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Concept explainers
Interpretation:
The products formed on the methanolysis of iodocyclohexane derivative are to be determined.
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
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 carbocation is trigonal planar in structure and hence, the nucleophile can attack from either of the sides to form two products.
Solvolysis is the nucleophilic substitution of solvent molecules. Methanolysis is the reaction of an alkyl halide with methanol.
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Chapter 6 Solutions
Organic Chemistry
- PRACTICE PROBLEM 6.5 Using chair conformational structures (SectionA), show the nueleophilie substitution reaction that would take place when trans-1-bromo-4-tert-butyleyclohexane reacts with lodide lon. (Show the most stable conformnation of the reactant and the product.) Sy2 reactions always occur with inversion of configurationarrow_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_forward10.23 Show, by writing a suitable sequence of chemical equations, how you could prepare the following compound from cyclopentene and any necessary organic or inorganic reagents: (a) 2-Cyclopenten-1-olarrow_forward
- 8.30 Outline an efficient synthesis of each of the following compounds from the indicated start- ing material and any necessary organic or inorganic reagents: (a) Cyclopentyl cyanide from cyclopentane (b) Cyclopentyl cyanide from cyclopentene (c) Cyclopentyl cyanide from cyclopentanol (d) NCCH₂CH₂CN from ethyl alcohol (e) Isobutyl iodide from isobutyl chloride (f) Isobutyl iodide from tert-butyl chloride (g) Isopropyl azide from isopropyl alcohol (h) Isopropyl azide from 1-propanol (i) (S)-sec-Butyl azide from (R)-sec-butyl alcohol (i) (S)-CH3CH₂CHCH3 from (R)-sec-butyl alcohol SHarrow_forward13. (18 pts) Spiropentane, shown on the left, reacts with Cl2 in the presence of light to furnish the two products shown on the right. Given that Cl2 is readily cleaved by light, provide a detailed step-by-step mechanism for the formation of the two products from the common intermediate shown in brackets, and also show the mechanism for the formation of the common intermediate from spiropentane. Use curved arrows to detail electron flow. Cl Cl2 Cl Cl hv Cl Clarrow_forward• PRACTICE PROBLEM 6.6 S 2 reactions that involve substitution at a chirality center can be used to relate the configuration of one molecule to another, because we know the SN2 reaction will occur with inversion. (a) Illustrate how this is true by assigning R,S configurations to the 2-chlorobutane enantiomers based on the following data. [The configuration of (-)-2-butanol is given in Section 5.8C.] HO- (+)-2-Chlorobutane (-)-2-Butanol SN2 [a]3 = +36.00 (Enantiomerically pure) [a] = -13.52 (Enantiomerically pure) noin (b) When enantiomerically pure (+)-2-chlorobutane is allowed to react with potassium iodide in acetone in an SN2 reaction, the 2-iodobutane that is produced has a minus optical rotation. What is the configuration of (-)-2-iodobutane? Of (+)-2-iodobutane?arrow_forward
- • PRACTICE PROBLEM 8.6 Write a mechanism that shows how 2,3-dimethyl-2-butanol is formed in the acid- catalyzed hydration of 3,3-dimethyl-1-butene.arrow_forwardProblem 6.4 Suggest a reasonable biosynthetic pathway to (i) trans citral 6.1 and (ii) the aggregation pheromone 6.41 of the Colorado beetle from geranyl pyrophosphate 6.40. OH HO. 6.41arrow_forward8.30 Outline an efficient synthesis of each of the following compounds from the indicated starting material and any necessary organic or inorganic reagents: (d) NCCH2CH2CN from ethyl alcohol (e) Isobutyl iodide from isobutyl chloride (f) Isobutyl iodine from tert-butyl chloridearrow_forward
- 5.34 Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. (a) 1-Butanol or 2-butanol (b) 2-Methyl-1-butanol or 2-butanol (c) 2-Methyl-2-butanol or 2-butanol (d) 2-Methylbutane or 2-butanol dovolonentanol or cyclohexanolarrow_forward10.16 Design a preparation of each of the following compounds from an alcohol using sulfonate ester methodology. (a) (b) -CH,CH,CH,– SCH, 10.21 (a) According to the mechanism of the reaction shown in Eq. 10.34, what would be the absolute configuration of the alkyl chloride obtained from the reaction of thionyl chloride with (S)-CH,CH,CH,CHD-OH? Explain. (b) According to the mechanism shown in Eqs, 10,36a and 10.36b, what would be the absolute configuration of 2-bromopentane obtained from the reaction of Ph,PBr, with the R enantiomer of 2-pentanol? Explain.arrow_forward• PRACTICE PROBLEM 8.13 Specify the appropriate alkene and reagents for synthesis of each of the following alcohols by hydroboration–oxidation. (a) (c) OH (e) CH3 OH AH OH no mobe OH ( (b) (d) (f) OH HT H3 D OH OH HO OHarrow_forward
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