Hydration of alkynes (via oxymercuration) gives good yields of single compounds only with symmetrical or terminal alkynes. Show what the products would be from hydration of each compound.

e. 3-methylcyclodecyne

Which of the following compounds would give a positive Tollens test? (Remember that the Tollens test involves mild basic aqueous conditions.)

(a) CH₃CH₂CH₂COCH₃

(b) CH₃CH₂CH₂CH₂CHO

(c) CH₃CH=CHCH=CHOH

Which of the following compounds would give a positive Tollens test? (Remember that the Tollens test involves mild basic aqueous conditions.)

(d) CH₃CH₂CH₂CH₂CH(OH)OCH₃

(e) CH₃CH₂CH₂CH₂CH(OCH₃)₂

(f)

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

Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions.

(a)

Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions.

(b)

Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions.

(c)

One of these reacts with dilute aqueous acid and the other does not. Give a mechanism for the one that reacts, and show why this mechanism does not work for the other one.

(a)

One of these reacts with dilute aqueous acid and the other does not. Give a mechanism for the one that reacts, and show why this mechanism does not work for the other one.

(b)

Show a complete mechanism for this equilibrium established in diethyl ether with HCl gas as catalyst.

Show a complete mechanism for this reaction.

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.

Simple aminoacetals hydrolyze quickly and easily in dilute acid. Propose a mechanism for hydrolysis of the following aminoacetal: