Frequent question: Which cyclic ketone in a mine is most reactive?

Cyclic ketone enamines follow a reactivity trend where the five membered ring is the most reactive due to its maximally planar conformation at the nitrogen, following the trend 5>8>6>7 (the seven membered ring being the least reactive).

Which is more reactive ketone or ester?

Since the -OR group is a stronger electron donor (resonance) than the alkyl group of the ketone, the ester is less reactive than the ketone… so we get : (b) The aldehyde, carboxylic acid and ester will be reduced to the same product, benzyl alcohol.

Which is the most reactive carbonyl compound?

The partial positive charge on an aldehyde carbonyl carbon is less stable than the partial positive charge on a ketone carbonyl carbon. Again, aldehydes are more reactive than ketones.

Why are imines more reactive than aldehydes?

The reason usually cited (see pages 2-4 of this reference) for this behavior is that the imine double bond is less polarized than the carbonyl double bond. … This will make the protonated imine carbon much more electrophilic (positively polarized).

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Which is more reactive carboxylic acid or aldehyde?

The relative reactivity of carboxylic acid derivatives

As a general rule, the carbonyl carbon in an acyl group is less electrophilic than that in an aldehyde or ketone. … Carboxylic acids and esters are in the middle range of reactivity, while thioesters are somewhat more reactive.

Why are acid anhydrides so reactive?

Thus, acid chlorides are more reactive than anhydrides, which are more reactive than esters, which are more reactive than amides. This is due to the electronegative group, such as chlorine, polarizing the carbonyl group more strongly than an alkoxy group (ester) or an amino group (amide).

Is ketone a good Nucleophile?

2 Answers. The ester carbonyl carbon is a stronger nucleophile and less prone to nucleophilic attack than the carbonyl carbon in a ketone. … Therefor a nucleophile will react faster with a ketone carbonyl than an ester carbonyl.

Are carbonyl groups reactive?

Because of the greater electronegativity of oxygen, the carbonyl group is polar, and aldehydes and ketones have larger molecular dipole moments (D) than do alkenes. … The polarity of the carbonyl group also has a profound effect on its chemical reactivity, compared with the non-polar double bonds of alkenes.

Which is the least reactive carbonyl compound?

So Acetophenone will be the least reactive towards nucleophilic addition reactions among the given carbonyl compounds. Acetophenone is the answer.

Are carboxylic acids reactive?

Among the carboxylic acid derivatives, carboxylate groups are the least reactive towards nucleophilic acyl substitution, followed by amides, then carboxylic esters and carboxylic acids, thioesters, and finally acyl phosphates, which are the most reactive among the biologically relevant acyl groups.

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Which is more stable aldehyde or ketone?

ketones are more stable because alkyl groups are weak electron donor groups so they can compensate partially positive charge on the carbonyl carbon donating some of the negative charge. aldehydes have only one alkyl group so the compensating is much lower.

Which is more reactive formaldehyde or acetaldehyde?

Secondly , CH3 group in acetaldehyde decreases the positive charge on cabonyl carbon by +I effect to some extect which is not so in the case of formaldehyde, Since , Nu attack is favourable with more positive charge and less hinderance at carbonyl carbon , hence we conclude that formaldehyde is more reactive than …

Why imine is more stable than Enamine?

Imines are similar to aldehydes and ketones in a lot of ways. An imine is a functional group or chemical compound containing a carbon–nitrogen double bond. … Imines are more stable than enamines and an enamine will form only if the formation of the imine is not possible.

Why are amides the least reactive carboxylic acid derivative?

Resonance electron donation by Y decreases the electrophilic character of the carbonyl carbon. The strongest resonance effect occurs in amides, which exhibit substantial carbon-nitrogen double bond character and are the least reactive of the derivatives.

Is an alcohol more reactive than a ketone?

An alcohol is more polar than a ketone because it can engage in hydrogen bonding with more molecules of itself or with polar solvents. A ketone can hydrogen bond with other polar molecules with acidic hydrogens, but it cannot hydrogen bond with itself.

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Why is acyl chloride more reactive?

Acyl chlorides are the most reactive carboxylic acid derivatives. The electronegative chlorine atom pulls electrons toward it in the C-Cl bond, which makes the carbonyl carbon more electrophilic. This makes nucleophilic attack easier. Also, the Cl- is an excellent leaving group, so that step is also fast.