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 4.14, Problem 4.23P
- a. Compute the heats of reaction for abstraction of a primary hydrogen and a secondary hydrogen from propane by a fluorine radical.
CH3—CH2—CH3 + F· → CH3—CH2—CH2 + HF
CH3 — CH2 — CH3+F· → CH3—CH—CH3 + HF
- b. How selective do you expect free-radical fluorination to be?
- c. What product distribution would you expect to obtain from the free-radical fluorination of propane?
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
40. Deuterium oxide, D20, is water that contains the stable hydrogen isotope 2H,
usually shown as D. When dissolved in deuterium oxide, ethanol undergoes the
following reaction: *
CH3CH2OH + D½0 →
CH;CH2OD + HOD
What is the best way of showing that this reaction has occurred?
A. By testing the product with phosphorus pentachloride and not getting steamy fumes.
B. By determining the mass spectrum of the mixture and showing peaks at m/z values of 20
and 46.
C. By fractionally distilling the mixture and determining the amount of CH3CH2OD using a
Geiger counter.
D. By determining the mass spectrum of the mixture and showing peaks at m/z values by 19
and 47.
A
В
O D
7) You want to synthesize 3-methyl-2-pentene from 2-chloro-3-methylpentane. Which reagent
would you use?
a. HCI, heat
b. NH:(aq), 25°C
c. CH:CO2NA, CH:CO2H, heat
d. CH3CH2ONA, CH3CH2OH, heat
e. CН:CH2ОН, heat
Draw structural formulas for all alkenes that could be used to prepare the alcohol shown below by
oxymercuration.
OH
?
1. Hg(OAc)2, H₂O
(CH3)2CHCCH(CH3)2
2. NaBH4
CH3
. You do not have to consider stereochemistry.
• Include only alkenes that will give the alcohol as the single major product.
O
.
Separate structures with + signs from the drop-down menu.
2
IF
13
ChemDoodle
Previous
Chapter 4 Solutions
Organic Chemistry (9th Edition)
Ch. 4.3A - Draw Lewis structures for the following free...Ch. 4.3B - a. Write the propagation steps leading to the...Ch. 4.3C - Prob. 4.3PCh. 4.3C - Prob. 4.4PCh. 4.4 - The following reaction has a value of G =...Ch. 4.4 - Under base-catalyzed conditions two molecules of...Ch. 4.5B - When ethene is mixed with hydrogen in the presence...Ch. 4.5B - For each reaction, estimate whether S for the...Ch. 4.7 - a. Propose a mechanism for the free radical...Ch. 4.7 - a. Using bond-dissociation enthalpies from...
Ch. 4.8 - The reaction of tert-butyl chloride with methanol...Ch. 4.8 - Under certain conditions, the bromination of...Ch. 4.8 - When a small piece of plat num is added to a...Ch. 4.10 - Prob. 4.14PCh. 4.10 - Prob. 4.15PCh. 4.12 - The bromination of methane proceeds through the...Ch. 4.12 - a. Using me BDEs in Table4-2 (page 167 ), compute...Ch. 4.13A - What would be the product ratio in the...Ch. 4.13A - Classify each hydrogen atom in the following...Ch. 4.13B - Use the bond-dissociation enthalpies in Tabte4-2...Ch. 4.13B - Prob. 4.21PCh. 4.13B - Prob. 4.22PCh. 4.14 - a. Compute the heats of reaction for abstraction...Ch. 4.14 - 2,3-Dimethylbutane reacts with bromine in the...Ch. 4.14 - Prob. 4.25PCh. 4.15 - Prob. 4.26PCh. 4.15 - Prob. 4.27PCh. 4.16A - Prob. 4.28PCh. 4.16A - Prob. 4.29PCh. 4.16B - Prob. 4.30PCh. 4.16C - Prob. 4.31PCh. 4.16C - Acetonitrile (CH3C N) is deprotonated by very...Ch. 4.16D - Prob. 4.33PCh. 4 - The following reaction is a common synthesis used...Ch. 4 - Consider the following reaction-energy diagram. a....Ch. 4 - Draw a reaction-energy diagram for a one-step...Ch. 4 - Draw a reaction-energy diagram for a two-step...Ch. 4 - Prob. 4.38SPCh. 4 - Treatment of tert-butyl alcohol with concentrated...Ch. 4 - Label each hydrogen atom in the following...Ch. 4 - Prob. 4.41SPCh. 4 - Prob. 4.42SPCh. 4 - Prob. 4.43SPCh. 4 - Prob. 4.44SPCh. 4 - Prob. 4.45SPCh. 4 - Prob. 4.46SPCh. 4 - For each compound, predict the major product of...Ch. 4 - When exactly 1 mole of methane is mixed with...Ch. 4 - Prob. 4.49SPCh. 4 - Prob. 4.50SPCh. 4 - Prob. 4.51SPCh. 4 - When dichloromethane is treated with strong NaOH,...Ch. 4 - Prob. 4.53SPCh. 4 - When a small amount of iodine is added to a...Ch. 4 - Prob. 4.55SPCh. 4 - When healthy, Earths stratosphere contains a low...Ch. 4 - Prob. 4.57SPCh. 4 - lodination of alkanes using iodine (I2) is usually...
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
- Following is a balanced equation for the allylic bromination of propene. CH2==CHCH3 + Br2 h CH2==CHCH2Br + HBr (a) Calculate the heat of reaction, H 0, for this conversion. (b) Propose a pair of chain propagation steps and show that they add up to the observed stoichiometry. (c) Calculate the H 0 for each chain propagation step and show that they add up to the observed H 0 for the overall reaction.arrow_forwardA certain hydrocarbon had the molecular formula C18H30 and contained two triple bonds. Ozonolysis gave CH₂(CH₂)CO₂H and HO₂CCH₂CH₂CO₂H as the only products. Draw a reasonable structure for this hydrocarbon. Click and drag to start drawing a structure.arrow_forwardCompare the reactivity of BF3 vs BBr3. What happens if to one equivalent of these compounds you add (write equations): 1. 2 equivalents of H2O 2. 1 equivalent of n-PrOH (propanol) 3. 1 equivalent of BCl3arrow_forward
- For each of the questions below, fill in the blank. For those blanks that correspond to products, fill in the major product. For blanks corresponding to starting materials or reagents, fill in the appropriate compounds to give the product in highest yield.arrow_forwardDraw structural formulas for organic products A and B in the window below. CH3 CH3CCH₂CI CH3 ● ● Mg ether // Draw only products having the organic portion of the original alkyl halide. Draw carbon-lithium bonds using the single bond tool. If a structure has a copper-lithium bond, do not draw the lithium. Separate products from different steps using the → sign from the drop-down menu. ? CH3OH A ChemDoodleⓇ B Sn [Farrow_forwardHelpppppppparrow_forward
- The glycerol carbonylation reaction with CO₂ to produce glycerol carbonate (Figure 1) is thermodynamically hindered due to several reasons including the presence of water as a by-product and the stability of CO2 as a co-reactant. Discuss the possible approach to overcome the issues and be able to produce a higher yield of targeted glycerol carbonate. 0 OH 0 Cat. A HO LOH + CO₂ + H₂O HO. Figure 1arrow_forwardUse the following reagent table for the reaction of: cyclohexanol + H2 SO4 → cyclohexene Chemical MW (g/mol). Density (g/mL) mmols used Amount used cyclohexanol 100.16 0.9624 1.50 mL Sulfuric Acid 98.08 1.83 1.00 mL cyclohexene 82.14 Based on your answers in the previous two questions, identify what the Limiting Reagent for the reaction is:arrow_forwardThe alkene shown below is treated sequentially with ozone (O3) and zinc/acetic acid. Draw structural formula(s) for the organic product(s) formed. CH3 CH3CHCHCH=CH2 CH3 My . You do not have to consider stereochemistry. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate multiple products using the + sign from the drop-down menu. *** ChemDoodleⓇ ▼n [F isaarrow_forward
- Draw a structural formula for the major organic product of the reaction shown below. CH3(CH2)5 CH2 + . Consider E/Z stereochemistry of alkenes. • Do not show stereochemistry in other cases. CuLi 2 . • You do not have to explicitly draw H atoms. Do not include organocopper or inorganic ion by-products in your answer.arrow_forwardhw10 #16arrow_forward3. Draw mechanism and energy profile diagram when chlorine reacts with propane. Write a mechanism using half arrows for initiation, propagation and termination steps. Draw an energy profile diagram similar to question #2, two curves for major and minor products. Indicate minor and major products. Which product is more stable and why? Explain is Hammond's postulate?arrow_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
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