Propose a mechanism for each cyanohydrin synthesis just shown.

Short Answer

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The conjugate base of hydrogen cyanide (HCN) is cyanide ion (CN-) . Cyanide ion is considered to be a strong base as well as a strong nucleophile also. Cynaide ion can attack carbonyl compounds (aldehydes and ketones) to form an additional product which is more commonly known as the cyanohydrins

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01

Cyanohydrins

The conjugate base of hydrogen cyanide (HCN) is cyanide ion (CN-) . Cyanide ion is considered to be a strong base as well as a strong nucleophile also. Cynaide ion can attack carbonyl compounds (aldehydes and ketones) to form an additional product which is more commonly known as the cyanohydrins

02

Mechansim for the synthesis of each cyanohydrin

The formation of cyanohydrin is a type of base-catalyzed addition to a carbonyl group where a strong nucleophile (CN-) adds in the first step to give an alkoxide which on protonation in the second step forms the cyanohydrin.

(propanol) (propanol cyanohydrin)

(butane-2-one) (butane-2-one cyanohydrin)

(di-tert-butylketone)

Ketones hindered by the presence of large alkyl groups usually react very slowly with hydrogen cyanide and give poor yields of cyanohydrins. Poor yield is due to steric effects.

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Most popular questions from this chapter

NMR spectra for two compounds are given here, together with the molecular formulas. Each compound is a ketone or an aldehyde. In each case, show what characteristics of the spectrum imply the presence of a ketone or an aldehyde, and propose a structure for the compound.

Show how you would accomplish the following syntheses efficiently and in good yield. You may use any necessary reagents.

(a)acetaldehydelacticacid,CH3CH(OH)COOH

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The family of macrolide antibiotics all have large rings (macrocycle) in which an ester is what makes the ring; a cyclic ester is termed as a lactone. One example is amphotericin B, used as an anti-fungal treatment of last resort because of its liver and heart toxicity. Professor Martin Burke of the University of Illnois has been making analogs to retain the antifungal properties but without the toxicity, including this structure published in 2015. (Nature Chemical Biology, (2015) doi: 10.1038/nchembio.1821). The carboxylate of amphotericin B has been replaced with the urea group (shown in red).

(a) Where is the lactone group that forms the ring?

(b) Two groups are circled. What type of functional group are they? Explain.

Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.

a.

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Question: Solving the following road-map problem depends on determining the structure of A, the key intermediate. Give structures for compounds A through K.

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