Question

Give the structure of a compound that satisfies each of the following criteria (parts a through e). (a) A compound C 3

​
H 5
​
N that liberates ammonia on (b) A compound C 3
​
H 7
​
ON that liberates ammonia on treatment with hot aqueous KOH. treatment with hot aqueous KOH. (c) A compound that gives 1-butanol and (d) A compound that gives equal amounts of 1-hexanol 2-methyl-2-propanol on treatment with excess CH 3
​
MgI and 2-hexanol on treatment with LiAlH 4
​
followed followed by protonation. by protonation. (e) A compound C 3
​
H 2
​
N 2
​
that gives CO 2
​
, +
NH 4
​
, and acetic acid after boiling in concentrated aqueous HCl.

Answer 1

This chemistry question requires identification of compounds based on their chemical reactions and is typically suited for high school students studying organic chemistry, stoichiometry, and acid-base reactions.

Step-by-step explanation:

The question entails identifying chemical compounds based on specific reactions and criteria provided. It covers various concepts such as organic chemistry nomenclature and reactions, stoichiometry, and thermochemistry.

Compounds that fit the given criteria can be complex, as in the case of creating ammonia, the details of which extend beyond basic chemistry concepts. For example, the breakdown of compounds to liberate ammonia on treatment with hot aqueous KOH is a characteristic reaction of amides.

Furthermore, when discussing compounds that on certain treatments give products like alcohols, we are considering reductions and organometallic addition reactions.

Lastly, regarding Brønsted-Lowry acids and bases, we must identify strong acids and bases, such as HCl and NaOH, respectively, and those with intermediate strengths, like NH3 which can act as a base, and CH3CO₂H which can behave as a weak acid.

Answer 2

The specified compounds are aziridine (a), ethyl carbamate (b), diethyl ether (c), 3-hexanone (d), and azodicarbonamide (e), each satisfying the given chemical criteria and reactions.

Step-by-step explanation:

The student's question deals with identifying compounds based on specified chemical criteria. Here are the answers:

• (a) A compound with the formula C3H5N that liberates ammonia upon treatment with hot aqueous KOH could be an aziridine, which on hydrolysis would generate ethylenediamine and ammonia.
• (b) A compound with the formula C3H7NO that liberates ammonia under the same conditions could be ethyl carbamate, which on hydrolysis would yield ethanol and ammonia.
• (c) The compound that gives 1-butanol upon treatment with excess CH3MgI followed by protonation is diethyl ether. The Grignard reagent would add twice, leading to two butanol molecules upon workup.
• (d) A compound giving equal amounts of 1-hexanol and 2-hexanol upon treatment with LiAlH4 could be 3-hexanone, which would be reduced to a mixture of the two alcohols.
• (e) For C3H2N2 giving CO2, NH4+, and acetic acid after boiling in concentrated aqueous HCl, this could be azodicarbonamide, which can release these products upon decomposition.