Organic Chemistry 2nd Edition solutions

Organic Chemistry 2
Acid-catalyzed hydration of 1-methylcyclohexene yields two alcohols. The major product does not undergo oxidation, while the minor product will undergo oxidation. Explain.

Organic Chemistry 2
Draw a bond-line structure for each of the following compounds: (a) C C C H H H H H H H C H H C C H H H C H H H C H H H (b) O H C H C H H H C H H C C H H H (c) OH HO C OH C C H H H H H (d) (CH3)3C!C(CH3)3 (e) CH3CH2CH(CH3)2 (f) (CH3CH2)3COH (g) (CH3)2CHCH2OH (h) CH3CH2CH2OCH3 (i) (CH3CH2)2CRCH2 (j) C

Organic Chemistry 2
Predict the products obtained when 1-pentyne reacts with each of the following reagents: (a) H2SO4, H2O, HgSO4 (b) 9-BBN followed by H2O2, NaOH (c) Two equivalents of HBr (d) One equivalent of HCl (e) Two equivalents of Br2 in CCl4 (f) NaNH2 in NH3 followed by MeI (g) H2, Pt

Organic Chemistry 2
Draw a bond-line structure for each of the following compounds: (a) \(CH_2=CHCH_2C(CH_3)_3\) (b) \((CH_3CH_2)_2CHCH_2CH_2OH\) (c) \(CH\equiv COCH_2CH(CH_3)_2\) (d) \(CH_3CH_2OCH_2CH_2OCH_2CH_3\) (e) \((CH_3CH_2)_3CBr\) (

Organic Chemistry 2
The most stable conformation of 5-hydroxy-1,3-dioxane has the OH group in an axial position, rather than an equatorial position. Provide an explanation for this observation.

Organic Chemistry 2
Identify the stronger nucleophile: (a) \(\mathrm{NaSH}\) vs. \(\mathrm{H}_{2} \mathrm{~S}\) (c) Methoxide dissolved in (b) Sodium hydroxide vs. methanol vs. methoxide diswater solved in DMSO

Organic Chemistry 2
How many different alkenes will be produced when each of the following substrates is treated with a strong base? (a) 1-Chloropentane (b) 2-Chloropentane (c) 3-Chloropentane (d) 2-Chloro-2- methylpentane (e) 3-Chloro-3-methylhexane

Organic Chemistry 2
Triphenylmethane readily undergoes autooxidation to produce a hydroperoxide: Triphenylmethane (a) Draw the expected hydroperoxide. (b) Explain why triphenylmethane is so susceptible to autooxidation. (c) In the presence of phenol (C6H5OH), triphenylmethane undergoes autooxidation at a much slower rat

Organic Chemistry 2
When 2-methylpropane is treated with bromine in the presence of UV light, one product predominates. (a) Identify the structure of the product. (b) Draw the structure of the expected minor product. (c) Draw a mechanism for formation of the major product. (d) Draw a mechanism for formation of the minor

Organic Chemistry 2
Predict the major product of the reaction between 1-butanol and: (a) PBr3 (b) SOCl2, py (c) HCl, ZnCl2 (d) Conc. H2SO4, heat (e) PCC, CH2Cl2 (f) Na2Cr2O7, H2SO4, H2O (g) Li (h) NaH (i) TMSCl, Et3N (j) TsCl, pyridine (k) Na (l) Potassium tert-butoxide

Organic Chemistry 2
Draw structures for all constitutional isomers with the following molecular formulas: (a) \(\mathrm{C}_{2} \mathrm{H}_{6} \mathrm{O}\) (b) \(\mathrm{C}_{2} \mathrm{H}_{6} \mathrm{O}_{2}\) (c) \(\mathrm{C}_{2} \mathrm{H}_{4} \mathrm{Br}_{2}\)

Organic Chemistry 2
Malonic acid has two acidic protons: OH O HO O Malonic acid The pKa of the first proton (pK1) is measured to be 2.8, while the pKa of the second proton (pK2) is measured to be 5.7. (a) Explain why the first proton is more acidic than acetic acid (pKa=4.76). (b) Explain why the second proton is less a

Organic Chemistry 2
Calculate the HDI for each molecular formula. (a) C4H6 (b) C5H8 (c) C40H78 (d) C72H74 (e) C6H6O2 (f) C7H9NO2 (g) C8H10N2O (h) C5H7Cl3 ( i ) C6H5Br (j) C6H12O6

Organic Chemistry 2
Phenalamide A2 belongs to a class of natural products that are of interest because of their antibiotic, antifungal, and antiviral activity. In the first total synthesis of this compound, the following boronate ester was utilized (Org. Lett. 1999, 1, 17131715): O C O C C C C C B C O C C O H3C CH3 CH3

Organic Chemistry 2
Treatment of catechol with formaldehyde in the presence of an acid catalyst produces a compound with molecular formula C7H6O2. Draw the structure of this product. OH OH Catechol

Organic Chemistry 2
When 1,4-dioxane is heated in the presence of HI, compound A is obtained: O O Compound A 2 H2O Heat HI Excess + (a) Draw the structure of compound A. (b) If one mole of dioxane is used, how many moles of compound A are formed? (c) Show a plausible mechanism for the conversion of dioxane into compound

Organic Chemistry 2
There are only four constitutional isomers with molecular formula C4H9NO2 that contain a nitro group (!NO2). Three of these isomers have similar pKa values, while the fourth isomer has a much higher pKa value. Draw all four isomers and identify which one has the higher pKa. Explain your choice.

Organic Chemistry 2
Predict the bond angles for all bonds in the following compounds: (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) (b) \(\mathrm{CH}_{2} \mathrm{O}\) (c) \(\mathrm{C}_{2} \mathrm{H}_{4}\) (d) \(\mathrm{C}_{2} \mathrm{H}_{2}\) (e) \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) (f) \(\mathrm{CH}_{3

Organic Chemistry 2
Compound A has molecular formula C8H8O. An IR spectrum of compound A exhibits a signal at 1680 cm-1 . The 1 H NMR spectrum of compound A exhibits a group of signals between 7.5 and 8 ppm (with a combined integration of 5) and one upfield signal with an integration of 3. Compound A is converted into c

Organic Chemistry 2
Predict the major product(s) formed when hexanoyl chloride is treated with each of the following reagents: (a) CH3CH2NH2 (excess) (b) LAH (excess), followed by H2O (c) CH3CH2OH, pyridine (d) H2O, pyridine (e) C6H5CO2Na (f) NH3 (excess) (g) Et2CuLi (h) EtMgBr (excess), followed by H2O