Connect Access Card Two Year for Organic Chemistry
10th Edition
ISBN: 9781259636868
Author: Francis Carey
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Question
Chapter 10, Problem 38DSP
Interpretation Introduction
Interpretation:
The combination of
Concept Introduction:
Tributyltin hydride is a reducing agent. It converts an alkyl halide to an
This free radical can undergo a reaction with another molecule having a double bond.
The two ends of the double bond are two possible sites of reaction.
The reaction proceeds to form the more stable free radical.
The more stable free radical is the one which is more substituted.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Conversion of an alkene to a halohydrin and internal displacement of a halide ion by an alkoxide ion are both stereoselective. Use this information to demonstrate that the configuration of the alkene is preserved in the epoxide. As an illustration, show that reaction of cis-2-butene by this two-step sequence gives cis-2,3- dimethyloxirane (cis-2-butene oxide).
The Wittig reaction can be used for the synthesis of conjugated dienes as the example below, 1-phenyl-penta-1, 3-diene. Propose two different sets of reagents that could be combined in a Wittig reaction to give 1-phenyl-1,3-pentadiene.
Determine all of the products obtained from the addition of HCl to the 1,3-diene. Once determined, draw a mechanism that accounts for the formation of every product. Then, Identify and account for the formation of the major adduct/or adducts under these conditions assuming that the reaction is conducted under thermodynamic conditions.
Chapter 10 Solutions
Connect Access Card Two Year for Organic Chemistry
Ch. 10.1 - Prob. 1PCh. 10.1 - Prob. 2PCh. 10.2 - Use the data in Table 10.1 to calculate H for the...Ch. 10.3 - Prob. 4PCh. 10.4 - Prob. 5PCh. 10.4 - Prob. 6PCh. 10.4 - Do the arithmetic involved in converting the...Ch. 10.4 - How many constitutionally isomeric...Ch. 10.4 - Prob. 9PCh. 10.5 - Prob. 10P
Ch. 10.5 - Prob. 11PCh. 10.5 - Prob. 12PCh. 10.6 - Prob. 13PCh. 10.7 - Prob. 14PCh. 10.8 - Prob. 15PCh. 10 - Carboncarbon bond dissociation enthalpies have...Ch. 10 - Use the bond dissociation enthalpy data in Table...Ch. 10 - Use the bond dissociation enthalpy data in Table...Ch. 10 - Write the structure of the major organic product...Ch. 10 - Excluding enantiomers, free-radical chlorination...Ch. 10 - Prob. 21PCh. 10 - Prob. 22PCh. 10 - Prob. 23PCh. 10 - Prob. 24PCh. 10 - Compound A (C6H14) gives three different...Ch. 10 - Prob. 26PCh. 10 - Prob. 27PCh. 10 - Prob. 28PCh. 10 - Prob. 29PCh. 10 - Guiding your reasoning by retrosynthetic analysis,...Ch. 10 - (Z)-9-tricosene [(Z)-CH3(CH2)7CH=CH(CH2)12CH3] is...Ch. 10 - Prob. 32PCh. 10 - Prob. 33PCh. 10 - Prob. 34DSPCh. 10 - Prob. 35DSPCh. 10 - Prob. 36DSPCh. 10 - Prob. 37DSPCh. 10 - Prob. 38DSP
Knowledge Booster
Similar questions
- Reaction of -pinene with borane followed by treatment of the resulting trialkylborane with alkaline hydrogen peroxide gives the following alcohol. Of the four possible cis,trans isomers, one is formed in over 85% yield. (a) Draw structural formulas for the four possible cis,trans isomers of the bicyclic alcohol. (b) Which is the structure of the isomer formed in 85% yield? How do you account for its formation? Create a model to help you make this prediction.arrow_forwardTreatment of cyclohexene with iodobenzene under the conditions of the Heck reaction might be expected to give 1-phenylcyclohexene. The exclusive product, however, is 3-phenylcyclohexene. Account for the formation of this product.arrow_forwardLike other electrophiles, carbocations add to alkenes to form new carbocations, which can then undergo substitution or elimination reactions depending on the reaction conditions. With this in mind, consider the following reactions of nerol, a natural product isolated from lemon grass and other plant sources. Treatment of nerol with TsOH forms α-terpineol as the major product, whereas treatment of nerol with chlorosulfonic acid, HSO3Cl, forms a constitutional isomer, α-cyclogeraniol. Write stepwise mechanisms for both processes. Each mechanism involves the addition of an electrophile—a carbocation—to a double bond.arrow_forward
- Like other electrophiles, carbocations add to alkenes to form new carbocations, which can then undergo substitution or elimination reactions depending on the reaction conditions. With this in mind, consider the following reactions of nerol, a natural product isolated from lemon grass and other plant sources. Treatment of nerol with TsOH forms α-terpineol as the major product, whereas treatment of nerol with chlorosulfonic acid, HSO3Cl, forms a constitutional isomer, αcyclogeraniol. Write stepwise mechanisms for both processes. Each mechanism involves the addition of an electrophile— a carbocation—to a double bond.arrow_forwardKepone, aldrin, and chlordane are synthesized from hexachlorocyclopentadiene and other five-membered-ring compounds. Show how these three pesticides are composed of two five-membered rings.arrow_forwardConsidering the elimination reactions, followed by the deprotonation of water, evaluate the following statements.i- Three equivalents of the base are needed to obtain the terminal alkyne.ii- The alkyl dialect is geminal.iii- The speed of obtaining the alkynes depends only on the concentration of the base.iv- Obtaining alkyne from alkyl dialects is accompanied by two successive elimination reactions. In the first elimination reaction it is possible to use NaOH. However, in the second, it requires a very strong base, such as liquid ammonia. It is correct to say that: i and ii, just i and iii, just i and iv, just i, ii and iv, only all except i. naharrow_forward
- Hydrohalogenation of alkenes in the presence of peroxide adds a halide at the vinyl position. Which halide can be used in UV-catalyzed hydrohalogenation reaction in the presence of diethyl ether to obtain alkyl halide. Note: Distillation of the diethyl ether used in the reaction resulted in a violent explosion. * Molecular fluorine, only molecular bromine, only Molecular chlorine only molecular iodine, only Bromine and Molecular Chlorine, only naharrow_forwardThe Friedel-Crafts Alkylation of p-xylene n-propyl bromide can result in an isopropyl as well as n-propyl substitution. A) Write the chemical equation involved in this reaction. B) Which will be the major and minor product? What do you expect will be the ratio of n-propyl to isopropyl substitution for p-xylene?arrow_forward1,3-pentadiene reacts with HBr. When the double bond at the 3-position reacts, the hydrogen attaches to the 4-carbon, thus forming an allylic carbocation with delocalized electrons. This carbocation has another resonance structure. Because there are equal amounts of diene and hydrogen bromide, in which molecule only one of the double bonds reacts. Which of the following correctly describes this new resonance structure? a) It has a double bond between carbons 3 and 4 b) It has a positive charge on carbon 2 c) It has a positive charge on carbon 4 d) It has a double bond between carbons 2 and 3arrow_forward
- we know that ethers, such as diethyl ether and tetrahydrofuran, are quite resistant to the action of dilute acids and require hot concentrated HI or HBr for cleavage. However, acetals in which two ether groups are linked to the same carbon undergo hydrolysis readily, even in dilute aqueous acid. How do you account for this marked difference in chemical reactivity toward dilute aqueous acid between ethers and acetals?arrow_forwardWrite the free radical monosubstituition mechanism for the bromination ofcyclohexane to give 1-bromocyclohexanearrow_forwardIn the dehydrohalogenation of bromocyclodecane, the major product is cis -cyclodecene rather than trans-cyclodecene. Offer an explanation.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