f) Briefly explain why the amine shown below can only be isolated as a racemic m

Question

f) Briefly explain why the amine shown below can only be isolated as a racemic mixture of the R- and S-enantiomers while the ammonium bromide exists only as the S-enantiomer g) What would be the decreasing order of reactivity of the following carbonyl compounds towards nucleophilic reagents? (most reactive to least reactive) H3C CH i >ii >iii > iv iii>ii >iv ii > iv >i>ii h) Which compound of formula CsHiN is expected to have the lowest boiling point CH N, i) Which of the sulfonamides would be soluble in aqueous KOH solution? i) Which compound is a hemi-acetal? OH

Explanation / Answer

f) Tertiary amine with lone pair of electrons undergo rapid interconversion between two enantiomeric forms hence it exists in both R and S- enantiomers while its ammonium salt is non-interconvertible and rigid hence can be isolated as pure enantiomer

g) Answer: iv > iii > i > ii

This can be explained based on steric factors. Generally, aldehydes are more reactive than ketones due to electronic and steric factors and in ketones reactivity decreases with the bulkiness of alkyl groups around carbonyl carbon

h) Answer: 2

Tertiary amines generally have lower boiling points due to lack of H-bonding

i) Answer: 1

Sulfonamide 1 has an acidic hydrogen hence it reacts with KOH and form salt. The salt form is readily soluble in aqueous solution of KOH

j) Answer:2

COmpound 2 is a hemi-acetal that is formed between an aldehyde and alcohol

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