Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 6, Problem 6.48SP
A solution of pure (S)-2-iodobutane ([α]=+15.90°) in acetone is allowed to react with radioactive iodide, 131|−, until 1.0% of the iodobutane contains radioactive iodine. The specific rotation of this recovered iodobutane is found to be +15.58°.
- a. Determine the percentages of (R)- and (S)-2-iodobutane in the product mixture.
- b. What does this result suggest about the mechanism of the reaction of 2-iodobutane with iodide ion?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Useful Information:
sodium metam: Commercial grade sodium metam is 33% pure sodium metam by weight and has a density of 1.2 g/mL.
Hydrolysis of metam (Methyl isothiocynate) + H2S
Rate constants for hydrolysis for metam (base catalyzed hydrolysis is negligible)
= 300 mol -1 L. sec -1 , = 1 x 10-8 sec-1
Metam also undergoes photolysis to methyl isothiocyanate with a half-life of 1.6 hrs.
Data for Sacramento River
discharge Q = 75,000 L/min
mean depth = 0.30 m
pH = 7.8
mean width = 3.2 m
dispersion coefficient D = 1.6 x 102 m2/min
Assuming the spill acts acts as a single point source. How long does it take for the maximum contaminant concentration to get to Lake Shasta?
If Na+ acts as conservative (i.e., it is not transformed) tracer, calculate the maximum concentration (in g/L) at Lake Shasta. (Hint: remember that sodium only constitutes a…
Schlapbach and Hoffmann used a stereoelectronic effect to control the
stereochemistry of the reaction below. Draw the structure of the transition states
for competing reactions to explain the origin of stereoselectivity.
lag
X = CI, OR, N(Me)SO₂R
R H
+ Me
R
OH
Me X
Shown below is a carbocation intermediate in an electrophilic addition reaction of HCl with an alkene.
For the conformation shown, select each hydrogen whose bond to carbon is aligned for effective hyperconjugation with the vacant p orbital on the positively charged
carbon. Each adjacent carbon will have only one C-H bond so aligned.
• Gray = C; white = H; red = 0; blue = N; dark green = Cl; brown =Br; light green =F; purple = I; yellow = S; orange = P.
• Double click to select atoms.
• You can zoom in and out using the mouse scroll wheel (or pinch to zoom on touch screens).
Chapter 6 Solutions
Organic Chemistry (9th Edition)
Ch. 6.1 - Classify each compound as an alkyl halide, a vinyl...Ch. 6.2 - Give the structures of the following compounds. a....Ch. 6.2 - For each of the following compounds, A. give the...Ch. 6.3E - Prob. 6.4PCh. 6.4 - Prob. 6.5PCh. 6.5A - For each pair of compounds, predict which compound...Ch. 6.5B - Prob. 6.7PCh. 6.6B - Prob. 6.8PCh. 6.6B - The light-initiated reaction of...Ch. 6.6B - Show how free-radical halogenation might be used...
Ch. 6.7 - Prob. 6.11PCh. 6.7 - Prob. 6.12PCh. 6.8 - Prob. 6.13PCh. 6.9 - Predict the major products of the following...Ch. 6.9 - Prob. 6.15PCh. 6.10A - Prob. 6.16PCh. 6.11A - When diethyl ether (CH3CH2OCH2CH3) is treated with...Ch. 6.11B - Prob. 6.18PCh. 6.11B - For each pair of compounds, state which compound...Ch. 6.12 - Prob. 6.20PCh. 6.12 - Under appropriate conditions...Ch. 6.13 - Propose an SN1 mechanism for the solvolysis of...Ch. 6.13B - Prob. 6.23PCh. 6.13B - 3-Bromocyclohexene is a secondary halide, and...Ch. 6.15 - Prob. 6.25PCh. 6.15 - Prob. 6.26PCh. 6.16 - For each reaction, give the expected substitution...Ch. 6.16 - Prob. 6.28PCh. 6.16 - Prob. 6.29PCh. 6 - Prob. 6.30SPCh. 6 - Draw the structures of the following compounds. a....Ch. 6 - Give systematic (IUPAC) names for the following...Ch. 6 - Prob. 6.33SPCh. 6 - Predict the compound in each pair that will...Ch. 6 - Prob. 6.35SPCh. 6 - Give two syntheses for (CH3)2CHOCH2CH3, and...Ch. 6 - Prob. 6.37SPCh. 6 - Prob. 6.38SPCh. 6 - Chlorocyclohexane reacts with sodium cyanide...Ch. 6 - Give the substitution products expected from...Ch. 6 - Prob. 6.41SPCh. 6 - Prob. 6.42SPCh. 6 - Two of the carbocations in Problem6-42 are prone...Ch. 6 - Prob. 6.44SPCh. 6 - Predict the products of the following SN2...Ch. 6 - Prob. 6.46SPCh. 6 - Strawberry growers have used large quantities of...Ch. 6 - A solution of pure (S)-2-iodobutane ([]=+15.90) in...Ch. 6 - Prob. 6.49SPCh. 6 - Give a mechanism to explain the two products...Ch. 6 - Prob. 6.51SPCh. 6 - Because the SN1 reaction goes through a flat...Ch. 6 - Prob. 6.53SPCh. 6 - Furfuryl chloride can undergo substitution by both...Ch. 6 - Prob. 6.55SPCh. 6 - The following reaction takes place under...Ch. 6 - Propose mechanisms to account for the observed...Ch. 6 - Prob. 6.58SPCh. 6 - Prob. 6.59SP
Additional Science Textbook Solutions
Find more solutions based on key concepts
Practice Exercise 1
Which of the following factors determines the size of an atom? a. the volume of the nucleus...
Chemistry: The Central Science (13th Edition)
Practice Problem ATTEMPT
Write the rate expressions for each of the following reactions:
(a)
(b)
(c)
Chemistry
The chapter sections to review are shown in parentheses at the end of each problem. A "chemical-free” shampoo i...
Basic Chemistry
Q1. What is the empirical formula of a compound with the molecular formula
Chemistry: A Molecular Approach
Fully developed conditions are known to exist for water flowing through a 25-nim-diameer tube at 0.01 kg/s and ...
Fundamentals of Heat and Mass Transfer
Consider a sample of ideal gas initially in a volume V at temperature T and pressure P. Does the entropy of thi...
General Chemistry: Principles and Modern Applications (11th Edition)
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
- 8. Write the product of the reaction in three dimensions and indicate if the methyl groups in the product are cis or trans. + H,0,Cl, H,C CH, 9. Write the product of the reaction in three dimensions and indicate if the resulting product is meso or formed as a racemic mixture. CH3 Cl. CCI, solvent H3C 10. Write the mechanism of the following reaction. Use curved arrows to show the movement of electrons in each step. Draw the bromonium ion intermediate emphasizing the position of positive charge. Draw and write "cis" or "trans" of the high priority groups in the product for full credit. + Br-OH, water, CHarrow_forward12.Use of KMnO, to effect oxidative cleave of the alkene J, C3H16, yields two fragments, one of which is butanoic acid and the other a ketone, Q. When J reacts with one molar equivalent of H-Cl, the alkyl halide K, C3H17CI, is formed. What are the structures of J, J, and Q? Write all the reactions, and show your reasoning.arrow_forwardCH3 || CH3 H₂O H2SO4 CH3CHCH2CH2C—ОCH₂CH₂CHCH3 a. Draw the structure of the tetrahedral intermediate INITIALLY-FORMED in the reaction shown. • • • You do not have to consider stereochemistry. Do not include counter-ions, e.g., Na+, I, in your answer. In cases where there is more than one answer, just draw one. √n [ ChemDoodle Ⓡ b. Draw the structures of the organic products of the acyl transfer reaction. • You do not have to consider stereochemistry. Draw the neutral form of the products; no charges. Draw one structure per sketcher. Add additionalarrow_forward
- Draw a structural formula for the substitution product of the reaction shown below. H/ ● (CH3)3C |YY Br ΔΟ H Na • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If more than one stereoisomer of product is formed, draw both. Separate multiple products using the + sign from the drop-down menu. • Products that are initially formed as ions should be drawn in their neutral forms. SH acetone [Farrow_forward5-The hydrolysis of a series of ethyl benzoates by hydroxide ion in 85% aqueous ethanol has been investigated. A Hammett plot of the second order rate constants (K) gave a reaction constant p = 2.56. Calculate how much faster ethyl 4- nitrobenzoate will undergo base catalyzed hydrolysis compared to ethyl benzoate under similar conditions. O,Narrow_forwardChemistry Part 5 out of 6 Choose the most appropriate reagent(s) for the conversion of 1-phenylethyl bromide to methyl 1-phenylethyl sulfide. A H₂S C CH₂SH NBS, ROOR CCI4 heat E CH₂SO₂H Br BSg, NaOH reagent(s) DNaSCH3, DMF SCH3arrow_forward
- 6. Frequently, the term "free rotation" is used to describe rotation about C-C single bonds. The barrier for rotation about the C-C bond of ethane is 3 kcal/mol. What is the rate constant, k [in units of rotations per second], for this process assuming that the Arrhenius pre-exponential factor, A, is 105, and T = 298 K? Show your work. 13arrow_forwardIn the Directive Effects in the Bromination of Vanillin, the following reaction was performed: сно сно Br2 CH,CH,CO,H Br OMe OMe OH OH vanillin 5-bromovanillin Which of the following are correct resonance structures of the intermediate cation in this reaction? Mark all that are correct. CHO сно CHO H. H. Н. Br OMe Br OMe Br OMe ÖH OH OH B CHO CHO Br H- CHO H. Br OMe Br OMe OMe OH OH OH D Earrow_forwardThe following is a nucleophilic substitution reaction of R-3-chloro-2-methylhexane with "OCH3. The optical rotation of the solution after the reaction was complete was +11.4° CH3 Н. H3C. CH3 "OCH, H2 H. The mechanism for this reaction is SN2 Draw the organic molecule(s) which is(are) formed in this reaction. Do not include molecules like H,O or HCl. Draw the specific configuration (R or S) at any chiral carbons within your product(s). If both configurations are formed in the product(s), draw both as separate molecules/products.arrow_forward
- Consider the following reaction. O + 0 CHBr3 Draw the major organic product formed in this reaction. 81 + [**** (CH3)3CO¹K+ • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Include H atoms at chiral centers only. • Show stereochemistry in a meso compound. If the reaction produces a racemic mixture, just draw one stereoisomer. - √n [F] ?arrow_forward3) The Suzuki-Miyaura reaction is an effective method for generating a C-C bond between two sp2- hybridized C-atoms. Answer the following questions about the coupling of 3-furanylboronic acid and 1-bromo-4-nitrobenzene to form 3-(4'-nitrophenyl)furan. он -B OH NO2 Pd. cat Br NO2 KOH/solvent a) Furan and its derivatives are heteroaromatic compounds that follow Hückel's rule for aromatic n systems. Identify the approximate hybridization of each O-atom lone pair and the O-atom in furan. Approximate O-atom lone pair hybridization = Approximate O-atom lone pair hybridization = Approximate O-atom hybridization =arrow_forwardThe following Diels-Alder cycloaddition was recently performed by Mukherjee et al. CH2CI2 -CO,Et + ACN ACO,E NC -78°C, 8h CO,Et 1 ČN 25% 75% When cyclopentadiene is added in excess, the reaction is pseudo-1st order with respect to the fumaric nitrile ester. If 4 hours represents the time for half of the original amount of ester to be consumed, then calculate the amount of 1 and 2 diastereoisomers that are formed after 90 min if performed with 75.0 mmol of ester.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License