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-EBOOK>I<
- Give the detailed mechanism for the following nitration reaction. Show the contributing resonance structures and the resonance hybrid for the intermediates. HNO,, H,SO, NO2arrow_forward2-bromo-2-methylbutane with sodium methoxide under SN2/E2 conditions substitution product elimination product both substitution and elimination products no productsarrow_forwardThe reaction of (S)-2-bromopentane with potassium cyanide to yield 2-methylpentanenitrile (2-cyanopentane) occurs via a nucleophilic substitution pathway. The reaction is 100% stereospecific.arrow_forward
- The reaction of (S)-2-bromopentane with potassium cyanide to yield 2-methylpentanenitrile (2-cyanopentane) occurs due to a nucleophilic substitution pathway. The reaction is 100% stereospecific. Please explain what this observation tells about the mechanism of the reaction.arrow_forwardWhy do both the following alkenes yield the same product upon reaction with hydrobromic acid? Validate with a reaction mechanism. HBr HBrarrow_forwardThe following nucleophilic substitution occurs with rearrangement as shown below. Suggest a detailed mechanism for the transformation using arrows to detail electron flow. Cl ОН NAOH H2Oarrow_forward
- When treated with NBS, the molecule below can form two different isomers of product. Provide the two products and a mechanism that accounts for the formation of each.arrow_forwardTrimethyl Phosphite reacts with bromomethane to afford the product shown below via a two-step mechanism. Draw a detailed mechanism for this reaction using arrows to show electron flow (both mechanistic steps are SN2 reactions).arrow_forwardImines are electrophiles in the related Mannich reaction. Draw two transition states, one leading to the syn diastereomer and one leading to the anti. Briefly explain which is favoured and why. Assume the imine doesn't change geometry. OM H3G CH3 Ph CH3arrow_forward
- Explain why the following compound does not undergo nucleophilic substitution by either SN1 or SN2 mechanisms. Brarrow_forwardTreatment 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_forwardCompounds X and Y are both C7H15Cl products formed in the radical chlorination of 2,4-dimethylpentane. Base-promoted E2 elimination of X and Y gives, in each case, a single C7H₁4 alkene. Both X and Y undergo an SN2 reaction with sodium iodide in acetone solution to give C7H15l products; in this reaction Y reacts faster than X. What is the structure of X? • Do not use stereobonds in your answer. • In cases where there is more than one possible structure for each molecule, just give one for each. . Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. наarrow_forward
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