Organic Chemistry — Carbonyls, Aromatics & Spectroscopy flashcards
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Carbonyl additions and acyl substitutions, acetals, imines, Wittig, hydride reductions, enolate chemistry from aldol to Robinson annulation, acid derivatives, amine basicity, aromaticity and electrophilic aromatic substitution, then IR, NMR, mass spec and UV–Vis.
Learn deck · part of Organic Chemistry I/II · written against: Standard two-semester sequence; compound names use either the traditional locant style (1-butene, 2-propanol) or the IUPAC 2013 style (but-1-ene, propan-2-ol), both in wide use, and the nomenclature cards teach the 2013 rule. Updated 2026-10-10.
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Which is more reactive toward nucleophilic addition, an aldehyde or a ketone, and for what two reasons?Aldehydes. Sterically, the lone R group leaves the carbonyl carbon more exposed; electronically, a ketone's second alkyl group donates electron density and reduces the carbon's partial positive charge. Formaldehyde, with no alkyl groups at all, is the most reactive of the family.Carbonyl Reactivity
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How does an aldehyde become an acetal with an alcohol, what conditions are required, and how is the reaction driven forward or backward?Under acid catalysis one alcohol adds to give the hemiacetal; protonation of its OH and loss of water gives an oxocarbenium ion, and a second alcohol adds to give the acetal. Remove water (a Dean–Stark trap) to drive it forward; aqueous acid runs it in reverse.Hydrates · Acetals & Protecting Groups
Watch out: acetals form only under acid, never under base. -
What does NaBH₄ reduce, and what does LiAlH₄ reduce that NaBH₄ cannot?NaBH₄ (mild, used in alcohol or water) reduces aldehydes and ketones to alcohols, reacts only very slowly with esters, and leaves acids and amides untouched. LiAlH₄ (powerful, dry ether, then aqueous workup) also reduces esters and acids to primary alcohols, amides to amines, and nitriles to primary amines.Reductions & Oxidations
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Roughly what are the α-hydrogen values of a ketone, an ester and a 1,3-diketone, and what explains the differences?Ketone about 19–20, ester about 25, 1,3-diketone about 9. The enolate's negative charge delocalizes onto the carbonyl oxygen; two carbonyls share it, making the dicarbonyl far more acidic, while an ester's alkoxy lone pair already donates into its carbonyl and weakens that stabilization.Enols & Enolates
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Rank the carboxylic acid derivatives by reactivity toward nucleophilic acyl substitution and explain the order.Acyl chloride > anhydride > ester > amide > carboxylate. Reactivity rises with a better (less basic) leaving group and falls as the heteroatom's lone pair donates more into the carbonyl. Going down the order is usually one direct step (an acyl chloride plus an alcohol gives an ester); going up needs activation.Carboxylic Acid Derivatives
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Rank ammonia, methylamine, aniline, pyridine and acetamide by basicity, and explain the order.Methylamine > ammonia > pyridine > aniline >> acetamide (conjugate-acid about 10.6, 9.2, 5.2, 4.6 and −1). Alkyl groups donate electron density; pyridine's sp² lone pair is held more tightly than an sp³ one; aniline's lone pair is delocalized into the ring and an amide's into the carbonyl.Amines
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What is the general mechanism of electrophilic aromatic substitution, and why is substitution favored over addition?The ring's π electrons attack the electrophile to give a resonance-stabilized cation, the arenium ion (sigma complex); a base then removes the proton from that carbon. Losing H⁺ restores aromaticity, whereas adding a nucleophile would forfeit it, so substitution wins.Electrophilic Aromatic Substitution
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Where does a C=O stretch appear in an IR spectrum, and how do the exact positions help identify esters, ketones, aldehydes, amides and acids?A strong, sharp band near 1700 cm⁻¹. Ester about 1735, ketone 1715, aldehyde 1725 (with two weak C–H bands near 2720 and 2820), amide 1650–1690; conjugation lowers each by about 30. A carboxylic acid pairs its 1710 band with a very broad O–H stretching from 2500 to 3300.IR Spectroscopy
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What are the main ¹³C NMR shift regions, and why do the peaks appear as singlets with unreliable heights?Carbonyl 160–220 ppm (ketones and aldehydes 190–220, acids, esters and amides 160–185); aromatic and alkene 100–160; C–O 50–90; alkyl 0–50. Spectra are run with broadband proton decoupling, so each unique carbon is a singlet; peak heights are not proportional to carbon counts because of differing relaxation.¹³C NMR & Mass Spectrometry
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How does extending conjugation change a compound's UV–Vis absorption, and why?Each extra conjugated double bond raises λmax (a red shift) because the HOMO–LUMO gap shrinks: ethylene absorbs near 165 nm, 1,3-butadiene at 217, 1,3,5-hexatriene at 258, and β-carotene with eleven conjugated C=C absorbs in the visible near 450 nm, which is why it looks orange.UV–Vis
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About these cards
Review status: Second-reader reviewed, with corrections applied.
Checked against:
- OpenStax Organic Chemistry: A Tenth Edition, consulted as a reference; no text copied.
- Checked against Clayden, Greeves & Warren, Organic Chemistry, 2nd ed. and Pavia et al., Introduction to Spectroscopy (reference only; no text copied).
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