Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
expand_more
expand_more
format_list_bulleted
Question
Chapter 13, Problem 2LGP
Interpretation Introduction
Interpretation:
The conversion of
Concept introduction:
▸ The reagent NBS is used for the allylic bromination of the
▸ The dehydrohalogenation of halo alkene takes place in the presence of a base like KOH to form the alkene as a product.
▸ The process in which the alkene is treated with ammonia and oxygen for the formation of nitrile is known as Ammoxidation.
▸ A reaction in which dienes and dienophiles react with each other to form the cyclic compound is known as Diels Alder reaction.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
(a) Cyclohexa-1,3-diene can be converted into a tetrasubstituted haloalkane when reacted with bromine in ether. Write a balanced chemical equation for the reaction that occurs and state the expected observation.
(b) Compound A and B are alkenes with the same molecular formula C5H10. Compound A is a branched-chain alkene while compound B is a straight-chain alkene. The reaction between compound A with hydrogen bromide produces major product C which is optically active.
(i) Draw TWO (2) possible structures for compound B.
(ii) Outline the mechanism for the reaction between compound A with hydrogen bromide to form major product C.
(iii) Name the product formed when compound A undergoes bromination reaction.
Explain why
(i) the dipole moment in chlorobenzene is lower than that of cyclohexyl chloride.
(ii) haloalkanes are only slightly soluble in water but dissolve easily in organic solvents.
Draw structural formulas for the following compounds:
(a) (2Z,4Z)-2,4-dibromo-3-methylhepta-2,4-diene (b) ((2E,4Z)-2-bromo-3,5-dichloro-4-methylhexa-2,4-diene
Chapter 13 Solutions
Organic Chemistry
Ch. 13 - Prob. 1PPCh. 13 - Prob. 2PPCh. 13 - Prob. 3PPCh. 13 - Practice Problem 13.4 From each set of resonance...Ch. 13 - Practice Problem 13.5 The following enol (an...Ch. 13 - Prob. 6PPCh. 13 - Practice Problem 13.7
Two compounds, A and B, have...Ch. 13 - Prob. 8PPCh. 13 - Prob. 9PPCh. 13 - Prob. 10PP
Ch. 13 - Prob. 11PPCh. 13 - Prob. 12PPCh. 13 - Prob. 13PPCh. 13 - Prob. 14PPCh. 13 - Prob. 15PPCh. 13 - Practice Problem 13.16
Diels–Alder reactions also...Ch. 13 - Prob. 17PPCh. 13 - Prob. 18PCh. 13 - What product would you expect from the following...Ch. 13 - Prob. 20PCh. 13 - Prob. 21PCh. 13 - Provide the reagents necessary for each of the...Ch. 13 - Prob. 23PCh. 13 - Prob. 24PCh. 13 - Prob. 25PCh. 13 - When 1-pentene reacts with N-bromosuccinimide...Ch. 13 - Prob. 27PCh. 13 - Prob. 28PCh. 13 - Prob. 29PCh. 13 - Prob. 30PCh. 13 - 13.31 Provide a mechanism that explains formation...Ch. 13 - 13.32 Provide a mechanism that explains formation...Ch. 13 - Treating either 1-chloro-3-methyl-2-butene or...Ch. 13 - Prob. 34PCh. 13 - Prob. 35PCh. 13 - Although both 1-bromobutane and 4-bromo-1-butene...Ch. 13 - Prob. 37PCh. 13 - Prob. 38PCh. 13 - Prob. 39PCh. 13 - Prob. 40PCh. 13 - Prob. 41PCh. 13 - Prob. 42PCh. 13 - Prob. 43PCh. 13 - Prob. 44PCh. 13 - 13.44 When furan and maleimide undergo a...Ch. 13 - Two controversial hard insecticides are aldrin and...Ch. 13 - Prob. 47PCh. 13 - Prob. 48PCh. 13 - Prob. 49PCh. 13 - Prob. 50PCh. 13 - Explain the product distribution below based on...Ch. 13 - Mixing furan (Problem 13.44) with maleic anhydride...Ch. 13 - Prob. 53PCh. 13 - Prob. 54PCh. 13 - Prob. 1LGPCh. 13 - Prob. 2LGPCh. 13 - Prob. 1QCh. 13 - Prob. 2QCh. 13 - Prob. 3QCh. 13 - Prob. 4QCh. 13 - Prob. 5Q
Knowledge Booster
Similar questions
- (1) Predict the outcome of the addition of HBr to (a) trans-2-pentene, (b) 2-methyl-2-butene, and (c) 4-methylcyclohexene. How many isomers can be formed in each case?arrow_forward(3) HI does not undergo free radical addition with 1-butene, even in the presence of a peroxide. Please provide an explanation by analyzing the propagation steps if the same radical reaction occurred with HI. Besides the bond dissociation enthalpies in the appendix, the following approximate bond dissociate enthalpies might be useful to you: ~310 kJ/mol The component of C=C CH3CH₂CH₂CH₂-Br CH3CH₂CH₂CH2-I -290 kJ/mol (C-Br bond) ~235 kJ/mol (C-I bond)arrow_forwardFor each alkane, which mono brominated derivatives could you form in good yield by free-radical bromination?(a) cyclopentane (b) methylcyclopentane(c) 2-methylpentane (d) 2,2,3,3-tetramethylbutanearrow_forward
- Give reasons: (i) C—Cl bond length in chlorobenzene is shorter than C—Cl bond length in CH3—Cl.(ii) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.(iii) SN1 reactions are accompanied by racemization in optically active alkyl halidesarrow_forwardProvide the structure of (Z)-1-chloro-1-fluoro-1-butene.arrow_forwardAcrolein and 1,3-cyclohexadiene react in a one-step concerted manner to yield a single product. Give the structure of the product. What kind of reaction is this an example of? In terms of this reaction, how would you classify acrolein? How would you classify 1,3-cyclohexadiene? Hint: acrolein is not a systematic name so you may need to look up its structure if you are not already familiar with it.arrow_forward
- Write structural formulas for the following:(a) 2,3-Dimethyl-1-cyclobutene(b) 2-Methyl-2-butene(c) 2-Methyl-1,3-butadiene(d) 2,3-Dimethyl-3-ethylhexane(e) 4,5-Diethyloctane(f) Cyclooctene(g) Propadiene(h) 2-pentynearrow_forward(a) Explain how pyrrole is isoelectronic with the cyclopentadienyl anion.(b) Specifically, what is the difference between the cyclopentadienyl anion and pyrrole?(c) Draw resonance forms to show the charge distribution on the pyrrole structure.arrow_forwardThe pentadienyl radical, H2C“CH¬CH“CH¬CH2#, has its unpaired electron delocalized over three carbon atoms.(a) Use resonance forms to show which three carbon atoms bear the unpaired electron.(b) How many MOs are there in the molecular orbital picture of the pentadienyl radical?(c) How many nodes are there in the lowest-energy MO of the pentadienyl system? How many in the highest-energy MO?(d) Draw the MOs of the pentadienyl system in order of increasing energy. (continued)762 CHAPTER 15 Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy(e) Show how many electrons are in each MO for the pentadienyl radical (ground state).(f) Show how your molecular orbital picture agrees with the resonance picture showing delocalization of the unpairedelectron onto three carbon atoms.(g) Remove the highest-energy electron from the pentadienyl radical to give the pentadienyl cation. Which carbon atomsshare the positive charge? Does this picture agree with the resonance picture?(h) Add an…arrow_forward
- (b) (1-chloromethyl)cyclopentane, CeH11CI reacts with aqueous sodium hydroxide, NaOH to produce a primary alcohol AA. When CeH11Cl is added with magnesium, Mg in ether, an organometallic compound BB is formed. When compound BB reacts with ethanal, CH3CHO, a secondary alcohol cCis formed. The molecular structure of CeH11Cl is given below. (1-klorometil)siklopentana, CoH1,CI bertindak balas dengan akues natrium hidroksida, NaOH bagi menghasilkan satu alkohol primer AA. Apabila CeH11CI ditambah dengan magnesium, Mg dalam eter, sebatian organologam BB terbentuk. Apabila sebatian BB bertindak balas dengan etanal, CH;CHO, satu alkohol sekunder CC dihasilkan. Struktur molekul bagi CsH11CI diberikan di bawah. .CI (1-chloromethyl)cyclopentane (i) Draw the structural formula for compound AA through Cc. Lukiskan formula struktur bagi sebatian AA sehingga C. (ii) What is the type of reaction to produce compound AA? Apakah jenis tindak balas untuk menghasilkan sebatian AA?arrow_forwardWrite structural formulas for toluene (C6H5CH3) and for benzoic acid (C6H5CO2H) (a) as resonance hybrids of two Kekulé forms and (b) with the Robinson symbol.arrow_forwardFirst calculate the number if moles of the given compounds.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