Concept explainers
(a)
Interpretation:
How to carry out the given transformation which may require more than one reaction is to be shown.
Concept introduction:
Usually secondary and tertiary alcohols show dehydration reaction through E1 mechanism. In presence of any strong acid, the dehydration of alcohols occurs. In step one, the strong acid protonates the hydroxyl oxygen atom and converts it to a good leaving group. In the next step, the leaving group leaves resulting in the formation of a carbocation intermediate. The carbocation intermediate which is formed can rearrange itself via 1, 2-hydride shift or 1, 2-methyl shift to yield a more stable carbocation. Third step is a deprotonation step in which water removes the proton which is adjacent to the carbocation and forms the most substituted
(b)
Interpretation:
How to carry out the given transformation requiring more than one reaction is to be shown.
Concept introduction:
Alcohols can be converted to least substituted alkene via Hoffman elimination. Hoffman elimination requires an amine precursor which can be generated from the starting alcohol after using
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Chapter 10 Solutions
ORGANIC CHEMISTRY PRINCIPLES & MECHANISM
- (SYN) Show two different syntheses for the compound shown here, one using (CH3)2CULI as a reagent and the other using (CH3CH2)2CuLi.arrow_forwardDraw the complete, detailed E1 mechanism for each of the following reactions, and show all resonance structures, where applicable.arrow_forward(SYN) Propose how you would carry out the transformation shown here. Hint: It may take more than a single reaction. OH OH ? + Enantiomer Br ОНarrow_forward
- The reaction shown here is an example of the Favorskii reaction, which involves an R¯ leaving group in a nucleophilic addition-elimination reaction. (a) Draw the complete, detailed mechanism for this reaction and explain why R can act as a leaving NaOH H2O group. (b) Suggest how you can synthesize an ester from cyclopropanone using only this reaction.arrow_forward(SYN) Show how to carry out each of the following transformations. (a) (b) ? ? OH CIarrow_forward(SYN) Show how to carry out each of the following syntheses, using any reagents necessary. Hint: In each case, the carbonyl group of a ketone or aldehyde is entirely removed. (a) (b) ? OCH3 OCH3 OCH3 OCH3 (c) (d) ? ? OH Pharrow_forward
- Textbook problem: Suggest short series of reactions that would be expected to transform the material on the right into the desired product shown on left.arrow_forwardBonus Question: If you deemed the previous reaction to be unsuccessfull, propose a reaction or synthesis that would successfully produce the desired ether product (shown again to the side). You may use any reaction you know of.arrow_forwardPlease draw a detailed mechanism for all steps in the following reaction sequence. Please clearly show electron movement.arrow_forward
- Draw a detailed mechanism for the following reaction and include the major productarrow_forward(SYN) For each of these compounds, draw an alkyl (a) (b) halide that can be used to produce it in an E1 reaction. Then, draw the E1 mechanism that would take place when the alkyl halide is treated with water.arrow_forwardProblem: Consider the reaction sequence shown below. Pay attention to stereochemistry. (a) Draw the structure for compound A and explain your reasoning. (b) Draw the structure for compound B and explain your reasoning. (c) Draw the structure for compound C and explain your reasoning. он Conc. H,PO, MCPBA A NaCN MeOHarrow_forward
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