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Chapter 14 Organic Compounds That Contain Oxygen, Halogen, Or Sulfur

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Chapter 14–1 Chapter 14 Organic Compounds That Contain Oxygen, Halogen, or Sulfur Solutions to In-Chapter Problems 14.1 Label the –OH groups, –SH groups, halogens, and ether oxygens in each compound. b. The OH on the benzene ring of salmeterol is part of a phenol, so it is not an alcohol. 14.2 To determine whether an alcohol is 1o, 2o, or 3o, locate the C with the OH group and count the number of C’s bonded to it. A 1o alcohol has the OH group on a C bonded to one C, and so forth, as in Example 14.1. 14.3 Use the definition in Example 14.1 and Answer 14.2 to label the hydroxyl groups. 14.4 Alcohols have stronger intermolecular forces and therefore higher boiling points than hydrocarbons of comparable size and shape. Organic Compounds with O, X, or S 14–2 14.5 Hydrocarbons are insoluble in water. Low molecular weight alcohols (< 6 C’s) are water soluble, but higher molecular weight alcohols (≥ 6 C’s) are insoluble in water. 14.6 To name alcohols using the IUPAC system, follow the steps in Example 14.2: [1] Find the longest carbon chain that contains the carbon bonded to the OH group. [2] Number the carbon chain to give the OH group the lower number, and apply all other rules of nomenclature. 14.7 Work backwards to draw the structure corresponding to each name. Chapter 14–3 14.8 To draw the products of the dehydration of each alcohol, follow the steps in Example 14.3. • First find the carbon bonded to the OH group, and then identify all carbons with H’s bonded to this carbon. • Remove the elements of H and OH from two adjacent C’s, and draw a double bond between these C’s in the product. • When two different alkenes are formed, the major product has more C’s bonded to the C=C. 14.9 The Zaitsev rule states that when two different alkenes are formed, the major product has more C’s bonded to the C=C. Organic Compounds with O, X, or S 14–4 14.10 B has no H on the carbon adjacent to the carbon with the OH group, so H2O cannot be lost. 14.11 Draw the products when each alcohol is oxidized, as in Example 14.4. o • RCH2OH (1 alcohols) are oxidized to RCHO, which are then oxidized to RCOOH. o • R2CHOH (2 alcohols) are oxidized to R2CO. o • R3COH (3 alcohols) are not oxidized because they have no H atom on the C with the OH. 14.12 Ethylene glycol is oxidized to a dicarboxylic acid. 14.13 Draw the three constitutional isomers. Chapter 14–5 14.14 Look at the functional groups to determine the strength of the intermolecular forces, as in Example 14.5. The stronger the forces, the higher the boiling point. 14.15 Low molecular weight ethers are water soluble. If the ether has more than five carbons, the ether is insoluble in water. 14.16 Name each ether as in Example 14.6. 14.17 Work backwards from the IUPAC name to the structure. Organic Compounds with O, X, or S 14–6 14.18 b. Desflurane is organic, and by “like dissolves like,” organic compounds are soluble in organic solvents. 14.19 Draw the three-dimensional structure of halothane. Recall that solid lines represent bonds in the plane of the page, wedges represent bonds in front, and dashed lines represent bonds behind. 14.20 Classify each alkyl halide as 1°, 2°, or 3°. • A primary (1o) alkyl halide has a halogen on a carbon bonded to one carbon. • A secondary (2o) alkyl halide has a halogen on a carbon bonded to two carbons. • A tertiary (3o) alkyl halide has a halogen on a carbon bonded to three carbons. 14.21 Label the alkyl halide and each alcohol as 1°, 2°, or 3°. Chapter 14–7 14.22 The boiling point of alkyl halides increases with the size of the alkyl group as well as the size of the halogen. 14.23 Give the IUPAC name for each compound. Always start by finding the longest chain. 14.24 Work backwards from the name to the structure. Organic Compounds with O, X, or S 14–8 14.25 Chlorofluorocarbons (CFCs) have the general molecular structure CFxCl4 – x. Hydrochlorofluorocarbons (HCFCs) contain the elements of H, Cl, and F bonded to carbon, whereas hydrofluorocarbons (HFCs) contain the elements of H and F bonded to carbon. a. CF3Cl is a CFC. b. CHFCl2 is an HCFC. c. CH2F2 is an HFC. 14.26 Name the thiols using the steps in Example 14.7. 14.27 When thiols are oxidized, they form disulfides. Disulfides are converted back to thiols with a reducing agent. 14.28 Solutions to End-of-Chapter Problems 14.29 To determine whether an alcohol is 1o, 2o, or 3o, locate the C with the OH group and count the number of C’s bonded to it. A 1o alcohol has the OH group on a C bonded to one C, and so forth, as in Example 14.1. Chapter 14–9 14.30 To determine whether an alcohol is 1o, 2o, or 3o, locate the C with the OH group and count the number of C’s bonded to it. A 1o alcohol has the OH group on a C bonded to one other C, and so forth, as in Example 14.1. OH CH3 CH3 CH2CH2CH3 a. b. (CH3)3CCH2CH2OH c. CH3CH2CH2CHOH d. CH3CH2CH2CCH2OH CH3 C bonded to 3 C's C bonded to 1C C bonded to 2 C's C bonded to 1 C 3° alcohol 1° alcohol 2° alcohol 1° alcohol 14.31 Classify each alkyl halide as 1°, 2°, or 3°. • A primary (1o) alkyl halide has a halogen on a carbon bonded to one carbon. • A secondary (2o) alkyl halide has a halogen on a carbon bonded to two carbons. • A tertiary (3o) alkyl halide has a halogen on a carbon bonded to three carbons. 14.32 Classify each alkyl halide as 1°, 2°, or 3°. • A primary (1o) alkyl halide has a halogen on a carbon bonded to one carbon. • A secondary (2o) alkyl halide has a halogen on a carbon bonded to two carbons. • A tertiary (3o) alkyl halide has a halogen on a carbon bonded to three carbons. C bonded to 1 C 1° alkyl halide CH3 CH2Br CH3C CHCH2CH2CCH CH2 Cl C bonded to 3 C's 3° alkyl halide 14.33 Draw a structure that fits each description. 14.34 Draw a structure that fits each description. OH CH2Cl a. CH3CH2CHCH2CH CH2 b. O c. CH3CH2CH CH 2° alcohol cyclic ether 3 1° alkyl halide Organic Compounds with O, X, or S 14–10 14.35 Draw the structure of the six constitutional isomers of molecular formula C5H12O that contain an ether functional group. 14.36 Draw the structure of the four constitutional isomers of molecular formula C3H6Br2. Br Br Br CH3 C CH3 CH3 CHCH2Br CH3CH2C H BrCH2CH2CH2Br Br Br 14.37 Chapter 14–11 14.38 2 C's: ethyl group ether 5 C's: pentyl group a. CH3CH3 O CH2CH2CH2CH2CH3 ethyl pentyl ether 2 b. CH3CH2CH2CH2CHCH3 6C's: hexanethiol 2-hexanethiol SH thiol 14.39 14.40 a. b. 2° alcohol c. 3-ethylcyclohexanol 3 1 C bonded to 2 C's O H 14.41 To name alcohols using the IUPAC system, follow the steps in Example 14.2: [1] Find the longest carbon chain that contains the carbon bonded to the OH group. [2] Number the carbon chain to give the OH group the lower number, and apply all other rules of nomenclature. Organic Compounds with O, X, or S 14–12 14.42 To name alcohols using the IUPAC system, follow the steps in Example 14.2: [1] Find the longest carbon chain that contains the carbon bonded to the OH group. [2] Number the carbon chain to give the OH group the lower number, and apply all other rules of nomenclature. 3 6 a. CH3CH2CHCH2CH2CHCH3 CH3CH2CHCH2CH2CHCH3 6-methyl-3-heptanol OH CH3 OH CH3 7 C's in the longest chain OH group at C3 methyl group at C6 heptanol Chapter 14–13 OH group at C1 1 CH2OH CH2OH b. CH3CH2CH2CHCH2CH3 CH3CH2CH2CHCH2CH3 2-ethyl-1-pentanol 2 5 C's in the longest chain pentanol ethyl group at C2 methyl group at C3 3 c. CH3(CH2)3CHCH3 CH3(CH2)3CHCH3 3-methyl-1-heptanol CH2CH2OH CH2CH2OH 1 7 C's in the longest chain OH group at C1 heptanol OH OH d. HOCH2CHCH2OH HOCH2CHCH2OH 1, 2,3-propanetriol 3 C's in the longest chain propanol OH groups at C1, C2, C3 OH OH CH2CH3 CH2CH3 e. 1-ethyl-2-methylcyclopentanol OH and ethyl at C1 CH3 CH3 5 C's in the ring methyl at C2 cyclopentanol OH at C1 HO CH3 HO 1 3 CH3 f. 3,4-dimethylcyclohexanol 4 CH3 CH3 6 C's in the ring methyls at C3 and C4 cyclohexanol 14.43 Work backwards to draw the structure corresponding to each name. Organic Compounds with O, X, or S 14–14 14.44 Work backwards to draw the structure corresponding to each name. OH a. 3-methyl-3-pentanol CH3CH2CCH2CH3 5 C chain with OH at C3 CH3 and methyl at C3 3 2 4 b. 4-methyl-2-pentanol CH3CHCH2CHCH3 5 C chain with OH at C2 OH CH3 and methyl at C4 2 OH 4 c.
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