We are asked to order the following compounds considering their hydrolysis.
1)CH3COCl
2)CH3CO-C2H5
3)CH3-CO-N:H2
4) CH3-CO-O-CH3
What are the main factors which determine how easily they tend to hydrolysis?
The main factors that determine how easily compounds tend to undergo hydrolysis are:
1) Nature of the leaving group: In hydrolysis reactions, a leaving group is replaced by a hydroxide ion (OH-) or a water molecule. Compounds with weaker or more easily displaced leaving groups (such as Cl-) tend to hydrolyze more readily.
2) Stability of the product: The stability of the product formed after hydrolysis also influences the tendency of a compound to undergo hydrolysis. If the product formed is more stable, the compound will tend to hydrolyze more easily.
3) Steric hindrance: Compounds with bulky substituents may experience steric hindrance, which can hinder the approach of water molecules or hydroxide ions to the reaction site. This can decrease the rate of hydrolysis.
4) Resonance stabilization: Compounds with resonance stabilization may be less prone to hydrolysis because the resonance delocalization of electrons provides extra stability and makes it harder for the reaction to occur.
Now, let's consider the order of hydrolysis for the given compounds:
1) CH3COCl: This compound contains an acyl chloride functional group (R-CO-Cl). Acyl chlorides are known to be highly reactive towards hydrolysis due to the presence of the strong leaving group (Cl-) and the absence of resonance stabilization. Therefore, it undergoes hydrolysis fairly easily.
2) CH3CO-C2H5: This compound is an ester (R-CO-OR'), where R is an acetyl group and R' is an ethyl group. Esters are less reactive towards hydrolysis compared to acyl chlorides because their leaving groups (-OR') are weaker. However, esters can still undergo hydrolysis under acidic or basic conditions.
3) CH3-CO-N:H2: This compound is an amide (R-CO-NH2), which contains a nitrogen atom bonded to the carbonyl carbon. Amides are generally less reactive towards hydrolysis compared to acyl chlorides and esters due to the presence of the nitrogen atom, which provides additional stabilization through resonance delocalization of electrons.
4) CH3-CO-O-CH3: This compound is an ester similar to compound 2. However, in this case, the ester group is methyl acetate, which contains a methyl group as the R' substituent. This compound is comparable to compound 2 regarding its hydrolysis tendency.
Therefore, the order of hydrolysis from most to least reactive is:
1) CH3COCl
2) CH3-CO-O-CH3
3) CH3CO-C2H5
4) CH3-CO-N:H2