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Organic Chemistry — Practice Questions flashcards

6 of 55 questions free to study here · 24 topics · the whole deck is built into Willys

Multiple-choice practice questions, one best answer each, on naming and stereochemistry, substitution and elimination, additions, carbonyl and aromatic chemistry, and spectroscopy.

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Practice 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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  1. Four compounds have molar masses of about 72 to 74 g/mol. Which has the highest boiling point?

    A) 1-Butanol
    B) Pentane
    C) Butanal
    D) Diethyl ether
    A) 1-Butanol

    Only 1-butanol has an O–H group, so its molecules hydrogen-bond to one another. Butanal has a polar C=O and dipole–dipole attraction but no O–H to donate, so it boils far lower; the ether and pentane are lower still.
    Polarity & Intermolecular Forces
  2. How many stereoisomers exist for pentane-2,4-diol, CH₃CH(OH)CH₂CH(OH)CH₃?

    A) 4
    B) 3
    C) 8
    D) 2
    B) 3

    There are two stereocenters, so up to 2² = 4, but C2 and C4 carry identical sets of groups. The (2R,4S) form has an internal mirror plane and is meso, leaving one pair of enantiomers plus the meso compound: 3.
    Stereoisomers
  3. 2-Bromo-3-methylbutane is heated with sodium ethoxide in ethanol. What is the major product?

    A) 2-Methylbut-1-ene
    B) 3-Methylbut-1-ene
    C) 2-Methylbut-2-ene
    D) 2-Ethoxy-3-methylbutane
    C) 2-Methylbut-2-ene

    A small strong base gives E2 elimination that follows Zaitsev's rule: losing the C3 hydrogen forms the trisubstituted alkene, favored over 3-methylbut-1-ene, the monosubstituted alkene from a C1 hydrogen. 2-Methylbut-1-ene cannot form without rearrangement, and a secondary halide with a strong base mostly eliminates rather than giving the ether.
    E2 Elimination
  4. Rank these carbonyl compounds by reactivity toward nucleophilic addition, most reactive first.

    A) Acetaldehyde > acetone > formaldehyde
    B) Formaldehyde > acetaldehyde > acetone
    C) Acetone > acetaldehyde > formaldehyde
    D) Acetaldehyde > formaldehyde > acetone
    B) Formaldehyde > acetaldehyde > acetone

    Each alkyl group on the carbonyl carbon donates electron density and adds steric bulk, making the carbon less electrophilic and harder to reach. Formaldehyde has none, acetaldehyde one and acetone two.
    Carbonyl Reactivity
  5. Which conversion proceeds readily at room temperature with no activating reagent?

    A) Sodium acetate + ethanol → ethyl acetate
    B) Ethyl acetate + NaCl → acetyl chloride
    C) Acetyl chloride + methanol → methyl acetate
    D) Acetamide + ethanol → ethyl acetate
    C) Acetyl chloride + methanol → methyl acetate

    Acyl substitution runs easily downhill: acyl chloride > anhydride > ester > amide > carboxylate. Making an ester from the acyl chloride is downhill; the other three try to climb to a more reactive derivative.
    Carboxylic Acid Derivatives
  6. A mass spectrum shows a molecular ion at m/z 122 and an M + 2 peak at m/z 124 of nearly equal height. Which compound fits?

    A) 1-Chlorobutane
    B) 1-Iodopropane
    C) Benzoic acid
    D) 1-Bromopropane
    D) 1-Bromopropane

    Peaks of nearly equal height two units apart are the signature of one bromine (⁷⁹Br and ⁸¹Br, about 1 : 1), and C₃H₇⁷⁹Br has mass 122. Benzoic acid also has M = 122 but no large M + 2 peak, and a chlorine would give a 3 : 1 pattern.
    ¹³C NMR & Mass Spectrometry

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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., Pavia et al., Introduction to Spectroscopy, and IUPAC Nomenclature of Organic Chemistry (2013 Recommendations) — reference only; no text copied.
  • Original questions written for this deck; no exam, textbook or question-bank items were copied.

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