EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 6.5, Problem 9P
The pKa of a protonated alcohol is about –2.5, and the pKa of an alcohol is about 15. Therefore, as long as the pH of the solution is greater than ___ and less than ________, more than 50% of 2-propanol (the product of the reaction on p. 244) will be in its neutral. nonprotonated form.
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1. Consider the solubility and boiling point of the following pair of compounds: n-butyl alcohol and diethyl ether. The boiling points for the compounds are 118 °C and 35 °C respectively. The solubility for both compounds is the same (8g/100g water). Explain this observation for (i) boiling point disparity; (ii) solubility similarity
a. H-bonds form in diethyl ether; n-butyl alcohol forms H-bonds in water
b. H-bonds form in n-butyl alcohol; diethyl ether forms H-bonds in water
c. H-bonds in n-butyl alcohol; Both compounds form H-bonds in water
d. Both compounds form H-bonds; Both compounds form H-bonds in water
2. Account for the bond angle differences between (i) H-C-H (109.5°) in methane and H-S-H (90°); H-C-H (109.5°) and H-O-H (107.5°) in water.
a. The H-S-H has two lone pairs; The H-O-H has two lone pairs
b. The H-S-H has no hybridization at p-orbitals; The H-O-H has two lone pairs
c. The H-S-H has two lone pairs; The H-O-H has no hybridization…
Consider propanoic acid and pentanoic acid and the corresponding alcohols with the same number of carbons, propanol and pentanol. Which is more soluble in water, the alcohol or the carboxylic acid? Why? [you should have two selections.]
a. Propanoic acid and pentanoic acid are more soluble in water than the corresponding alcohol
b. The solubility of carboxylic acids in water decreases with increasing chain length.
c. Propanol and pentanol are more soluble in water than the corresponding carboxylic acid
d. The solubility of alcohols in water decreases with increasing chain length.
Alcohols are generally more soluble in water than carboxylic acids of the same chain length because of increased hydrogen bonding with the -COH functional group.
e. Carboxylic acids are generally more soluble in water than alcohols of the same chain length because of increased hydrogen bonding with the -COOH functional group.
Write the chemical equation for a pentanoate ion acting as base when it reacts with hydrochloric acid (HCI).
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Chapter 6 Solutions
EBK ORGANIC CHEMISTRY
Ch. 6.1 - Draw the mechanism for the reaction of cyclohexene...Ch. 6.2 - a. How many bond orbitals are avilable for...Ch. 6.2 - Prob. 3PCh. 6.2 - Prob. 4PCh. 6.3 - Prob. 5PCh. 6.4 - Prob. 6PCh. 6.4 - Prob. 7PCh. 6.4 - What alkene should be used to synthesize each of...Ch. 6.5 - The pKa of a protonated alcohol is about 2.5, and...Ch. 6.5 - Prob. 10P
Ch. 6.5 - Prob. 11PCh. 6.6 - a. What is the major product or each or the...Ch. 6.6 - Prob. 14PCh. 6.6 - Prob. 15PCh. 6.7 - What is the major product obtained from the...Ch. 6.8 - Which is more highly regionselective: reaction of...Ch. 6.8 - Prob. 19PCh. 6.9 - What will be the product of the preceding reaction...Ch. 6.9 - Prob. 21PCh. 6.9 - Prob. 22PCh. 6.9 - Prob. 23PCh. 6.9 - What is the product of the addition of 1Cl to...Ch. 6.9 - What will be the major product obtained from the...Ch. 6.9 - Propose a mechanism for the following reaction:Ch. 6.10 - Draw structures for the following: a. 24...Ch. 6.10 - What alkene would you treat with a peroxyacid in...Ch. 6.11 - What products are formed when the following...Ch. 6.11 - Prob. 31PCh. 6.11 - Prob. 32PCh. 6.11 - The following product was obtained from the...Ch. 6.12 - What characteristics must the reactant of a...Ch. 6.13 - Prob. 36PCh. 6.13 - What stereoisomers are obtained from each of the...Ch. 6.13 - Prob. 41PCh. 6.13 - Prob. 42PCh. 6.13 - Prob. 43PCh. 6.13 - Prob. 45PCh. 6.13 - Prob. 46PCh. 6.13 - Prob. 47PCh. 6.13 - Prob. 48PCh. 6.13 - Prob. 49PCh. 6.13 - Prob. 50PCh. 6.14 - Prob. 51PCh. 6.16 - Prob. 53PCh. 6.16 - Explain why 3-methykyclohexene should not be used...Ch. 6 - Prob. 55PCh. 6 - Prob. 56PCh. 6 - Prob. 57PCh. 6 - What is the major product of the reaction of...Ch. 6 - Give two names for each of the following:Ch. 6 - Prob. 60PCh. 6 - What are the products of the following reactions?...Ch. 6 - When 3-methyl-1-butene reacts with HBr, two alkyl...Ch. 6 - Draw curved arrows to show the flow of electrons...Ch. 6 - What reagents are needed to carry out the...Ch. 6 - Prob. 65PCh. 6 - Prob. 66PCh. 6 - Prob. 67PCh. 6 - What is more stable? a. CH3C+HCH3orCH3C+HCH2ClCh. 6 - Prob. 69PCh. 6 - a. Draw the product or products that will be...Ch. 6 - Prob. 71PCh. 6 - The second-order rate constant (in units of M1s1)...Ch. 6 - Which compound has the greater dipole moment?Ch. 6 - Prob. 74PCh. 6 - Prob. 75PCh. 6 - Prob. 76PCh. 6 - Prob. 77PCh. 6 - Prob. 78PCh. 6 - Prob. 79PCh. 6 - Prob. 80PCh. 6 - Prob. 81PCh. 6 - Prob. 82PCh. 6 - Prob. 83PCh. 6 - Prob. 84PCh. 6 - Prob. 85PCh. 6 - Prob. 86PCh. 6 - Draw the products of the following reactions. If...Ch. 6 - Prob. 88PCh. 6 - Prob. 89PCh. 6 - Prob. 90PCh. 6 - Two chemists at Dupont found that lCH2Znl is...Ch. 6 - Prob. 92PCh. 6 - Prob. 93PCh. 6 - What alkene gives the product shown after...Ch. 6 - Prob. 95PCh. 6 - Prob. 96PCh. 6 - Prob. 97PCh. 6 - Prob. 98PCh. 6 - Prob. 99PCh. 6 - Prob. 100PCh. 6 - Propose a mechanism for the following reaction:Ch. 6 - Prob. 102PCh. 6 - Prob. 103P
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