Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 8, Problem 8.19P
Interpretation Introduction
Interpretation:
The fraction of each monofluoro product formed in the fluorination of 2-methylbutane has to be estimated.
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1. Consider the following reaction - Dehydrogenation of Methyl Cyclohexane (MCH) to Toluene
(TOL) using a Precious Metal (Pt) supported on Alumina.
CH3
CH3
2
()
+ 3 H₂
Typically, hydrogenation of a cyclo-alkane, like MCH, occurs in 3 or more stages, where one
bond is dehydrogenated per stage, eventually resulting in the dehydrogenation of 3 bonds.
Strong adsorption of MCH is likely to occur, but the adsorption of hydrogen (either as a
molecule on a single site OR as an atom on a single site) is unclear. Therefore, in this
question, two types of reaction mechanisms are to be considered, as discussed below:
(a) You are to first propose a reaction mechanism which includes adsorption, surface reaction,
and desorption. For each of the following cases, please write down a full set of elementary
reaction mechanisms.
(0)
Extraction of Hydrogen in 3 stages, based on dehydrogenation of each bond-where
the ensuing hydrogen product is adsorbed as a molecule on a single site, in one
step.…
Why is less energy required to break a C-H bond to form a more highly substituted radical? Can somebody summarize the words on this page to make it more understandable?
(a)
• All hydrogen atoms are implied.
• You do not have to consider stereochemistry.
• Omit lone pairs and radical electrons from your answer.
3-ethyl-3-pentanol
Draw the structure of the alkene that was used to prepare the alcohol in highest yield.
-8)
O
GA
+
H₂C
*
Cat
CH₂
?
ChemDoodle
Which process does this employ?
01. Hg(OAc)2, H₂O; 2. NaBH4
01. BH3; 2. H₂O2, NaOH
OOSO4, H₂O2
Y
Chapter 8 Solutions
Organic Chemistry
Ch. 8.2 - Prob. 8.1PCh. 8.4 - Name and draw structural formulas for all...Ch. 8.4 - Using the table of bond dissociation enthalpies in...Ch. 8.5 - Prob. 8.4PCh. 8.6 - Given the solution to Example 8.5, predict the...Ch. 8.7 - Prob. 8.6PCh. 8.7 - Linoleic acid is shown below. What makes this...Ch. 8.7 - Prob. BQCh. 8.7 - Prob. CQCh. 8.7 - The strength of the HO bond in vitamin E is weaker...
Ch. 8.7 - Prob. EQCh. 8.8 - Prob. 8.7PCh. 8 - Prob. 8.8PCh. 8 - Prob. 8.9PCh. 8 - Prob. 8.10PCh. 8 - Prob. 8.11PCh. 8 - Account for the fact that among the chlorinated...Ch. 8 - Name and draw structural formulas for all possible...Ch. 8 - Prob. 8.14PCh. 8 - There are three constitutional isomers with the...Ch. 8 - Following is a balanced equation for bromination...Ch. 8 - Prob. 8.17PCh. 8 - Prob. 8.18PCh. 8 - Prob. 8.19PCh. 8 - Cyclobutane reacts with bromine to give...Ch. 8 - Prob. 8.21PCh. 8 - Following is a balanced equation for the allylic...Ch. 8 - Prob. 8.23PCh. 8 - Prob. 8.24PCh. 8 - The major product formed when methylenecyclohexane...Ch. 8 - Prob. 8.26PCh. 8 - Prob. 8.27PCh. 8 - Prob. 8.28PCh. 8 - Write the products of the following sequences of...Ch. 8 - Using your reaction roadmap as a guide, show...Ch. 8 - Prob. 8.31PCh. 8 - Prob. 8.32PCh. 8 - Prob. 8.33PCh. 8 - Prob. 8.34P
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- Free radical halogenation is used to replace one or more hydrogens on an alkane with one or more halogens (either chlorine or bromine). It is a substitution reaction. A student performs a free radical bromination on 3-methyl-pentane (5.88 g) to create the desired product of 3-bromo-3-methyl-pentane. The product mix, which hopefully contains almost all 3-bromo-3-methyl-pentane, is cleaned up by passing it through a gas chromoatograph, which separates out the 3-bromo-3-methyl-pentane from any undesired products made during the reaction (undesired products are created frequently in free radical halogenation). The initial product mix weighed 9.45 g; the purified 3-bromo-3-methyl-pentane weighed 7.21 g. What is the student's percent recovery?arrow_forwardUsing reactions, mechanisms, potential energy diagrams, labels, complete sentences, and the associated concepts, explain the following reaction rate trend for the hydrochlorination of alkenes (the addition of HCI). You may assume: 1) the alkenes are all the same higher energy; and, 2) the chloroalkane products are all the same energy; and, 3) the chloroalkane products are lower in energy than the starting alkenes (AGºrx is negative for each reaction).arrow_forward12. Which of the following carbocations is the least stable one? 13. The heats of complete hydrogenation of the following three hydrocarbons are 105, 116, 275 and 292 (in kJ/mol). Which hydrocarbon does feature the heat of hydrogenation of 292 kJ/mol?arrow_forward
- 3. Please draw the most important (stable) resonance form of the carbonation that mediates the following reaction: OH H3O+ O 4. Draw the structure of the alkene isomer (with the molecular formula of C5H10) that is most reactive one in the addition reaction with Br₂.arrow_forward2-methyl-2-hexanol was prepared by reacting an alkene with either hydroboration-oxidation or oxymercuration-reduction. Draw the structure of the alkene that was used to prepare the alcohol in highest yield. • You do not have to consider stereochemistry. • Indicate the method of preparation by drawing either BH3 (for hydroboration-oxidation), or Hg (for oxymercuration-reduction), in a separate sketcher. • If there is more than one alkene that can be used for a given method, draw all of them. • If either hydroboration-oxidation or oxymercuration-reduction can be used, just give the structures for one method. • Separate structures with + signs from the drop-down menu. *9⁹-85 ? ChemDoodle Sn [Farrow_forwardUsing Zaitsev's rule, choose the most stable alkene among the following. Draw out the structures of each of the options then select the correct answer. Recall that Zaitsev's Rule is about alkene stability. The trend for this is similar to the trend for carbocation stability. Either more or fewer groups on the alkene (and the carbocation) make it more stable. This question is wanting you to remember if it's more or fewer. A) 1,2-dimethylcyclohexene B) 1,6-dimethylcyclohexene C) cis-3,4-dimethylcyclohexene D) They are all of equal stability according to Zaitsev's rule. Provide the major dehydration product of the following reaction. Recall which of the four substitution and elimination reactions a dehydration is. Before you do your S# or EF mechanism, remember what heteroatoms do in the presence of an acid (aka-the-OH is a bad leaving group, but protonating it might turn it into a good one). Don't forget to apply the concept from the previous question. OH Ht Aarrow_forward
- Explain the role strain plays on stability and reactivity of a cyclic alkane such as cyclopropane.arrow_forwardWrite the structure of the product that may result from the dehydrobromination of 2, 3-dimethyl-3-bromopentane. Indicate the major product.arrow_forwardThe compound below is treated with chlorine in the presence of light. CH3 CH3CHCH₂CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. n [ ]# ?arrow_forward
- 7. The reaction of the organoborane intermediate in the anti-Markovnikov hydration of an alkene is said to be an oxidation. The hydration of alkenes is said to be a reduction. What does this mean in terms of the total number of electrons of the alkene reactants?arrow_forward∆H° values obtained for a series of similar reactions are one set of experimental data used to determine the relative stability of alkenes. Explain how the following data suggest that cis-but-2-ene is more stable than but-1-ene (Section 12.3A).arrow_forward4-methyl-3-hexanol was prepared by reacting an alkene with either hydroboration-oxidation or oxymercuration-reduction. Draw the structure of the alkene that was used to prepare the alcohol in highest yield. • You do not have to consider stereochemistry. • Indicate the method of preparation by drawing either BH3 (for . If there is more than one alkene that can be used for a given method, draw all of them. If either hydroboration-oxidation or oxymercuration-reduction can be used, just give the structures for one method. Separate structures with + signs from the drop-down menu. ● 981 -- 26224 ? ChemDoodle Y hydroboration-oxidation), or Hg (for oxymercuration-reduction), in a separate sketcher. Sn [1arrow_forward
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