10 Naming & structure practice bank

Cover the answer, work it out, then reveal. Add your own with the data file.

Name → structure

Draw/condense: 2-methylbutan-2-ol Reveal (CH₃)₂C(OH)CH₂CH₃. A tertiary alcohol (the C–OH carbon has three C neighbours). Condense: 3-chloro-2-methylpentane Reveal CH₃CH(CH₃)CH(Cl)CH₂CH₃ Condense: methyl propanoate Reveal CH₃CH₂COOCH₃ (propanoic acid part + methyl from methanol). Condense: N/A. Draw but-2-ene showing why it has E/Z Reveal CH₃CH=CHCH₃. Each double-bond carbon carries a CH₃ and an H (two different groups), so cis (Z) and trans (E) forms exist.

Structure → name

Name: CH₃CH₂CH₂CHO Reveal butanal (aldehyde, –CHO on the end carbon = C1). Name: CH₃COCH₂CH₃ Reveal butanone (ketone; C=O on C2). Name: HOCH₂CH₂CH₂COOH Reveal 4-hydroxybutanoic acid (acid outranks alcohol → acid gets the suffix and C1). Name: CH₃CH(NH₂)COOH Reveal 2-aminopropanoic acid (this is alanine: acid suffix, amino prefix).

Predict the product

Propene + HBr → ? (main product + why) Reveal 2-bromopropane. Markovnikov: H adds to the terminal CH₂ (more H’s), Br to the middle C via the more stable secondary carbocation. Bromoethane + KCN in ethanol → ? Reveal Propanenitrile, CH₃CH₂CN (nucleophilic substitution; chain lengthened by one carbon). Butan-2-ol + K₂Cr₂O₇/H⁺, reflux → ? Reveal Butanone (a secondary alcohol oxidises to a ketone; no further oxidation). Ethyl ethanoate + NaOH(aq), reflux → ? Reveal Sodium ethanoate (CH₃COO⁻Na⁺) + ethanol (base hydrolysis).

Practice for this standard covers the whole topic — flashcards and quiz.