Organic Chemistry I

Use this for “A compound is C₅H₇N. How many rings and π bonds can it have?”

Use this for “Does hydroxide take the proton from phenol (pKₐ 9.95)? Water’s pKₐ is 15.7. Find K.”

Use this for “Name HOCH₂CH₂COOH. Which group gives the ending, and which becomes a prefix?”

Use this for “Rank phenol, water, ethyne and ammonia from the strongest acid to the weakest.”

Use this for “A solution of butan-2-ol (0.100 g/mL) rotates light +0.945° in a 1.00 dm tube. Pure (S)-butan-2-ol has [α] = +13.5°. Find the ee.”

Use this for “A methyl group’s A-value is 7.3 kJ/mol. What percent of methylcyclohexane molecules hold the methyl equatorial at 298.15 K?”

Use this for “Rank –CH₃, –OH, –H and –CH₂OH by Cahn–Ingold–Prelog priority, highest first.”

Use this for “In an SN2 reaction [RX] is halved and [Nu] is made 4 times larger. How does the rate change?”

Use this for “Step 1 climbs 85 kJ/mol to a cation at 50 kJ/mol; step 2 climbs 15 more and ends at −30. Which step is slow, and what is ΔH?”

Use this for “Rank 2-bromopropane, bromomethane and bromoethane by how fast each reacts with iodide in acetone.”

Use this for “0.750 g of C₁₀H₁₆ (136.24 g/mol) takes up 11.01 mmol of H₂ over Pd. How many rings and π bonds?”

Use this for “cis-But-2-ene reacts with Br₂. Is the product meso or a pair of enantiomers?”

Use this for “A CH₂ next to a CH₃ shows J = 6.8 Hz at 300 MHz. How many lines, how wide is it in Hz and ppm, and what is δ for 1110 Hz from TMS?”

Use this for “A spectrum has a strong, sharp band at 1720 cm⁻¹ and nothing above 3000. Which functional group is it?”

Use this for “What is the exact mass of C₇H₈O, and how many ppm off is a peak measured at m/z 108.0573?”

Use this for “A compound shows peaks at m/z 136 and 138 with heights 100 and 97. Which halogen does it hold?”

Use this for “2,2-Dimethyloxirane reacts with NaOCH₃ in CH₃OH. Which ring carbon does the methoxide bond to?”

Use this for “Plan a synthesis of tert-butyl methyl ether, (CH₃)₃COCH₃, from an alcohol and an alkyl halide.”

Use this for “For CH₄ + Br₂, take C–H 439, H–Br 366, Br–Br 193 and C–Br 293 kJ/mol. Find ΔH of each propagation step and overall.”

Use this for “Put the steps of the light-driven chlorination of methane in order, from initiation to termination.”