Are Alkyl Groups Electron Donating

Are Alkyl Groups Electron Donating add electron density

What are electron donating groups examples?

Determine the ortho/para position of BR atom in benzene ring… This makes it appear as though the alkyl groups ‘donate’ electron density towards the heteroatom . See how hydrogen has been assigned the value #2.20#, whilst carbon is #2.55#? This means that, in a #"C"-"H"# covalent bond, electrons have a greater tendency to be drawn towards the carbon atom; in other words, they spend more time in the carbon atom’s local region. Electronegativity is defined as the tendency of an atom of an element to draw electrons towards itself in a covalent bond. Electronegativity is a property of an element, and it is the arbitrary Pauling scale that represents how electronegative each element is.

The arguments are pretty similar though, since inductive effects are conveyed through the coupling of the orbitals as well. If I’m not mistaken (and I could easily be, since this is several years since I’ve last thought about this), there are two reasons for alkyl groups being electron donating. Is there any good explanation for why alkyl groups donate electron density?

Activating substituents favour electrophilic substitution about the ortho and para positions. Weakly deactivating groups direct electrophiles to attack the benzene molecule at the ortho- and para- positions, while strongly and moderately deactivating groups direct attacks to the meta- position. This is not a case of favoring the meta- position like para- and ortho- directing functional groups, but rather disfavouring the ortho- and para-positions more than they disfavour the meta- position.

  • The effect is illustrated for electrophilic aromatic substitutions with alkyl substituents of differing steric demand for electrophilic aromatic nitration.
  • Electron donating groups are said to be ortho/para directing and they are activators.
  • Since- I effect of Chlorine is stronger than it’s +R effect hence Cl causes net deactivation.
  • Fluorine is something of an anomaly in this circumstance.

This too is noticed in the case of carbocations, but is also seen in other molecules. The inductive (in this case, +I) effect is nothing but a charge redistribution between two species with a difference in electronegativity. It is identical to the polarity induced in say, the H-Cl bond due to this difference.

This is a similar effect to that for type 1 except that the electrons are from a bonded pair not a lone pair. Due to the lone pair of electrons, halogen groups are available for donating electrons. The inductive and resonance properties compete with each other but the resonance effect dominates for purposes of directing the sites of reactivity. For nitration, for example, fluorine directs strongly to the para position because the ortho position is inductively deactivated (86% para, 13% ortho, 0.6% meta). On the other hand, iodine directs to ortho and para positions comparably (54% para and 45% ortho, 1.3% meta). Hence these sites are less nucleophilic, and so the system tends to react with electrophiles at the meta sites.

Since the halogens are very electronegative they cause inductive withdrawal . Although many of these groups are also inductively withdrawing (–I), which is a deactivating effect, the resonance effect is almost always stronger, with the exception of Cl, Br, and I. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below. (-M) is an electron-withdrawing group that ‘pulls’ electrons out from the carbon atom and the rest of the structure it is attached to. H+ is one of the only electrophiles that is guaranteed to be an electrophile.

Is OCH3 an activator?

When both group have similar directing effect and are para to each other, the third substituent depends on the less hindered one. Halogens are also electron-withdrawing; the effect gets weaker going down the group. To understand the effects of EWGs and EDGs on nucleophile and electrophile strength. To recall the definitions of electron-withdrawing group and electron-donating groups .

These cations hang around long enough to undergo various other reactions before the elimination reaction can occur. So, think about drawing the conversion of the carbocation to the alkene without completely breaking that C-H bond and not completely forming the C-C double bond; think about it that way. The more electron rich a nucleophile, or electron poor the electrophile, the better.

An alkyl group is formed by removing one hydrogen from the alkane chain and is described by the formula CnH2n+1….Alkyl Groups. However, some groups, such as the alkyl group, are less electron-withdrawing than hydrogen and are therefore considered as electron-releasing. This is electron-releasing character and is indicated by the +I effect. In short, alkyl groups tend to give electrons, leading to the induction effect. An alkyl group is formed by removing one hydrogen from the alkane chain and is described by the formula C nH 2n +1. When both an ortho/para director and a meta director is present on the ring, the third substituent’s place depends on the ortho/para director.

This is because of the smaller HOMO-LUMO gap discussed in Nucleophiles and electrophiles. These conditions will lead to greater reactivity and a higher product yield; the smaller the HOMO-LUMO gap, the greater tendency for reactant bonds to break and product bonds to form. With your question, -OCH3 is a larger molecule and will more easily donate electrons , but it is also a weaker base than -OH. Hence it would feed electrons to the bond to increase the number of resonance structures, which would in turn increase the stability of the compound. Carboxylic acid is a much better acid than the equivalent alcohol, so it results in a more stable ion as it lacks its proton.

Activating groups

On top of that, it’s fun – with achievements, customizable avatars, and awards to keep you motivated. Our proven video lessons ease you through problems quickly, and you get tonnes of friendly practice on questions that trip students up on tests and finals. Due to strong nuclear charge in case of F , F has high electron affinity than I. Nitro groups are electron-withdrawing groups, so bromine adds to the meta position.

The generally electropositive nature of the alkyl group with respect to others makes it be electron donating. This is particularly noticeable in carbocations because of the large electronegativity of the C+ atom. Groups having negative charge or at least one lone pair of electrons and donate electrons to the benzene ring show resonance effect. Resonance effect is the delocalization of $pi $ electrons. Electron donating groups are typically divided into three levels of activating ability (The “extreme” category can be seen as “strong”.) Electron withdrawing groups are assigned to similar groupings. Due to the electronegativity difference between carbon and oxygen / nitrogen, there will be a slight electron withdrawing effect through inductive effect (known as the –I effect).

Some atoms or groups are electron-withdrawing when bound to a carbon, as contrasted with a hydrogen atom in the same position. Electron donating groups on a benzene ring are said to be activating, because they increase the rate of the second substitution so that it is higher than that of standard benzene. Electron donating groups are said to be ortho/para directing and they are activators. Hence any atom with a greater electronegativity can and does exert an attraction on the neighbouring bonding electrons of the alkyl group. The bigger the alkyl group the more electron density ‘available’ for attraction.

This causes the ortho and para products to form faster than meta. There are 2 ortho positions, 2 meta positions and 1 para position on benzene when a group is attached to it. However, the partial rate factors at the ortho and para positions are not generally equal. In the case of a fluorine substituent, for instance, the ortho partial rate factor is much smaller than the para, due to a stronger inductive withdrawal effect at the ortho position. Aside from these effects, there is often also a steric effect, due to increased steric hindrance at the ortho position but not the para position, leading to a larger amount of the para product. It is due to the difference in electronegativity between carbon and hydrogen.

However, the other effect called resonance add electron density back to the ring (known as the +M effect) and dominate over that of inductive effect. Hence the result is that they are EDGs and ortho/para directors. Alkyl substituents (e.g. -CH3, -CH2CH3) are also electron donating groups – they activate the aromatic ring by increasing the electron density on the ring through an inductive donating effect.

An electrophilic addition reaction is an addition reaction which happens because what we think of as the “important” molecule is attacked by an electrophile. The “important” molecule has a region of high electron density which is attacked by something carrying some degree of positive charge. In this case, the inductive effects pushes electron density onto the carboxylate anion, producing a destabilizing effect, decreasing the acidity of the carboxylic acid. A methoxy group is the functional group consisting of a methyl group bound to oxygen.

Thus, we can use these simple species, whose π electron distribution can be calculated using simple Hückel theory, as models to rationalize the regiochemical outcome of electrophilic aromatic substitution. As can be seen, the π electron population at the ortho and para positions is depleted for the case of an electron-withdrawing group, causing meta attack to be occur as the least disfavourable option. The consideration of resonance forms is useful in this regard, since they provide a convenient means of determining the locations of these perturbations. A carbon atom with a larger coefficient will be preferentially attacked, due to more favorable orbital overlap with the electrophile. Since- I effect of Chlorine is stronger than it’s +R effect hence Cl causes net deactivation.

Thus, electrophilic aromatic substitution on fluorobenzene is strongly para selective. The lone pair of an electron in a chlorine atom stabilizes the intermediate carbocation due to resonance. … Chlorine withdraws electrons through inductive effect and releases electrons through resonance. Hence, chlorine is ortho, para-directing in electrophilic aromatic substitution reaction. Since NO2 is an electron withdrawing group, a glance at the resonance structures shows that the positive charge becomes concentrated at the ortho-para positions.

This means that there are electrons in its valence shell that have not participated in covalent bonding. The alkyl group’s tendency to donate electrons derives from this fact. Carbon is more electronegative than hydrogen; therefore, its tendency to donate electrons as part of an alkyl group is increased.

This can be useful as it stops it attacking an electrophile but it may be too hindered to act as a base as well. A good compromise is Et3N, which is a strong base but too hindered to attack most things. When both group are the same director, the third substituent depends on the stronger one.

… Whereas the Br+ ion is very unstable and to attain stability it takes part in chemical reaction. Since Br+ wants to gain electron to attain stability, so it is an. As you can see, nucleophiles all have pairs of electrons to donate, and tend to be rich in electrons.