Organic Chemistry Reaction

[SyrianHero]

What is the process that I should go through to solve a question like question 45 in the AMCAS practice test: Although highly toxic, amygdalin has been investigated as a potential anti-cancer compound. When refluxed in H2SO4(aq), amygdalin breaks down to produce glucose (2 equivalents), HCN (1 equivalent), and benzaldehyde (C6H5CHO, 1 equivalent). Which structure most likely corresponds to amygdalin? (I wasn't able to paste the answers here).

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[ofi2016]

bump, i have the same question!

 

[a_borgia]

I think I remember this questions - first check that all components are there (2 glucose, HCN, benzaldehyde). Then check that the bonds between them can be broken by sulferic acid - there was only one like that for me. If you can PM me the answers I can explain better.

 

[EverStriving]

H2SO4 is a strong Bronsted acid, meaning it forces protons onto nucleophilic groups, making them better leaving groups. Water can then come in and replace the protonated leaving group, hydrolyzing the bond. So look for the answer that contains 2 glucose, 1 nitrile group, and 1 benzaldehyde-like portion, connected by bonds that can be hydrolyzed by acid. There is only one answer that fits this criterion.

 

[BerkReviewTeach]

This is a carbonyl chemistry question with a carbohydrate application. Questions like this test your knowledge of linkages from an organic chemistry perspective. Try looking back at ketals and acetals in organic chemistry and note that they can be hydrolyzed in acidic water, but not basic water. With this in mind, add water across every connection (linkage) in each answer choice and see which choice gives the four compounds listed in the question. What you should notice is that one choice will lack the C for benzaldehyde (or something like that), another has a link that cannot be hydrolyzed, and so on. Only one will remain standing after process of elimination.

 

[deleted612812]