ACS Exam Organic Chem Questions and Answers Graded A 2024

O-H and N-H IR shift - 3400 cm⁻¹ C-H SP³ IR shift - cm⁻¹ C-H SP₂ IR shift - cm⁻¹ C-H SP IR Shift - 3300 cm⁻¹ 3x bond C-C IR shift - 2100 cm⁻¹ C=O IR shift - 1700 cm⁻¹ C=C and C-C aromatic IR shift - 1600 cm⁻¹ Aromatic C-C IR shift - 1500 cm⁻¹ HNMR shift of methyl hydrogen - 1 ppm HNMR shift of hydrogen attached to SP2 carbon - 2 ppm HNMR shift of aromatic hydrogen - 7-8 ppm HNMR shift of hydrogen attached to SP3 carbon attached to a pi system - 5-6 ppm HNMR shift of aldehyde proton - 10 ppm HNMR shift of carboxylic acid proton - 11-12 ppm CNMR shift of SP₃ alkyl carbon - 10-30ppm CNMR shift of SP₃ C attached to O, N or halogen - 50-70 ppm CNMR shift of SP Carbon - 75-90 ppm CNMR shift of SP₂ carbon (double bond or aromatic carbon) - 100-150 ppm CNMR shift of ester, amide or carboxyl carbon c=o - 160-180 ppm CNMR shift of aldehyde or ketone carbon c=o - 190-200 ppm NaH and an alcohol - NAH deprotonates alcohol to yield alkoxide ion Alcohol and metal (Li, Na, K) - Deprotonation of alcohol to yield alkoxide ion alkyl halide (primary) and NaOH - Primary alcohol Tertiary alkyl halide and water - Tertiary alcohol Alkene and dilute H₂SO₄ - Alcohol, markovnikov addition Alkene and Hg(OAc)₂, H₂O followed by NaBH₄ - Alcohol, oxymercuration demercuration (markovnikov) Alkene and BH₃, THF followed by H₂O₂, NaOH - Alcohol, anti-markovnikov via hydroboration oxidation LAH and NaBH₄ reagents - both reducing, but LAH able to reduce esters and carboxylic acids as well Ketone and NaBH₄ - Alcohol Ester and NaBH₄ - No reaction; NaBH₄ not strong enough Ketone and grignard reagent - Yields alcohol with new R group Aldehyde and grignard reagent - Yields alcohol with new R group xs Grignard reagent and ester - Alcohol with two new R groups Grignard reagent and carboxylic acid - No alcohol! cant use grignard in presence of OH Alcohol and TMSCl - Protects alcohol by turning OH into OTMS Deprotect alcohol using - TBAF Primary and H-Br - Alkyl bromide Primary alcohol and ZnCl₂ - Alkyl chloride