Chapter 18: Q25. (page 950)
Propose a mechanism for the acid-catalyzed hydrolysis of cyclohexanone dimethyl acetal.
Short Answer
Dilute aqueous acid can be used for the hydrolysis of cyclohexanone dimethyl acetal. The mechanism is shown below.

/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none}
Learning Materials
Features
Discover
Chapter 18: Q25. (page 950)
Propose a mechanism for the acid-catalyzed hydrolysis of cyclohexanone dimethyl acetal.
Dilute aqueous acid can be used for the hydrolysis of cyclohexanone dimethyl acetal. The mechanism is shown below.

All the tools & learning materials you need for study success - in one app.
Get started for free
Predict the products formed when cyclopentanone reacts with the following reagents.
(a) CH3NH2 , H+
(b) excess CH3OH , H+
(c) hydroxylamine and weak acid
(d) ethylene glycol and p-toluenesulfuric acid
(e) phenylhydrazine and weak acid
(f) PhMgBr and then mild H3O+
(g) Tollens reagent
(h) sodium acetlylide, then H3O+
(i) hydrazine, then hot. fused KOH
(j) Ph3P=CH2
(k) sodium cyanide
(l) acidic hydrolysis of the product from (k)
In the mechanism for acetal hydrolysis shown, the ring oxygen atom was protonated first, the ring was cleaved, and then the methoxy group was lost. The mechanism could also be written to show the methoxy oxygen protonating and cleaving first, followed by ring cleavage. Draw the alternative mechanism.
(a) Simple aminoacetals hydrolyze quickly and easily in dilute acid. Propose a mechanism for hydrolysis of the following aminoacetal:

(b) The nucleosides that make up DNA have heterocyclic rings linked to deoxyribose by an aminoacetal functional group. Point out the aminoacetal linkages in deoxycytidine and deoxyadenosine.

(c) The stability of our genetic code depends on the stability of DNA. We are fortunate that the aminoacetal linkages of DNA are not easily cleaved. Show why your mechanism for part (a) does not work so well with deoxycytidine and deoxyadenosine.
Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.

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

(c)

(d)

(e)

(f)

(g)

What do you think about this solution?
We value your feedback to improve our textbook solutions.