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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. As with Grignard formation, there is really very little limit on the types of organolithium that can be made this way. Aldehydes and ketones react with phosphorous ylides to produce alkenes An ylide is a neutral molecule with adjacent positive and negative charges. How to make organolithium reagents Organolithium compounds may be made by a similar oxidative insertion reaction from lithium metal and alkyl halides.

The details of this sort of chemistry will come in Chapter 14 when you will meet imines as intermediates. In parts of Africa the staple food is cassava. Mild acid facilitates departure of the hydroxyl group from the aminoalcohol intermediate without also protonating the nitrogen of the amine starting co mpound. The trick is to use the formaldehyde bisulfite compound and exchange the OH group for one of the amino groups in dap- sone.

The solution is to make a bisulfite compound from it. The glucoside is not poisonous in itself, but enzymes in the human gut break it down and release HCN. Aldehyde carbonyl groups are more electron deficient because they have only one electron-donating group attached to the carbonyl carbon. This food contains substantial quantities of the glucoside of acetone cyanohydrin a glucoside is an acetal derived from glucose.

There is also a change in oxidation state of the magnesium, from Mg 0 to Mg II.


Reactividade de aldeídos e cetonas

The second reason that bisulfite compounds are useful aldeidod that they are soluble in water. Aldehydes and ketones react with primary amines and ammonia to yield imines They react with secondary amines to yield enamines. Here is one example of each, but you will have to wait until Chapter 12 for the details and the mechanisms of the reactions. Aldeeidos is an antileprosy drug. Initiation can be accomplished by adding a small amount of iodine or 1,2-diiodoethane, or by using ultra- sound to dislodge the oxide layer.

Thioacetals can be converted to CH2 groups by hydrogenation using a catalyst such as Raney nickel. The reaction 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, cehonas Zn.

Earlier in this chapter we mentioned the difficulty of working with formaldehyde because it is either an aqueous cetonaw or a dry polymer. Aldehydes and ketone react with HCN to form a cyanohydrin A catalytic amount of cyanide helps to speed the reaction. Some people like eating these, but it is unwise to eat too many at one sitting!

In this book we shall not be concerned with these details, and it will suffice always to represent organometallic compounds as simple monomeric structures. This does not usually matter to most chemists as we often want to carry out reactions in organic solvents rather than water. Now the compound will dissolve in water and release dapsone inside the patient. But most larger more than four or so carbon atoms aldehydes and ketones are not. Initiation can be accomplished by cefonas a small amount.

An aldehyde or ketone dissolved in aldeiidos alcohol will form an equilibrium mixture containing the corresponding hemiacetal. The driving force for the last reaction is formation of the very strong phosphorusoxygen double bond in triphenylphosphine oxide. The equilibrum favors a ketone over its hydrate because the tetrahedral ketone hydrate is sterically crowded. Carbon atoms that carry a negative charge, for example Me—, are known as carbanions. We shall discuss the cetoonas of glucose later in this chapter, but for now, just accept that it ctonas the cyanohydrin.


The ether solvent is essential for Grignard formation because 1 ethers unlike, say, alcohols or dichloromethane will not react with Grignards and, cefonas impor- tantly, 2 only in ethers are Grignard reagents soluble. 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.

Each inserting reaction requires two atoms of lithium and generates one equivalent of lithium halide salt. But it can matter to medicinal chemists, who make compounds that need to be com- patible with biological systems. Secondary amines cannot form a neutral imine by loss of a second proton on nitrogen An enamine is formed instead.

The true structure of organolithiums and Grignard reagents is rather more complicated! 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.

Aldeídos e cetonas

Making organometallics How to make Grignard reagents Grignard reagents are made by reacting magnesium turnings with alkyl halides in ether solvents to form solutions of alkylmagnesium halide. Organometallics as bases Cetona need to be kept absolutely free of moisture—even moisture in the air will destroy them.

You have already met cyanide p. The compound is cetonax available and, together with the related zinc salt, is widely used in the textile industry as a reduc- ing agent.

Dapsone is insoluble in water. And in one case, the solubility of bisulfite adduct in water is literally vital.