Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
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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True or False: Write True if the statement is correct and False if otherwise.i. Esters are formed by the reaction of a salt with an acid.ii. In such reactions, the —OR group from the alcohol replaces the —OH group in the carboxylic acid.iii. Esters are polar compounds, but they cannot form hydrogen bonds to each other.iv. Their boiling points are lower than those of alcohols and acids of similar molecular massv. Esters cannot be converted back to carboxylic acids and alcohols under either acidic or basicconditions.vi. Thioesters are sulfur-containing analogs of esters in which a —SR group has replaced the —COOHgroup.vii. Polyesters are polymers in which the monomers (diacids and dialcohols) are joined through esterlinkages.viii. An ester is named as an alkyl carboxylate.
1. Draw the carboxylic acids formed by the oxidation of each of the following molecules.
HOH₂C
H2
CH3
H3CH2C
H
+
2. Draw the esters formed by the following reactions.
a.
H3C
H3C-C-C
H₂
H3C.
OH
H3C
OH
b.
H3C
H3CHCH2CH2C-
རི
OH
+ H3C.
`CH2CH3
OH
H₂
3. Indicate the products of the following reaction:
LCH
CH3 + H₂O
H3CH2CH2C
CH₂OH
in one another (like dissolves like)
OH makes them polar and since water is also polar, they ar
Alcohols are soluble in water. They are soluble in water
19. Are alcohols soluble or insoluble in water?
Carboxylic acids
*both at could furthe
a.
b.
H₂SO4,
180°C
H
H
b. 2 ketone
alder
OH
4. Based on Zaitsev's rule, write the major/minor products, as well as the side product, for
the following dehydration reaction of alcohols and label the major product.
5. First indicate the classification of alcohol (primary, secondary or tertiary), then using the
classification, draw the aldehyde, ketone, carboxylic acid or no product formed when
most oxidation reactions
the following alcohols are mildly oxidized. *keep in mind there is a byproduct of water in
HO
H-C-C-C-H
H H H
OH
Classify the alcohol: 1°, 2° or 3⁰
-
90
Classify the alcohol: 1°, 2° or 3⁰
a.
RES
[0]
IDT
[o]
OXA
6. In the following structure list all 7 of the functional groups present.
Chapter 6 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
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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