What Makes A Good Leaving Group?: - Ots (Better) - I - BR - CL - F - H20 (Worse)

Leaving Groups -OTs (better) -I -Br -Cl -F -H20(worse)
What makes a good leaving group?

Any time a new bond is formed, take a look at the atom thats accepting the lone pair of electrons. Does it have a full shell of electrons? Oftentimes it does. If so, that means youre going to have to break a bond thats attached to that atom. If its a single bond youre breaking, what you end up creating is called a leaving group.
Note how the second arrow always shows a pair of electrons going toward the leaving group. That means the charge on it is going to become more negative by 1 when it leaves. So if the leaving group is positively charged, it will become neutral, and if its neutral, it will become negative. The identity of the leaving group is crucial to whether the reaction will happen at all. There are good leaving groups and there are bad leaving groups. Reactions are more likely to take place when you can displace a good leaving group. What makes a leaving group good or bad? Thankfully, theres one simplifying factor to look at when deciding this: its basicity. Good leaving groups are weak bases. How do we know what are weak bases? Theres a useful tool for that its called a pKa table. Many pKa tables only specifically give you the identity of the acid, but if you think about it, it also gives you information about the conjugate base of each acid. The conjugate base is the part left over when you lose H+. The stronger the acid, the weaker the conjugate base. And the weaker the conjugate base, the better the leaving group. So a pKa table is a great guide to leaving group ability.
One word of caution: pKa measures an equilibrium, whereas leaving group ability is based on reaction rates. So although the correlation is very good, it isnt perfect. Heres a pKa table, annotated.
The trend is pretty clear in general, the weaker the base, the better the leaving group. Furthermore, note how we (almost) never see alkanes or hydrogens as leaving groups. Thats because theyre strongly basic anions and very unstable.
You might note that I have carefully avoided discussing fluorine. Fluorine tends to be a very poor leaving group for SN1/SN2/E1/E2 reactions. In Org 2, you may see some examples where F can act as a leaving group when it is attached to a carbonyl carbon or an aromatic ring. These reactions (addition-elimination reactions) are a little bit different in that the rate determining step is not so related to loss of the leaving group. There are some extra factors at work in these situations that we can discuss if youre curious.
Leaving group
From Wikipedia, the free encyclopedia In chemistry, a leaving group is a molecular fragment that departs with a pair of electrons in heterolytic bond cleavage. Leaving groups can be anions or neutral molecules. Common anionic leaving groups are halides such as Cl, Br, and I, and sulfonate esters, such as paratoluenesulfonate ("tosylate", TsO). Common neutral molecule leaving groups are water (H2O), and ammonia.
In this SN2 reaction, bromide (Br) acts as the leaving group and hydroxide (OH) as the nucleophile. The ability of a leaving group to depart is correlated with the pKa of the conjugate acid, with lower pKa being associated with better leaving group ability. The correlation is not perfect because leaving group ability is a kinetic phenomenon, relating to a reaction's rate, whereas pKa is a thermodynamic phenomenon, describing the position of an equilibrium. Nevertheless, it is a general rule that more highly stabilized anions act as better leaving groups. Consistent with this rule, strong bases such as alkoxide (RO), hydroxide (HO), and amide (R2N) are poor leaving groups. Leaving groups ordered approximately in decreasing ability to leave [1] *R-N2+ diazonium salts + R-OR'2 oxonium ions R-OSO2C4F9 nonaflates R-OSO2CF3 triflates R-OSO2F fluorosulfonates R-OTs, R-OMs, etc. tosylates, mesylates, and similar R-I iodides R-Br bromides + R-OH2 (Conjugate acid of an alcohol) R-Cl chlorides, and acyl chloride when attached to carbonyl carbon + R-OHR' Conjugate acid of an ether
R-ONO2, R-OPO(OH)2 nitrates, phosphates, and other inorganic esters R-SR'2+ R-NR'3+ tetraalkylammonium salts R-F fluorides R-OCOR esters, and acid anhydrides when attached to carbonyl carbon + R-NH3 ammonium salts R-OAr phenoxides R-OH alcohols, and carboxylic acids when attached to carbonyl carbon R-OR ethers, and esters when attached to carbonyl carbon
It is uncommon for groups such as H- (hydrides), R3C- (alkyl anions, R=alkyl or H), or R2N- (amides, R=alkyl or H) to depart with a pair of electrons because of the instability of these bases. However, the requirement for a good leaving group is relaxed in the case of E1cb mechanisms, such as the elimination step in the addition-elimination mechanism of nucleophilic acyl substitutions. Here, alkoxides and even amides can act as leaving groups due to the entropic favorability of having one molecule split into two. SPARKS NOTES Leaving Groups and Nucleophiles
The leaving group is a component of every substitution and elimination reaction discussed in this SparkNote. As such, it makes sense to learn the characteristics of a good leaving group. In any substitution or elimination reaction, electrons from a nucleophile, carbon-hydrogen bond, or the solvent break a carbon-leaving group bond. Here the leaving group is abbreviated as "LG."
As you can see, the leaving group is aptly named; it is the group that leaves.
There is a bit of terminology dealing with the leaving group important to substitution and elimination. The -carbon is the carbon atom bonded to the leaving group. -carbons are attached to the -carbon. The hydrogens attac hed to the -carbon are called -hydrogens. This terminology is vitally important for our discussion of substitution and elimination reactions.
Ranking Leaving Groups
Let's define a good leaving group as one that leaves easily. Then the effectiveness of a leaving group increases with the group's energetic stability after it has left. Thus a weak base is a better leaving group than a strong base. Likewise, a m olecule that is neutral after leaving is generally a better leaving group than one that is negatively charged after leaving. Halides and the tosyl group (-OTs) are examples of commonly used leaving groups. In general, if the group is relatively stable after leaving the molecule with the C-LG bond's electrons, it's a good candidate for a leaving group.

What Makes A Good Leaving Group?: - Ots (Better) - I - BR - CL - F - H20 (Worse)

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Leaving Groups -OTs (better) -I -Br -Cl -F -H20(worse)

What makes a good leaving group?

Ranking Leaving Groups

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