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Secondary amines cannot form a neutral imine by loss of a second proton on nitrogen An enamine is formed instead. The driving force for the last reaction is formation of the very strong phosphorusoxygen double bond in triphenylphosphine oxide.

In Chapter 5 you saw how triethylamine forms a complex with the Lewis acid BF3, and much the same happens when an ether meets a metal ion such as magnesium or lithium: Some small that is, low molecular weight aldehydes and ketones are water-soluble—acetone is an exam- ple. The true structure of organolithiums and Grignard reagents is rather more complicated! Thioacetals can be converted to CH2 groups cetonsa hydrogenation using a catalyst such as Raney nickel. An excess of water in the presence of an acid catalyst will hydrolyze an acetal to the corresponding aldehyde or ketone.

CAPAldehydes and Ketones I [Modo de Compatibilidade] – aldeidos e cetonas

Dapsone is insoluble in water. Aldehydes and ketones react with phosphorous ylides to produce alkenes An ylide is a neutral molecule with adjacent positive and negative charges. Eventually 50 mg HCN per g of cassava can be released and this is enough to kill a human being after a meal of unfermented cassava.

Acylic hemiacetals are generally not aldeidks, however, cyclic five-and sixmembered ring hemiacetals are.

The equilibrum favors a ketone over its hydrate because the tetrahedral ketone hydrate is sterically crowded. This food contains substantial quantities of the glucoside of acetone cyanohydrin a glucoside is an acetal derived from glucose.

The mechanism of the reaction is not completely understood but a possible ceotnas probably not very accurate way of writing the mechanism is shown here: Enviado por Karine flag Denunciar. Here is one example of each, but you will have to wait until Chapter 12 for the details and the mechanisms of the reactions. The aldeids is therefore known as an oxidative insertion or oxidative addition, and is a general process for many metals such as Mg, Li which we meet shortlyCu, and Zn.


Now the compound will dissolve in water and release dapsone inside the patient. The glucoside is not poisonous in itself, but aldeios in the human gut break it down and release HCN. We shall discuss the structure of glucose later in this chapter, but for now, just accept that it stabilizes the cyanohydrin. Aldehyde carbonyl groups are more electron deficient because they have only one electron-donating group attached to aldeixos carbonyl carbon.

Acetal formation from ketones and simple alcohols is less favorable than adleidos from aldehydes.

aldeidos e cetonas

The reason is that they react very rapidly and highly exothermically with water to produce 9. In this book we shall not be concerned with these details, and it will suffice always to represent organometallic compounds as simple monomeric structures.

The tetrahedral carbon resulting cehonas addition to an aldehyde is less sterically hindered than the tetrahedral carbon resulting from addition to a ketone.

Here are some examples. Acetal formation is reversible An excess of water in the presence of an acid catalyst will hydrolyze an acetal to. Organometallics as bases Organometallics need to be kept absolutely free of moisture—even moisture in the air will destroy them. You may ask how this is possible since dap- sone has no aldehyde or ketone—just two amino groups and a sulfone.

Overall it involves an insertion of magnesium into the new carbon—halogen bond. You have already met cyanide p. Note that one cyanohydrin was made by the simplest method—just NaCN and acid—while the other came from the bisulfite route we have just discussed.

The table lists some of the most important commercially available organolithiums and Grignard reagents. This does not usually matter to most chemists as we often want to carry out reactions in organic solvents rather than water. The reaction scheme is easy enough to draw, but what is the mechanism? But there is a problem! Carbon atoms that carry a negative charge, for example Me—, are known as carbanions.

But at this stage we just want you to appreciate that even the relatively simple chemistry in this chapter is useful in synthesis, in commerce, and in medicine.

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7.AN a aldeídos e cetonas QUI02015 3

The second reason that bisulfite compounds are useful is that they are soluble in water. Dapsone is an antileprosy drug. Aldehydes and ketones react with primary amines and ammonia to yield imines They react with secondary amines to yield enamines.

Reaction of triphenylphosphine with a primary or secondary alkyl halide produces a phosphonium salt The phosphonium salt is deprotonated by a strong base to form the ylide. The details of this sort of chemistry will come in Chapter 14 when you will meet imines as intermediates.

The ether solvent is essential cetknas Grignard formation because 1 ethers unlike, say, alcohols or dichloromethane will not react with Grignards and, more impor- tantly, 2 only in ethers are Grignard reagents soluble. Enviado por Karine flag Denunciar. The same arguments hold for the C—Mg bond of Grignard reagents.

Cetonad can be accomplished by adding a small amount of iodine or 1,2-diiodoethane, or by using ultra- sound to dislodge the oxide layer. The compound is commercially available and, together with the related zinc salt, is widely used in the textile industry as a reduc- ing agent. Mild acid facilitates departure of the hydroxyl group from the aminoalcohol intermediate without also protonating the nitrogen of the amine starting co mpound.

Aldeídos e cetonas

Similar glucosides are found in apple pips and the kernels inside the stones of fruit such as peaches and apricots. An aldehyde or ketone in the presence of excess alcohol and an acid catalyst will form an acetal. Some diseases found in eastern Nigeria can be traced to long-term consumption of HCN. How to make organolithium reagents Organolithium compounds may be made by a similar cetomas insertion reaction from lithium metal and alkyl halides.

Earlier in this chapter we mentioned the difficulty of working with formaldehyde because it is either an aqueous solution or a dry polymer.