Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 8.5, Problem 9P
Interpretation Introduction
a)
Interpretation:
The structure of the product obtained by the hydroboration-oxidation of 2-methyl-2-pentene is to be given.
Concept introduction:
The hydroboration reaction takes place with syn stereochemistry and results in a non-Markovnikov addition of water to the double bond in an
To give:
The structure of the product obtained by the hydroboration-oxidation of 2-methyl-2-pentene.
Interpretation Introduction
b)
Interpretation:
The structure of the product obtained by the hydroboration-oxidation of the compound is to be given.
Concept introduction:
The hydroboration reaction takes place with syn stereochemistry and results in a non-Markovnikov addition of water to the double bond in the alkene. The resulting product has the hydroxyl group on the less highly substituted carbon.
To give:
The structure of the product obtained by the hydroboration-oxidation of the compound shown.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Draw the organic product obtained by hydroboration-oxidation of each of the following alkenes: (a) trans-2-pentene, (b) 2-tert-butyl-3,3-dimethyl-1-
butene, and (c) 1-methylcyclohexene. Having done this, draw the product of the acid-catalyzed hydration of these same alkenes. How do the
reaction products differ?
Na, NH3
H3C-C=C-CH3
CH3
H3C°
Alkynes are reduced to trans alkenes by a process called dissolving metal reduction. The reaction uses sodium or lithium metal as the reducing agent and liquid ammonia as the solvent. The
method is specific in the formation of trans alkenes from alkynes. The method involves two successive transfers of single electrons from the alkali metal to the triple bond, with abstraction of
protons from the ammonia solvent.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
.CH3 H-NH2
CH3
:NH2
H3C
H3C
If the following reaction were carried out, how many isomeric alkene products would be possible?
(I'm looking for the total number possible, not an evaluation of which of them is most likely to be
formed.)
Br
CH3CH20
+
O 3
O 0
O 2
O 4
O 1
Chapter 8 Solutions
Organic Chemistry
Ch. 8.1 - Prob. 1PCh. 8.1 - How many alkene products, including E,Z isomers,...Ch. 8.2 - Prob. 3PCh. 8.2 - Addition of HCl to 1, 2-dimethylcyclohexene yields...Ch. 8.3 - Prob. 5PCh. 8.3 - Prob. 6PCh. 8.4 - Prob. 7PCh. 8.4 - From what alkenes might the following alcohols...Ch. 8.5 - Prob. 9PCh. 8.5 - What alkenes might be used to prepare the...
Ch. 8.5 - Tho following cycloalkene gives a mixture of two...Ch. 8.6 - Prob. 12PCh. 8.7 - Prob. 13PCh. 8.7 - Starting with an alkene, how would you prepare...Ch. 8.8 - Prob. 15PCh. 8.8 - Prob. 16PCh. 8.9 - What products would you expect from the following...Ch. 8.10 - Prob. 18PCh. 8.10 - Prob. 19PCh. 8.13 - Prob. 20PCh. 8.13 - What products are formed from hydration of...Ch. 8.SE - Name the following alkenes, and predict the...Ch. 8.SE - Prob. 23VCCh. 8.SE - Prob. 24VCCh. 8.SE - Prob. 25VCCh. 8.SE - Prob. 26MPCh. 8.SE - Prob. 27MPCh. 8.SE - Draw the structures of the organoboranes formed...Ch. 8.SE - Prob. 29MPCh. 8.SE - Provide the mechanism and products for the...Ch. 8.SE - Propose a curved-arrow mechanism to show how ozone...Ch. 8.SE - Prob. 32MPCh. 8.SE - Prob. 33MPCh. 8.SE - Prob. 34MPCh. 8.SE - 10-Bromo- α -chamigrene, a compound isolated from...Ch. 8.SE - Isolated from marine algae, prelaureatin is...Ch. 8.SE - Dichlorocarbene can be generated by heating sodium...Ch. 8.SE - Reaction of cyclohexene with mercury(II) acetate...Ch. 8.SE - Use your general knowledge of alkene chemistry to...Ch. 8.SE - Prob. 40MPCh. 8.SE - Hydroboration of 2-methyl-2-pentene at 25°C,...Ch. 8.SE - Prob. 42APCh. 8.SE - Suggest structures for alkenes that give the...Ch. 8.SE - Prob. 44APCh. 8.SE - Prob. 45APCh. 8.SE - Prob. 46APCh. 8.SE - Prob. 47APCh. 8.SE - Predict the products of the following reactions....Ch. 8.SE - Prob. 49APCh. 8.SE - How would you carry out the following...Ch. 8.SE - Draw the structure of an alkene that yields only...Ch. 8.SE - Show the structures of alkenes that give the...Ch. 8.SE - Prob. 53APCh. 8.SE - Which of the following alcohols could not be made...Ch. 8.SE - Prob. 55APCh. 8.SE - Prob. 56APCh. 8.SE - Prob. 57APCh. 8.SE - Compound A has the formula C10HI6. On catalytic...Ch. 8.SE - Prob. 59APCh. 8.SE - Prob. 60APCh. 8.SE - Prob. 61APCh. 8.SE - Draw the structure of a hydrocarbon that absorbs 2...Ch. 8.SE - Prob. 63APCh. 8.SE - The sex attractant of the common housefly is a...Ch. 8.SE - Prob. 65APCh. 8.SE - Prob. 66APCh. 8.SE - α-Terpinene, C10H16, is a pleasant-smelling...Ch. 8.SE - Prob. 68APCh. 8.SE - Prob. 69APCh. 8.SE - Prob. 70APCh. 8.SE - Prob. 71APCh. 8.SE - Prob. 72AP
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
- Draw the structures of two alkenes that would react to form the haloalkane below upon addition of HBr. Your alkenes should be different regioisomers that yield the haloalkane as the major product without requiring rearrangement to occur.arrow_forwardYou are required to synthesize 2-bromopentane from the reaction between an alkene with HBr. Which alkene, 1-pentene or 2-pentene, should you react with HBr in order to get 2-bromopentane? Give an explanation.arrow_forwardHydroxylation of E-2-pentene with osmium tetroxide yields a different product than the same reaction using the Z configuration. Draw the structures of the alkenes and show the stereochemistry for each product. Explain any differences between them.arrow_forward
- Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions -X티 Hö: H-O -CH3 -CH3 H30*arrow_forwardCCH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Hjö: -CH3 -CH3 H3O*arrow_forwardSuppose that the alkene in Figure 9 reacts with 1 mole of hydrogen chloride. Predict the structure of the main product of the reaction.arrow_forward
- C=CH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H-OH HO: Hjö: C=CH c=CH Hö Hg Hgarrow_forwardEthers can be prepared by reaction of an alkoxide or phenoxide ion with a primary alkyl halide. Draw the structure of the expected organic product of the reaction of iodomethane with the following alkoxide ion: CH3 H3C O Na You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Do not include counter-ions, e.g., Na", I, in your answer. орy вste ChemDoodlearrow_forwardFor each of the following alkenes, assign the configuration of the double bond as either Z or E:arrow_forward
- 22. Calculate the percent atom economy for the following hydroboration-oxidation reaction. This is another method of hydration of an alkene. Be careful with stoichiometry! You must multiply molecular weights by their stoichiometric coefficients. ОН 3 3 + BH3 +Na;BO3 + 3 H20 +3 H2O2 +3 NaOHarrow_forwardTwo substitution products result from the reaction between 3-chloro-3-methyl-1- butene with sodium acetate (CH3COO – Na +) in acetic acid under SN1. Identify the products.arrow_forwardElimination of HBr from 2-bromobutane affords a mixture of 1-butene and 2-butene. With sodium ethoxide as base, 2-butene constitutes 81% of the alkene products, but with potassium tert-butoxide, 2-butene constitutes only 67% of the alkene products. Offer an explanation for this difference.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Macroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole