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Module 7: Organic Chemistry

Quick questions on Amines and amides explained: HSC Chemistry Module 7

15short Q&A pairs drawn directly from our worked dot-point answer. For full context and worked exam questions, read the parent dot-point page.

What is amines?
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An amine has a nitrogen with at least one $N-H$ or $N-C$ bond and no carbonyl on that nitrogen. Classify by counting how many carbons are bonded to the nitrogen.
What is amides?
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An amide has a nitrogen directly attached to a carbonyl carbon: $R-CO-NR'R''$. Classify by counting how many carbons are on the nitrogen (the same as amines, ignoring the carbonyl-attached carbon for classification purposes in many texts; HSC convention varies, but the safe call is to say "primary amide has $-CONH_2$, secondary has $-CONHR$, tertiary has $-CONR_2$").
What is physical properties?
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Boiling points. Amines with $N-H$ bonds hydrogen-bond, so primary and secondary amines boil above hydrocarbons of similar molar mass. Tertiary amines have no $N-H$ and cannot donate hydrogen bonds (though they can accept), so they boil lower than primary/secondary amines.
What is amines as weak bases?
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The lone pair on nitrogen can accept a proton, making amines bases (analogous to ammonia):
What is formation of amines?
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The HSC scope includes two pathways:
What is formation of amides?
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An amide forms by condensation of a carboxylic acid with ammonia or an amine. The initial salt loses water on heating:
What is amides in polymers?
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The amide linkage is the repeating unit in polyamides such as nylon 6,6 (made from 1,6-diaminohexane and hexanedioic acid) and proteins (made from amino acids). See the polymers dot point for full equations.
What is naming?
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For a primary amine, name as alkanamine with a locant for the nitrogen-bearing carbon. For secondary and tertiary, name the parent amine after the longest chain and use $N-$ locants for the other substituents.
What is boiling points?
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Amines with $N-H$ bonds hydrogen-bond, so primary and secondary amines boil above hydrocarbons of similar molar mass. Tertiary amines have no $N-H$ and cannot donate hydrogen bonds (though they can accept), so they boil lower than primary/secondary amines.
What is solubility?
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Small amines (up to about C4) are very soluble in water through hydrogen bonding. Aliphatic amines have a characteristic ammonia-like or fishy smell. Decaying flesh produces low-molar-mass amines such as putrescine ($H_2N(CH_2)_4NH_2$) and cadaverine ($H_2N(CH_2)_5NH_2$), responsible for the smell.
What is confusing amine and amide classifications?
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Amine: $-NH_2$, no adjacent carbonyl. Amide: $-CONH_2$ or $-CONR_2$, has a carbonyl. The two are not interchangeable.
What is comparing amine basicity with alcohol?
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Amines are weak bases; alcohols are essentially neutral. Mention the lone pair on nitrogen.
What is forgetting the loss of water in amide formation?
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The condensation releases water, just like esterification. Without that, your equation is unbalanced.
What is claiming tertiary amines hydrogen bond as donors?
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They have no N-H, so they cannot donate. They can still accept hydrogen bonds via the nitrogen lone pair.
What is drawing an N-H on a tertiary amine?
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A tertiary amine has three carbons on N and zero hydrogens.

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