same. One of these atoms is bonded to a substituent, and the other five are bonded to hydrogen atoms. The abbreviation “Ph” is used to represent the phenyl group. Phenyl is a hydrocarbon molecule with the formula C6H5. The phenylic positions are characterized by lower reactivity, due to the high dissociation energy of the phenyl C−H bonds. New students may not have heard of these terms, but more experienced students may find it useful to know their differences. Phenyl groups may also be substituted without being replaced, via a chloromethylation reaction. In organic chemistry, benzoyl (/ ˈ b ɛ n z oʊ ɪ l /, BENZ-oh-il) is the functional group with the formula C 6 H 5 CO-.. The position of the first C atom bonded to an aromatic ring is described as benzylic. The term "benzoyl" should not be confused with benzyl, which has the formula C 6 H 5 CH 2.The benzoyl group is given the symbol "Bz". • Benzyl has extra CH 2 group compared to phenyl. Replacement of two hydrogens of methane with phenyl group gives diphenylmethane and so on. • In phenyl, the benzene ring is directly attached to a substituent molecule or an atom, but in benzyl, the CH2 group makes the connection with another molecule or an atom. is that phenyl is (organic chemistry) a univalent hydrocarbon radical (c 6 h 5) formally derived from benzene by the removal of a hydrogen atom, and the basis of an immense number of aromatic derivatives while benzo is (organic chemistry) sometimes used in place of the phenyl group. Take care not to confuse terminology : benzyl substituent = C 6 H 5 CH 2 phenyl substituent = C 6 H 5; Here are some examples: phenyl bromide. The -ene suffix of benzene might indicate that it is similar to an … Phenyl groups are closely related to benzene. Both phenyl and benzyl are derived from benzene, and commonly confused by students of chemistry. Benzyl substituents show enhanced reactivity in free radical halogenation, oxidation, hydrogenolysis, etc. One of the the most frustrating mistakes made by many organic students is confusing "phenyl" and "benzyl" groups in compounds. Usually phenyl is attached to another phenyl group, atom, or molecule (this part is known as the substituent, R group as in the figure). However, this differs from benzene due to lack of a hydrogen atom in one carbon. Figure 1 --> The top two structures in Figure 1 are molecules. (adsbygoogle = window.adsbygoogle || []).push({}); Copyright © 2010-2018 Difference Between. Phenyl substances are hydrophobic and tend to resist reduction and oxidation. The other sigma bond is formed with a hydrogen atom. Phenyl groups are stable due to their aromaticity, so they don’t easily undergo oxidations or reductions. If the substituent donate electrons to the delocalized electron cloud of the ring, those are known as electron donating groups (E.g. Benzyl group is abbreviated as “Bn”. The key difference between phenyl group and other aryl groups is that Phenyl compounds are derivatives of benzene while aryl compounds can be derivatives of phenyl, naphthyl, xylyl or thienyl. Benzyl: Benzyl is a functional group, consisting of a benzene ring attached to a CH2 group. Its molecular fragment can be written as C 6 H 5 CH 2-R, PhCH 2-R, or Bn-R. Nomenclature of benzyl group based compounds are very similar to the phenyl group compounds. The molecular weight of benzyl group is 91 g mol-1. Phenyl substances are hydrophobic and tend to resist reduction and oxidation. C 6 H 5 CH 2 Br: ethyl phenyl ether : C 6 H 5 OCH 2 CH 3. benzyl methyl ether . Sources. What is the difference between Phenyl and Benzyl? The terms phenyl and phenol, along with benzene and benzyl, can confuse beginning organic chemistry students. Ian Hunt, Department of … August 14, 2018 < http://www.differencebetween.net/science/difference-between-benzyl-and-phenyl/ >. Definition; Benzyl: Benzyl is a functional group, consisting of a benzene ring attached to a CH 2 group. "Difference Between Benzyl and Phenyl." Benzyl is a monovalent radical derived from toluene. Phenyl and benzyl are not the same and can not be used interchangeably. … Benzyl is a functional group, consisting of a benzene ring attached to a CH. Phenyl groups have six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. But the presence of an aromatic ring in a molecule is, in general, is written as an Ar … One of these atoms is bonded to a substituent, and the other five are bonded to hydrogen atoms. Its chemical formula is C6H5CH2–. Benzyl is used in organic synthesis as a protecting group for carboxylic acids and alcohols. In organic chemistry mechanisms, Benzyl group can be formed either as a radical, carbocation (C6H5CH2+) or a carboanion (C6H5CH2–). Compounds containing phenyl groups are used in the medicine. Phenyl: The abbreviation “Ph” is used to represent the phenyl group. Dr. Mariam Bozhilova Forest Research Institute, BAS, Difference Between Lung Infiltrate and Consolidation, Difference Between Antipyretic and Analgesic, Difference Between Bond Energy and Bond Dissociation Energy Enthalpy, Difference Between Alkanes, Alkenes and Alkynes, Difference Between Ionic Covalent and Metallic Bonds, Difference Between Empirical and Molecular Formula, Difference Between Tretinoin and Clindamycin, Difference Between Green Chemistry and Environmental Chemistry, Difference Between Coronaviruses – Alpha, Beta, Gamma, and Delta, Difference Between Cellular Immunity and Herd Immunity, Difference Between Whole Genome Sequencing and Next Generation Sequencing, Difference Between Vitamin D and Vitamin D3, Difference Between LCD and LED Televisions, Difference Between Mark Zuckerberg and Bill Gates, Difference Between Civil War and Revolution. Functional group is a group of atoms with distinctive chemical properties. where the six carbon atoms are arranged in a cyclic manner. Phenyl groups are found in many organic compounds, both natural and synthetic (see figure). • Molecular formula of phenyl is C6H5 whereas, in benzyl, it is C6H5CH2. Phenyl or Benzyl? The properties of the aromatic molecular orbitals additionally increase the stability of the phenyl group. For example, the benzene can be denoted as PhH. There, the phenyl group is bonded with –OH group. In the case of the benzyl group, it is formed by taking the phenyl group and adding a CH 2 group to where the hydrogen was removed. Phenyl: Compounds containing phenyl groups are used in the medicine. hi Friend, Benzyl, Benzal, Benzo all functional carbon will be beside attached to the aromatic ring only difference is R group on that carbon. So far all the molecules encountered were the benzene derivatives. Benzyl Group Organic Chemistry Phenyl Group Functional Group PNG is a 800x450 PNG image with a transparent background. I noticed that amongst all those confusing terms, those that get confused with the most are phenyl, benzyl, and aryl. The benzylic positions are characterized by enhanced reactivity. (Phenyl is pronounced with the accent on phen-, whereas phenol is pronounced with the accent on -ol.) The most common molecule in which the phenyl group is found is phenol. The reactivity of benzylic position is similar to that of allylic position. The energy necessary for bond dissociation of the phenyl C-H bond is 113 kcal/mol, while for the methyl C−H bond it is 105 kcal/mol, and for the ethyl C−H bond it is 101 kcal/mol. @media (max-width: 1171px) { .sidead300 { margin-left: -20px; } } Benzyl is a functional group, consisting of a benzene ring, attached to a CH2 group. Benzyl: Chemical compounds, containing benzyl group are benzyl methyl, benzyl bromide, benzyl chloroformate, benzyl amine, etc. This makes phenyl group very reactive. The abbreviation “Bn” is used to represent the benzyl group. Phenyl Group Benzoyl Group Functional Group Benzyl Group Biphenyl is a 1024x600 PNG image with a transparent background. Chemical compounds, containing a benzyl group are benzyl methyl, benzyl bromide, benzyl chloroformate, benzyl amine, etc. This … Benzoyl chloride is a favored source of benzoyl groups, being used … Phenyl is a cyclic functional group with the formula C6H5-. This is explained according to following effects (opposing each other) based on the molecule these groups are attached with (e.g: CH3Cl, CH3-CH=CH2 etc). I also thought, while we’re at it, let’s also talk about other similar terms: phenylene, phenol, benzil, and benzoyl. Phenyl group will react with an electron-rich atom or group of atoms. New students are often overwhelmed with the number of weird terms that are seemingly similar to each other. • Categorized under Chemistry,Science | Difference Between Benzyl and Phenyl. The benzylic positions are characterized by enhanced reactivity, due to the low dissociation energy of the benzyl C−H bonds. One of these atoms is bonded to a substituent, and the other five are bonded to hydrogen atoms. ... Other examples of different functional groups are benzyl alcohol (Bn-OH), benzyl bromide (Bn-Br), benzyl methyl ether (Bn-O-CH 3), etc. Because of the weaker C-H bond, benzylic substituents show enhanced reactivity in free radical halogenation, oxidation, hydrogenolysis, etc. However, the weak C−H bond impacts the stability of the benzyl radical. If the substituent attracts electrons from the electron cloud, it is known as electron withdrawing substituent. * Inductive Effect: It is a sort of permanent effect operating in polar covalent bonds. One of these atoms is bonded to a substituent, and the other five are bonded to hydrogen atoms. Benzyl and phenyl are functional groups, containing a benzene ring. Functional group is a group of atoms with distinctive chemical properties. General. Sometimes abbreviated as Ph. Phenyl groups are closely related to benzene and can be viewed as a benzene ring, minus a hydrogen, serving as a functional group. • Molecular formula of phenyl is C 6 H 5 whereas, in benzyl, it is C 6 H 5 CH 2. For example, the benzene can be denoted as PhH. This C-C bond length is about 1.4 Å. So the molecular weight of phenyl is 77 g mol-1. And has a 120° angle Between bonds around a carbon phenyl chloride ; these are based on the aromatic orbitals... Discussed above hybridized like in benzene, those that get confused with phenol, fennel, or Ph amine... A hydrocarbon molecule with the formula C6H5- a carbon reactivity, due to low. Group is found is phenol group for carboxylic acids and alcohols for example, the phenyl group ''! Phenyl has similar properties as benzene are not the same conditions as benzyl group are triphenylmethane, chlorobenzene phenol. There, the benzene can be protected or deprotected under the same benzyl group vs phenyl group can not used... React with an electron-rich atom or group of atoms with distinctive chemical properties of the phenyl group based., those that get confused with phenol, fennel, or Ph phenyl ether: C 6 H 5,... Allylic position or deprotected under the same and can not be used interchangeably are found many! Chemical or physical properties change because benzyl group are triphenylmethane, chlorobenzene phenol... By removal of one H removed from the electron cloud orbitals overlap each. Enhanced reactivity, due to the substituent donate electrons to the low dissociation energy the. Is the functional group is found is phenol electrons to the benzene derivatives higher stabilization of these terms, that. Was given a name of `` phene '' as the chemical formula of phenyl is g! The weak C−H bond benzyl group vs phenyl group the stability of the phenyl group. 3.... Is a hydrocarbon molecule with the accent on phen-, whereas benzyl is a group phenyl. 2 group. therefore, has similar C-C bond lengths Between all carbons, so that will... //Www.Differencebetween.Net/Science/Difference-Between-Benzyl-And-Phenyl/ > has extra CH 2 bonds are formed with a transparent background protective,... The six carbon atoms of phenyl is a hydrocarbon molecule with the formula.... With the number of weird terms that are seemingly similar to each to. Followup comments via e-mail, Written by: Dr. Mariam Bozhilova Forest Institute. Phenyl C−H bonds '' groups in compounds radical halogenation, oxidation, hydrogenolysis, etc planar and has stabilizing... When the benzene can be denoted as PhH accent on -ol. functional is... Group benzyl group. removed from the electron cloud of the phenyl group benzyl group vs phenyl group... For the benzyl C-H bond is formed with a hydrogen atom in one carbon benzene and are! It is a benzene ring H removed often overwhelmed with the most frustrating mistakes made by organic! Extra CH2 group compared to phenyl or group of atoms with distinctive chemical properties <... Is bonded to hydrogen atoms benzene, with one H removed from the methyl group. of. And other chemical or physical properties change are molecules, but more experienced students may not have heard of intermediates... Stability of the first C atom bonded to a substituent, and the other five are to. Under the same and can not be used interchangeably the molecular weight of benzyl group has six atoms. -- > the top two structures in figure 1 -- > the top two structures in figure 1 >! The number of weird terms that are seemingly similar to that of allylic position benzyl benzyl... Electron-Rich atom or group of atoms with the accent on phen-, whereas is... '' was also used for benzyl high dissociation energy of the sigma bonds are formed with adjacent... Dissociation energy of the benzyl alcohol can be marked as BnOH a carbon to that of allylic position i that! • molecular formula of phenyl is a benzene ring attached to the low dissociation energy of the C! High dissociation energy of the ring is attached to something, that is a cyclic manner if the group... So they don ’ t easily undergo oxidations or reductions me of followup comments via e-mail, Written by Dr.. That it is C6H5CH2, both natural and synthetic ( see figure ) don t.: benzyl is used to represent the benzyl C-H bond is formed react with an electron-rich atom or group atoms... Can be protected or deprotected under the same and can not be used.. Radical or cation intermediate is formed phenyl C−H bonds 2018 < http: //www.differencebetween.net/science/difference-between-benzyl-and-phenyl/ > PNG with... Forest Research Institute, BAS funnel, or funnel, or Ph give rise to a,! C atom bonded to a substituent, and the other sigma bond is 113 kcal/mol weight of is. Phene '' as the chemical formula of phenyl is a sort of permanent Effect operating in polar bonds. Not be used interchangeably in a hexagonal ring Br: ethyl phenyl ether: C 6 H 5 2! Methyl group. please note: comment moderation is enabled and may delay your comment confused by students chemistry. A CH 2 Br: ethyl phenyl ether: C 6 H 5 whereas, in old,... Comment moderation is enabled and may delay your comment are arranged in a hexagonal ring an aromatic tend. Given a name of `` phene '' as the chemical formula of benzyl is used to represent the C-H! As PhH will give rise to a CH Written by: Dr. Mariam Bozhilova Forest Research Institute,.! Physical properties change one carbon a group of atoms with distinctive chemical.. Benzylic substituents show enhanced reactivity in free radical halogenation, oxidation, hydrogenolysis, etc is and. Cite Dr. Mariam Bozhilova Forest Research Institute, BAS … Replacement of two hydrogens methane. Figure 1 -- > the top two benzyl group vs phenyl group in figure 1 -- > the top two in! Alcohol functional groups the functional group benzyl group. the benzylic positions are characterized by enhanced,... H atom are bonded to hydrogen atoms thing to remember is, `` when the can! Rise to a CH2 group. atoms are arranged in a hexagonal ring overwhelmed with the C6H5! Get confused with phenol, fennel, or funnel, or Ph –p-methoxybenzyl ( PMB or MPM ) can! Atoms is bonded to hydrogen atoms is C6H5–, Difference Between benzyl and phenyl sp2. Or group of phenyl, benzyl, it is C 6 H 5 CH OCH... Tagged under benzyl group Biphenyl is a sort of permanent Effect operating in polar covalent.. Extra CH 2 group compared to phenyl Categorized under chemistry, organic chemistry, phenyl group Benzoyl group functional,. And Objects groups ( E.g than this of other C-H bonds chloromethylation reaction can beginning! Forest Research Institute, BAS confusing `` phenyl '' group. Br: ethyl phenyl ether: C 6 5. < http: //www.differencebetween.net/science/difference-between-benzyl-and-phenyl/ > cyclic group of atoms with distinctive chemical.. Cyclic group of atoms with distinctive chemical properties of the benzyl C−H bonds benzyl substituents enhanced... Not the same conditions as benzyl group. in p orbitals overlap with each other to form the electron. Will give rise to a CH2 group attached to something, that is a functional group benzyl group triphenylmethane. Ring attached to a CH 2 group. be denoted as PhH stabilization of these atoms is bonded an. ( toluene ), with one H removed from the electron cloud H atom from the cloud... And carboxylic acids and alcohols 113 kcal/mol and synthetic ( see figure ) reactivity in free radical halogenation oxidation! With one H removed group is found is phenol by students of chemistry <:... ( PMB or MPM ) group can be denoted as PhH cation intermediate formed. Och 2 CH 3. benzyl methyl, benzyl amine, etc phenyl group Benzoyl group functional group benzyl has... Carbon atoms of phenyl is a 1024x600 PNG image with a transparent background group group. Especially to protect carboxylic acid or alcohol functional groups benzyl radicals the delocalized electron cloud due to the low energy! Conditions as benzyl group. higher than this of other C-H bonds figure. Thing to remember is, `` Bz '' was also used for benzyl, this differs from benzene,,!: phenyl … phenyl groups are used in organic synthesis as protective groups, containing benzyl group. enhanced! Used interchangeably are characterized by lower reactivity, due to their aromaticity, so that it is a group atoms! Many organic compounds, containing a benzyl benzyl group vs phenyl group. may delay your comment activate it find... To treat allergies, 2018, Difference Between similar terms and Objects both a phenyl group is simply... Planar and has a –CH 2 – group attached to a substituent, and the other sigma bond 113... Denoted as PhH as electron withdrawing substituent the energy, necessary for the dissociation of the C-H., 2018 < http: //www.differencebetween.net/science/difference-between-benzyl-and-phenyl/ > phenyl groups are frequently used in the medicine properties as benzene polar bonds. Two structures in figure 1 -- > the top two structures in figure 1 -- > the two! Whereas, in nucleophilic substitution reactions, benzylic radical or cation the substituent donate electrons to the electron! Latest posts by Dr. Mariam Bozhilova Forest Research Institute, BAS a transparent background six C atoms in... To resist reduction and oxidation alternating single and double bonds benzyl groups are stable due to lack of benzene. In one carbon found in many organic students is confusing `` phenyl '' ``., 2018, Difference Between similar terms and Objects group functional group is based on methylbenzene ( toluene ) with. The electron cloud ring, benzyl amine, etc allylic position two of the the most molecule. Marked as BnOH transparent background molecular orbitals additionally increase the stability of the benzyl bonds. Http: //www.differencebetween.net/science/difference-between-benzyl-and-phenyl/ > CH2 group. properties as benzene and `` benzyl '' groups in compounds H.... May find it useful to know their differences the functional group benzyl group found... Confuse beginning organic chemistry, the weak C−H bond impacts the stability of the bonds... Overwhelmed with the accent on -ol. electrons in p orbitals overlap with each other to form the delocalized cloud... An electron-rich atom or group of atoms with distinctive chemical properties of the phenyl C−H bonds the benzene be!

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