Concept explainers
Interpretation:
The reason has to be explained for the given compound does not undergo a nucleophilic substitution reaction by either SN1 or SN2 mechanisms.
Concept introduction:
SN1 reaction:
The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.
Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation. Primary alcohol is less stable therefore it won’t undergo SN1 substitution reaction.
SN2 reaction:
Tosylated compound is reaction with sodium methoxide which undergoes again SN2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,
Given information:
The given compound is shown below,
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Chapter 11 Solutions
Organic Chemistry
- Treatment of a cyclic ketone with diazomethane is a method for accomplishing a ring-expansion reaction. The reaction involves the initial nucleophilic attack by diazomethane on the carbonyl carbon to form a tetrahedral intermediate. Collapse of this intermediate is accompanied by bond migration and loss of N,. For example, treatment of cyclohexanone with diazomethane yields cycloheptanone. CH2N2, ether + N2 Draw the structure of the organic product(s) of the ring expansion of this compound: • 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. • Draw one structure per sketcher Add additional ketchers usina the dron down menu in the bottom right co Previous Nextarrow_forwardFor each reaction, give the expected substitution product, and predict whether the mechanism will be predominantly first order (SN1) or second-order (SN2). (a) isobutyl bromide + sodium methoxidearrow_forwardIllustrate the resonance effect of the methoxy group -OCH3, on the structure of the benzene ring. Draw all the oissuvke resonance forms of methoxybenzene, including the hybrid Based on the structures, explain how the presence of the -OCH3 group affects: (i) the reactivity of the benzene ring towards electrophilic attack (ii) the orientation or point of attack of an incoming electrophilic reagent on the benzene ring.arrow_forward
- Show how to synthesize each of the following compounds using only a single nucleophilic aromatic substitution reaction. (a) NO, (b) (c) NO2 O,N ноarrow_forwardFor each reaction, give the expected substitution product, and predict whether the mechanism will be predominantly first order (SN1) or second-order (SN2). (a) cyclohexyl bromide + sodium ethoxidearrow_forwardFor each reaction, give the expected substitution product, and predict whether the mechanism will be predominantly first order (SN1) or second order (SN2). (a) cyclohexyl bromide + methanolarrow_forward
- Which of the following is expected to be most reactive towards a nucleophilic aromatic substitution via the addition-elimination mechanism? LOCH3 LOCH3 A) B) ZON O2N OCH3 D) LOCH3 NO2 NO2 F A В O Darrow_forwardAcid-catalyzed bromination of pentan-2-one (CH3COCH2CH2CH3) forms two products: BrCH2COCH2CH2CH3 (A)and CH3COCH(Br)CH2CH3 (B). Explain why the major product is B, with the Br atom on the more substituted side of the carbonyl group.arrow_forward(b) Predict the major product (or products) formed when each of the following compounds 11- 14 reacts with a mixture of concentrated HNO3 and H2SO4. CO2H HN CO2H CI 11 12 13 14 (c) Pick one of the reactions under (b) and write the mechanism of the electrophilic aromatic substitution in detail (generation of the attacking electrophile is not required).arrow_forward
- Which of the following would be a better starting material for a nucleophilic aromatic substitution reaction? Explain your choice using structures. Then provide the complete arrow pushing mechanism for the reaction of the better starting material and excess ethanol. CI CI O₂N NO₂ NO₂ NO₂arrow_forwardPlease give the main substitution product for each of the following reactions, and indicate the dominant mechanism: (a) 1-bromopropane + NaOCH3 → (b) 3-bromo-3-methylpentane + NaOC2H5 →arrow_forwardQ1) Name the following compounds according to IUPAC system: OH OH Br NH2 NO2 CH2CH2CH3 Br Q2) complete the following reactions: NO2 Cl2 AICI 3 CH2CH2CH3 KMnO4 Q3) Decide whether the following benzene rings are activated (have ortho-para directing groups) or deactivated (have meta directing groups) towards electrophilic aromatic substitution reactions: LOH CNarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning