Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
expand_more
expand_more
format_list_bulleted
Question
Chapter 9, Problem 9.69AP
Interpretation Introduction
Interpretation:
An explanation to why Grignard reagent can be dissolved in hydrocarbon solvents if a tertiary
Concept introduction:
Solubility of the compounds into each other depends upon the kind of interaction both compounds contains. If the both the interaction are similar then dissolution process takes place. Polar compounds likes to dissolve in polar solvents and non-polar compounds like to dissolve in non-polar solvents.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
The analgesic acetaminophen is synthesized by treating 4-aminophenol with one equivalent of acetic anhydride. Draw a structural formula for acetaminophen.
In an attempt to synthesize compound C through a two-step process, a chemist discovered after
completing the first step that they had inadvertently produced two distinct compounds, A and B.
Upon examining the infrared spectroscopy (IR) results, it was observed that both A and B exhibited
peaks indicative of a ketone and an ester group. Please provide the molecular structures of A and B.
OEt
NaOEt
ΕΙΟ
A
B
In a chemical experiment, they noticed that both components, A and B, from a combined
sample turned into a new compound, C, during the following stage. The task is to
determine what compound C looks like and explain how compound A or B changes into
compound C through a reaction. Compound C should be the primary molecule
containing carbon created in this process, not just a by-product.
A
B
H3O+, H₂O, A
Mechanism =
с
Ketones and aldehydes react with sodium acetylide (the sodium salt of acetylene) to give alcohols, as shown in the following example:
R1
ОН
1. НС—с: Na*
R2
R1
R2
2. Нзо"
HC
Draw the structure of the major reaction product when the following compound reacts with sodium acetylide, assuming that the reaction takes
preferentially from the Si face of the carbonyl group.
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• You do not have to explicitly draw H atoms.
• If a group is achiral, do not use wedged or hashed bonds on it.
CH3
CH
Chapter 9 Solutions
Organic Chemistry
Ch. 9 - Prob. 9.1PCh. 9 - Prob. 9.2PCh. 9 - Prob. 9.3PCh. 9 - Prob. 9.4PCh. 9 - Prob. 9.5PCh. 9 - Prob. 9.6PCh. 9 - Prob. 9.7PCh. 9 - Prob. 9.8PCh. 9 - Prob. 9.9PCh. 9 - Prob. 9.10P
Ch. 9 - Prob. 9.11PCh. 9 - Prob. 9.12PCh. 9 - Prob. 9.13PCh. 9 - Prob. 9.14PCh. 9 - Prob. 9.15PCh. 9 - Prob. 9.16PCh. 9 - Prob. 9.17PCh. 9 - Prob. 9.18PCh. 9 - Prob. 9.19PCh. 9 - Prob. 9.20PCh. 9 - Prob. 9.21PCh. 9 - Prob. 9.22PCh. 9 - Prob. 9.23PCh. 9 - Prob. 9.24PCh. 9 - Prob. 9.25PCh. 9 - Prob. 9.26PCh. 9 - Prob. 9.27PCh. 9 - Prob. 9.28PCh. 9 - Prob. 9.29PCh. 9 - Prob. 9.30PCh. 9 - Prob. 9.31PCh. 9 - Prob. 9.32PCh. 9 - Prob. 9.33PCh. 9 - Prob. 9.34PCh. 9 - Prob. 9.35PCh. 9 - Prob. 9.36PCh. 9 - Prob. 9.37PCh. 9 - Prob. 9.38PCh. 9 - Prob. 9.39PCh. 9 - Prob. 9.40PCh. 9 - Prob. 9.41PCh. 9 - Prob. 9.42PCh. 9 - Prob. 9.43PCh. 9 - Prob. 9.44APCh. 9 - Prob. 9.45APCh. 9 - Prob. 9.46APCh. 9 - Prob. 9.47APCh. 9 - Prob. 9.48APCh. 9 - Prob. 9.49APCh. 9 - Prob. 9.50APCh. 9 - Prob. 9.51APCh. 9 - Prob. 9.52APCh. 9 - Prob. 9.53APCh. 9 - Prob. 9.54APCh. 9 - Prob. 9.55APCh. 9 - Prob. 9.56APCh. 9 - Prob. 9.57APCh. 9 - Prob. 9.58APCh. 9 - Prob. 9.59APCh. 9 - Prob. 9.60APCh. 9 - Prob. 9.61APCh. 9 - Prob. 9.62APCh. 9 - Prob. 9.63APCh. 9 - Prob. 9.64APCh. 9 - Prob. 9.65APCh. 9 - Prob. 9.66APCh. 9 - Prob. 9.67APCh. 9 - Prob. 9.68APCh. 9 - Prob. 9.69APCh. 9 - Prob. 9.70APCh. 9 - Prob. 9.71APCh. 9 - Prob. 9.72APCh. 9 - Prob. 9.73APCh. 9 - Prob. 9.74APCh. 9 - Prob. 9.75APCh. 9 - Prob. 9.76APCh. 9 - Prob. 9.77APCh. 9 - Prob. 9.78APCh. 9 - Prob. 9.79APCh. 9 - Prob. 9.80APCh. 9 - Prob. 9.81APCh. 9 - Prob. 9.82APCh. 9 - Prob. 9.83APCh. 9 - Prob. 9.84APCh. 9 - Prob. 9.85APCh. 9 - Prob. 9.86APCh. 9 - Prob. 9.87AP
Knowledge Booster
Similar questions
- 17-34 Explain why liquid aldehydes are often stored under an atmosphere of nitrogen rather than in air.arrow_forwardH NH₂ ཡིནྣཾ ༥ ཨ ཨནྡྷ༥ ༠ ཨི་ཝཱ, ཙ ཨ་ར༩ H NH3+ the acidity of the amine ion drives the reaction to shift toward the conjugate base of the carboxylic acid product. the resulting carboxylic acid ion is a weaker base than an acetate ion. O aldehydes are more reactive toward nucleophiles than ketones. Onucleophilic attack occurs preferentially at the less hindered carbon of the formyl group.arrow_forwardEarly organic chemists used the Hofmann elimination reaction as the last step of a process known as a Hofmann degradation—a method used to identify amines. In a Hofmann degradation, an amine is methylated with excess methyl iodide in a basic solution, treated with silver oxide to convert the quaternary ammonium iodide to a quaternary ammonium hydroxide, and then heated to allow it to undergo a Hofmann elimination. Once the alkene product is identified, working backward gives the structure of the amine. Identify the amine in each of the following cases: a. 4-Methyl-2-pentene is obtained from the Hofmann degradation of a primary amine. b. 3-Methyl-1-butene is obtained from the Hofmann degradation of a primary amine. c. 2-Methyl-1-3-butadiene is obtained from two successive Hofmann degradations of a secondary amine.arrow_forward
- Ethyl butyrate, CH3CH2CH2CO2CH2CH3CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring. It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l)CH3CH2CH2CO2H(l)+CH2CH3OH(l)⟶H+CH3CH2CH2CO2CH2CH3(l)+H2O(l) A chemist ran the reaction and obtained 5.40 g of ethyl butyrate. What was the percent yield, The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 7.45g of butanoic acid and excess ethanol?arrow_forwardEthyl butyrate, CH3CH2CH2CO2CH2CH3CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring. It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) Given 8.45 gg of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100%% yield? Express your answer in grams to three significant figures. A chemist ran the reaction and obtained 5.50 gg of ethyl butyrate. What was the percent yield? Express your answer as a percent to three significant figures. The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0%% yield. How many grams would be produced from 8.45 gg of butanoic acid and excess…arrow_forwardEthyl butyrate, CH3CH2CH2CO2CH2CH3CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring. It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) Part A Given 7.30 gg of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100%% yield? Express your answer in grams to three significant figures. Part B A chemist ran the reaction and obtained 5.95 gg of ethyl butyrate. What was the percent yield? Express your answer as a percent to three significant figures. Part C The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0%% yield. How many grams would be produced from 7.30 gg of…arrow_forward
- In the mid-1930s a substance was isolated from a fungus that is a parasite of ryes and other grasses. This alkaloid, lysergic acid, has been of great interest to chemists because of its strange, dramatic action on the human mind. Many derivatives of lysergic acid are known, some with medicinal applications. Perhaps the best known derivative of lysergic acid is the potent hallucinogen lysergic acid diethylamide (LSD): మగవా జి N-H LSD (CH25N;O) Like other alkaloids, LSD is a weak base, with Kp = 7.6 × 107. What is the pH of a 0.94 M solution of LSD? pH =arrow_forwardProvide the reagents for the reactions.arrow_forwardMethyl benzoate was exposed to a nitration test, although it was difficult to see the formation of a fragrant yellow solution. What produced this consequence?arrow_forward
- The ketone 2-heptanone has been identified as contributing to the odor of a number of dairy products, including condensed milk and cheddar cheese. Describe the synthesis of 2-heptanone from acetylene and any necessary organic and inorganic reagents.arrow_forwardBisphenol A is widely used as a building block in polymer synthesis and is found in the polycarbonate hard plastics of reusable drink containers, DVDs, cell phones, and other consumer goods. Bisphenol A is reported to have estrogenic activity, and its widespread occurrence in our environment is a potential concern. Describe one or two biochemical experiments that could be done to compare the activity of bisphenol A with that of its estradiol, its structural relative.arrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning