omework - Chapter 14 Chem 2320 Name 1. Label each alcohol in the the following compounds as primary, secondary, tertiary, enol, or aryl. 2. Fill in the blanks in the following sentences. Enols are in equilibrium with their or form. Compounds which contain a C-S- bonding sequence are called. The alcohol which can cause blindness if ingested is. An aryl alcohol may also be referred to as a. An alcohol containing a C=C in any location is referred to as a(n) alcohol. The oxygen in an alcohol always has an hybridization. g) The most common characteristic of thiols is their. h) Isopropanol is often used for. i) An aromatic alcohol is one containing a(n). j) The alcohol in alcoholic drinks is called. k) An enol must have. l) Alcohols with or are usually soluble in water. m) When an alcohol reacts with a base, a(n) is formed. n) When an alcohol reacts with an acid, a(n) is formed.
W Ch 14 p 2 3. Match up the following compounds with the spectra shown below. Label ALL important bands! A B C D
4. Match up the following alcohols with the formula C 6 14 with the 1 NMR data given below. Sketch each spectrum, and match up the peaks with 's in the structure of the compound you have chosen. Not all compounds will be used! W Ch 14 p 3 2-ethyl-1-butanol 3,3-dimethyl-1-butanol 2-methyl-1-pentanol 4-methyl-1-pentanol 4-methyl-2-pentanol 3-methyl-1-pentanol 3-methyl-2-pentanol 1-hexanol 2-hexanol 3-hexanol a - 0.8 ppm, 3, t b - 0.9 ppm, 3, d c - 1.2 ppm, 2, quint d - 1.6 ppm, 1, m(8) e - 1.9 ppm, 2, q f - 2.7 ppm, 1, bs g - 3.7 ppm, 2, t a - 0.9 ppm, 9, s b - 1.7 ppm, 2, t c - 2.5 ppm, 1, bs d - 3.7 ppm, 2, t a - 1.0 ppm, 3, t b - 1.1 ppm, 3, d c - 1.2 ppm, 2, m(6) d - 1.4 ppm, 2, quint e - 1.6 ppm, 2, q f - 3.1 ppm, 1, bs g - 3.7 ppm, 1, m(6) a - 0.9 ppm, 6, d b - 1.4 ppm, 2, q c - 1.6 ppm, 1, m(9) d - 1.9 ppm, 2, quint e - 2.2 ppm, 1, bs f - 3.6 ppm, 2, t a - 0.9 ppm, 6, t b - 1.3 ppm, 4, quint c - 1.8 ppm, 1, bs d - 2.2 ppm, 1, m(7) e - 3.4 ppm, 2, d a - 0.9 ppm, 3, t b - 1.1 ppm, 3, t c - 1.3 ppm, 2, m(6) d - 1.8 ppm, 2, q e - 1.9 ppm, 2, quint f - 2.1 ppm, 1, bs g - 3.6 ppm, 1, quint
W Ch 14 p 4 5. Circle the compound in each pair which has the higher boiling point, and briefly explain why. F 6. Circle the compound in each pair which is more acidic. Then give a brief explanation of why. S g)
h) water rubbing alcohol W Ch 14 p 5 i) j) 2 7. Give all products of the following acid-base reactions. Then indicate whether products or reactants (or neither) are favored by the equilibrium. Na Na Na 2 S 4 3 Na g) 2 2 h) 2 2 K i) 2 j) S Na
W Ch 14 p 6 8. Draw structures for the following alcohols. butyl alcohol allyl alcohol sec-butyl alcohol isopropyl alcohol tert-butyl alcohol benzyl alcohol 9. Name the following compounds.
W Ch 14 p 7 g) h) Br i) j) k) l) 10. Draw structures for the following compounds. dicyclopropylmethanol 1-cyclobutyl-4-penten-2-ol trans-4-(2-butenyl)-3-isopropyl-1-cyclohexanol (S)-1-penten-4-yn-3-ol 3-(3-hydroxypropyl)-1-cyclopentanol 3-chloro-4-(1-hydroxyethyl)-2-isopropyl-2-cyclobuten-1-ol
W Ch 14 p 8 11. Give reagents which would convert the following compounds to the alcohol shown. g) Br h) i)
W Ch 14 p 9 12. Indicate whether the following transformations represent an oxidation or reduction and explain why. N N 2 N 2 N 2 g) h) j) N N k) l) S S
W Ch 14 p 10 13. Give the products of the following reactions. NaB 4 C 3 NaB 4 1. Al 4 2. 3 1. Al 4 2. 3 NaB 4 C 3 1. Al 4 2. 3 g) NaB 4 h) 1. Al 4 2. 3 i) NaB 4 C 3 j) 2, Pd/C j) Raney Ni
W Ch 14 p 11 14. Label the dipole in the following molecules. Br MgBr 15. Give starting materials and reagents to show how the following organometallic reagents could be formed. MgBr Mg MgI MgBr g) h)
W Ch 14 p 12 16. Give ALL of the products of the following reactions. Draw arrows to show how the reaction takes place. MgBr Mg D D MgI 3 C 17. Give the products of the following reactions. Draw arrows to show how the reaction occurs. Mg MgBr
W Ch 14 p 13 18. Show the mechanism by which the following products were formed, including all steps, arrows, electron pairs, and formal charges! 2 2. 3 Mg Mg 2 2 1. 2 eq 3 C 2. 3 2 2 2 Mg 2. 3 Mg 2-2 19. Give the final product of the following reactions. 1. C 3 MgBr 2. 3 b 1. formaldehyde 2. 3
W Ch 14 p 14 Mg 2. 3 1. 2. 3 2 MgBr 2. 3 2 2. 3 g) Mg 2. 3 h) 2 2. 3 i) 2 2. 3 j) MgBr 2. 3 k) MgBr 2 2. 3 l) 2. 3 m) MgI 1. 2 2. 3
W Ch 14 p 15 20. Show all reagents that would be necessary to perform the following reactions. If more than one arrow is written, it means that there is more than one step. C 3 Br 2 g) h) i) j)
W Ch 14 p 16 k) l) m) Br n) o) Br p) q) r) s) 2 I t) u) 2 Br