Concept explainers
Interpretation:
The structure of carbocation and the products formed on the reaction of iodocyclohexane with water are to be written.
Concept Introduction:
Electrophiles are electron deficient species which has positive or partially positive charge. Lewis acids are electrophiles which accept electron pair.
Nucleophiles are electron rich species which has negative or partially negative charge. Lewis bases are nucleophiles which donate electron pair.
Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.
Nucleophilic substitution reaction is a reaction in which an electron rich nucleophile attacks the positive or partial positive charge of an atom or a group of atoms to replace a leaving group.
The
The
An
The nucleophilic substitutions in which a nucleophile replaces a leaving group are known as
Carbocation is a molecule having a carbon atom bearing three bonds and a positive formal charge.
Carbocation are generally unstable because they do not have eight electrons to satisfy the octet rule.
The order of stability of carbocation is such that the tertiary carbocation is the most stable whereas the primary carbocation is the least stable, and secondary carbocation lies between primary and tertiary carbocations.
If primary carbocation is obtained in product, it rearranges itself to secondary or tertiary carbocation to form more stable product.
If secondary carbocation is obtained in product, it rearranges itself to tertiary carbocation to form more stable product.
The stability of carbocation:
The
In the first step, the alkyl halide ionizes to form a carbocation and halide ion.
In the second step, the nucleophile attacks the carbocation to form the product.
The carbocation is trigonal planar in structure and hence, the nucleophile can attack from both the sides to form two products.
Want to see the full answer?
Check out a sample textbook solutionChapter 6 Solutions
Organic Chemistry
- Practice Problem 7.16 When the compound called isoborneol is heated with 9 M sulfuric acid, the product of the reaction is the compound called camphene and not bornylene, as one might expect. Using models to assist you, write a step-by-step mechanism showing how camphene is formed. HO H,O not heat Isoborneol Camphene Bornylenearrow_forward6.27 Your task is to prepare isopropyl methyl ether by one of the following reactions. Which reaction would give the better yield? Explain your answer. ·l+ (1) This announcement is rinud for comments + CH₂ONa OCH₂ or (2) Isopropyl methyl ether ONa + CH₂l - OCH₂ Isopropyl methyl etherarrow_forward• PRACTICE PROBLEM 8.19 Treating cyclohexene with 1,1-diiodoethane and a zinc-copper couple leads to two isomeric products. What are their structures?arrow_forward
- • PRACTICE PROBLEM 8.12 Treating a hindered alkene such as 2-methyl-2-butene with BH3:THE leads to the for- mation of a dialkylborane instead of a trialkylborane. When 2 mol of 2-methyl-2-butene is added to 1 mol of BH3, the product formed is bis(3-methyl-2-butyl)borane, nicknamed in reagent "disiamylborane." Write its structure. Bis(3-methyl-2-butyl)borane is a useful certain syntheses that require a sterically hindered borane. (The name “disiamyl" comes from "disecondary-iso-amyl," a completely unsystematic and unacceptable name. The name "amyl" is an old common name for a five-carbon alkyl group.) donbyarrow_forward6.24 Sodium nitrite (NaNO2) reacted with 2-iodooctane to give a mixture of two constitutionally isomeric compounds of molecular formula C3 H17NO2 in a combined yield of 88%. Suggest reasonable structures for these two isomers.arrow_forward4.1 9 (a) Define geometric isomerism (b) How does geometric isomerism occur in alkenes? (c) Draw the cis- and trans- geometric isomers (if they exist) of: (i) BrCH=CHBr (ii) CH,CH,CH=CHCH,CH, (iii) Br- CH₂ - CH₂ - Brarrow_forward
- What will be the color of the flame and the amount of soot if the following are ignited:(a) Hexane (b)Heptane(c) Cyclohexane (d) Cyclohexene (e) Benzene (f) Toluenearrow_forwardWrite equations in the synthetic direction for the preparation of 5,6-dicyanobicyclo[2.2.2]oct-2-ene from cyclohexanol and any necessary organic or inorganic reagents.arrow_forwardThe natural product halomon could theoretically arise from another naturally occurring compound known as myrcene. To accomplish this, a biochemical process that could deliver the synthetic equivalent of BrCi to all three double bonds would be required. (Chem Comm. 2014, 50, 13725) (a) Using three molar equivalents of BrCL please provide a mechanism to account for the formation of the bracketed structure (you do not need to show stereochemistry in this mechanism) HB (3 equiv) myrcene balomon 8.61a Add curved arrow(s) to show the mechanism steps. Edit Drawing sitsarrow_forward
- • PRACTICE PROBLEM 8.18 Starting with cyclohexene and using any other needed reagents, outline a synthesis of 7,7-dibromobicyclo[4.1.0]heptane.arrow_forward(a) When bromine is added to two beakers, one containing phenyl iso propyl ether and the other containing cyclohexene, the bromine color in both beakers disappears. What observation could you make while performing this test that would allow you to distinguish the alkene from the aryl ether? (b) Write any three methods in detail for the preparation of aldehyde from primary alcohol. (c) State the clemmenson reduction.arrow_forward(i) Unsolvated methyllithium and tert-butyllithium have similar solid-state structures. Explain the multicentre covalent bonding in these structures. Use diagrams of orbitals where necessary and construct a molecular orbital diagram. (ii) tert-butyllithium is soluble in non-polar alkane solvents but methyllithium is insoluble in non-polar alkane solvents. Explain this observation.arrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY