EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 9780100591318
Author: McMurry
Publisher: YUZU
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 11.SE, Problem 34MP
Reaction of iodoethane with CN- yields a small amount of isonitrile, CH3CH2N≡C, along with the nitrile CH3CH2N≡N, as the major product. Write electron-dot structures for both products, assign formal charges as necessary, and propose mechanisms to account for their formation.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
The data for the potential difference of a battery and its temperature are given in the table. Calculate the entropy change in J mol-1 K-1 (indicate the formulas used).Data: F = 96485 C mol-1
In a cell, the change in entropy (AS) can be calculated from the slope of the E° vs
1/T graph. The slope is equal to -AS/R, where R is the gas constant. Is this correct?
Using the Arrhenius equation, it is possible to establish the relationship between the rate constant (k) of a chemical reaction and the temperature (T), in Kelvin (K), the universal gas constant (R), the pre-exponential factor (A) and the activation energy (Ea). This equation is widely applied in studies of chemical kinetics, and is also widely used to determine the activation energy of reactions. In this context, the following graph shows the variation of the rate constant with the inverse of the absolute temperature, for a given chemical reaction that obeys the Arrhenius equation. Based on the analysis of this graph and the concepts acquired about the kinetics of chemical reactions, analyze the following statements:
I. The activation energy (Ea) varies with the temperature of the system.
II. The activation energy (Ea) varies with the concentration of the reactants.
III. The rate constant (K) varies proportionally with temperature.
IV. The value of the…
Chapter 11 Solutions
EBK ORGANIC CHEMISTRY
Ch. 11.1 - Prob. 1PCh. 11.2 - Prob. 2PCh. 11.2 - Prob. 3PCh. 11.3 - Prob. 4PCh. 11.3 - Prob. 5PCh. 11.3 - Rank the following compounds in order of their...Ch. 11.3 - Organic solvents like benzene, ether, and...Ch. 11.4 - Prob. 8PCh. 11.4 - Prob. 9PCh. 11.4 - Prob. 10P
Ch. 11.5 - Rank the following substances in order of their...Ch. 11.5 - 3-Bromo-1-butene and 1-bromo-2-butene undergo SN1...Ch. 11.5 - Prob. 13PCh. 11.6 - Review the mechanism of geraniol biosynthesis...Ch. 11.7 - Prob. 15PCh. 11.7 - What alkyl halides might the following alkenes...Ch. 11.8 - Prob. 17PCh. 11.8 - Prob. 18PCh. 11.9 - Prob. 19PCh. 11.12 - Prob. 20PCh. 11.SE - Prob. 21VCCh. 11.SE - From what alkyl bromide was the following alkyl...Ch. 11.SE - Prob. 23VCCh. 11.SE - Prob. 24VCCh. 11.SE - Prob. 25MPCh. 11.SE - Prob. 26MPCh. 11.SE - Prob. 27MPCh. 11.SE - Prob. 28MPCh. 11.SE - Prob. 29MPCh. 11.SE - Prob. 30MPCh. 11.SE - Prob. 31MPCh. 11.SE - Prob. 32MPCh. 11.SE - Metabolism of S-adenosylhomocysteine (Section...Ch. 11.SE - Reaction of iodoethane with CN- yields a small...Ch. 11.SE - One step in the urea cycle for ridding the body of...Ch. 11.SE - Prob. 36MPCh. 11.SE - Prob. 37MPCh. 11.SE - Propose a mechanism for the following reaction, an...Ch. 11.SE - Prob. 39APCh. 11.SE - The following Walden cycle has been carried out....Ch. 11.SE - Prob. 41APCh. 11.SE - Which reactant in each of the following pairs is...Ch. 11.SE - Prob. 43APCh. 11.SE - Prob. 44APCh. 11.SE - Prob. 45APCh. 11.SE - Prob. 46APCh. 11.SE - Prob. 47APCh. 11.SE - Prob. 48APCh. 11.SE - Propose structures for compounds that fit the...Ch. 11.SE - What products would you expect from the reaction...Ch. 11.SE - Prob. 51APCh. 11.SE - Prob. 52APCh. 11.SE - Prob. 53APCh. 11.SE - Prob. 54APCh. 11.SE - Prob. 55APCh. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Prob. 58APCh. 11.SE - Prob. 59APCh. 11.SE - Ethers can often be prepared by SN2 reaction of...Ch. 11.SE - Show the stereochemistry of the epoxide (see...Ch. 11.SE - Prob. 62APCh. 11.SE - In addition to not undergoing substitution...Ch. 11.SE - The tosylate of (2R, 3S)-3-phenyl-2-butanol...Ch. 11.SE - Prob. 65APCh. 11.SE - Prob. 66APCh. 11.SE - Prob. 67APCh. 11.SE - Prob. 68APCh. 11.SE - Prob. 69APCh. 11.SE - (S)-2-Butanol slowly racemizes on standing in...Ch. 11.SE - Reaction of HBr with (R)-3-methyl-3-hexanol leads...Ch. 11.SE - Treatment of 1-bromo-2-deuterio-2-phenylethane...Ch. 11.SE - Prob. 73APCh. 11.SE - Prob. 74APCh. 11.SE - In light of your answer to Problem 11-74, explain...Ch. 11.SE - Prob. 76APCh. 11.SE - Compound X is optically inactive and has the...Ch. 11.SE - When a primary alcohol is treated with...Ch. 11.SE - Prob. 79APCh. 11.SE - Amines are converted into alkenes by a two-step...Ch. 11.SE - The antipsychotic drug flupentixol is prepared by...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- In an electrolytic cell, indicate the formula that relates E0 to the temperature T.arrow_forward-- 14:33 A Candidate Identification docs.google.com 11. Compound A can transform into compound B through an organic reaction. From the structures below, mark the correct one: HO A تھے۔ די HO B ○ A) Compounds A and B are isomers. B) Both have the same number of chiral carbons. C) Compound A underwent an addition reaction of Cl2 and H2O to form compound B. D) Compound A underwent a substitution reaction forming the intermediate chlorohydrin to obtain compound B. E) Compound A underwent an addition reaction of Cl2 forming the chloronium ion and then added methanol to obtain compound B. 60arrow_forward-- 14:40 A Candidate Identification docs.google.com 13. The compound 1-bromo-hex-2-ene reacts with methanol to form two products. About this reaction, mark the correct statement: OCH3 CH3OH Br OCH3 + + HBr A B A) The two products formed will have the same percentage of formation. B) Product B will be formed by SN1 substitution reaction with the formation of an allylic carbocation. C) Product A will be formed by SN1 substitution reaction with the formation of a more stable carbocation than product B. D) Product A will be formed by an SN2 substitution reaction occurring in two stages, the first with slow kinetics and the second with fast kinetics. E) The two compounds were obtained by addition reaction, with compound B having the highest percentage of formation. 57arrow_forward
- -- ☑ 14:30 A Candidate Identification docs.google.com 10. Amoxicillin (figure X) is one of the most widely used antibiotics in the penicillin family. The discovery and synthesis of these antibiotics in the 20th century made the treatment of infections that were previously fatal routine. About amoxicillin, mark the correct one: HO NH2 H S -N. HO Figura X. Amoxicilina A) It has the organic functions amide, ester, phenol and amine. B) It has four chiral carbons and 8 stereoisomers. C) The substitution of the aromatic ring is of the ortho-meta type. D) If amoxicillin reacts with an alcohol it can form an ester. E) The structure has two tertiary amides. 62arrow_forwardThe environmental police of a Brazilian state received a report of contamination of a river by inorganic arsenic, due to the excessive use of pesticides on a plantation on the riverbanks. Arsenic (As) is extremely toxic in its many forms and oxidation states. In nature, especially in groundwater, it is found in the form of arsenate (AsO ₄ ³ ⁻ ), which can be electrochemically reduced to As ⁰ and collected at the cathode of a coulometric cell. In this case, Potentiostatic Coulometry (at 25°C) was performed in an alkaline medium (pH = 7.5 throughout the analysis) to quantify the species. What potential (E) should have been selected/applied to perform the analysis, considering that this is an exhaustive electrolysis technique (until 99.99% of all AsO ₄ ³ ⁻ has been reduced to As ⁰ at the electrode, or n( final) = 0.01% n( initial )) and that the concentration of AsO ₄ ³ ⁻ found in the initial sample was 0.15 mmol/L ? Data: AsO ₄ 3 ⁻ (aq) + 2 H ₂ O ( l ) + 2 e ⁻ → A s O ₂ ⁻ ( a…arrow_forward-- 14:17 15. Water-soluble proteins are denatured when there is a change in the pH of the environment in which they are found. This occurs due to the protonation and deprotonation of functional groups present in their structure. Choose the option that indicates the chemical bonds modified by pH in the protein represented in the following figure. E CH2 C-OH CH2 H₂C H₁C CH CH3 CH3 CH CH₂-S-S-CH₂- 910 H B -CH2-CH2-CH2-CH₂-NH3* −0—C—CH₂- ○ A) A, C e D. • В) Вес ○ C) DeE ○ D) B, De E ○ E) A, B e C 68arrow_forward
- Suppose sodium sulfate has been gradually added to 100 mL of a solution containing calcium ions and strontium ions, both at 0.15 mol/L. Indicate the alternative that presents the percentage of strontium ions that will have precipitated when the calcium sulfate begins to precipitate. Data: Kps of calcium sulfate: 2.4x10 ⁻ ⁵; Kps of strontium sulfate: 3.2x10 ⁻ ⁷ A) 20,2 % B) 36,6 % C) 62,9 % D) 87,5 % E) 98.7%arrow_forward14:43 A Candidate Identification docs.google.com 14. The following diagrams represent hypothetical membrane structures with their components numbered from 1 to 6. Based on the figures and your knowledge of biological membranes, select the correct alternative. | 3 5 || 人 2 500000 6 A) Structures 1, 3, 5, 2 and 4 are present in a constantly fluid arrangement that allows the selectivity of the movement ○ of molecules. Structure 4, present integrally or peripherally, is responsible for this selection, while the quantity of 6 regulates the fluidity. B) The membranes isolate the cell from the environment, but allow the passage of water-soluble molecules thanks to the presence of 2 and 3. The membrane in scheme is more fluid than that in 55arrow_forward12. Mark the correct statement about reactions a and b : a. Br + -OH Br b. + Br H₂O + Br -OH + H₂O A) The reactions are elimination reactions, with reaction "a" being of type E2 and reaction "b" being of type E1. B) Reaction "a" is an E2 type elimination occurring in one step and reaction "b" is an SN1 type substitution. C) Both reactions can result in the formation of carbocation, but in reaction "b" the most stable carbocation will be formed. D) Both reactions occur at the same rate ○ and have the same number of reaction steps. E) Reaction "b" is an E2 type elimination occurring in two steps and reaction "a" is an SN2 type substitution.arrow_forward
- Chloroform, long used as an anesthetic and now considered carcinogenic, has a heat of vaporization of 31.4 kJ/mol. During vaporization, its entropy increases by 94.2 J/mol.K. Therefore, select the alternative that indicates the temperature, in degrees Celsius, at which chloroform begins to boil under a pressure of 1 atm. A) 28 B) 40 C) 52 D) 60 E) 72arrow_forwardIf we assume a system with an anodic overpotential, the variation of n as a function of current density: 1. at low fields is linear 2. at higher fields, it follows Tafel's law Obtain the range of current densities for which the overpotential has the same value when calculated for 1 and 2 cases (maximum relative difference of 5% compared to the behavior for higher fields). To which overpotential range does this correspond? Data: i = 1.5 mA cm², T = 300°C, B = 0.64, R = 8.314 J K1 mol-1 and F = 96485 C mol-1.arrow_forwardAnswer by equation pleasearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
General Chemistry | Acids & Bases; Author: Ninja Nerd;https://www.youtube.com/watch?v=AOr_5tbgfQ0;License: Standard YouTube License, CC-BY