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(a)
Interpretation:
Whether the nucleophilic substitution reaction shown, results in three different products that are constitutional isomers of one another, occurs via an
Concept introduction:
An
The carbocation in the first step can rearrange to another one as a result of resonance if adjacent to a double or triple bond. A
An
(b)
Interpretation:
A mechanism that accounts for the formation of each product is to be proposed.
Concept introduction:
An
The carbocation in the first step can rearrange to another one as a result of resonance if adjacent to a double or triple bond. A
An
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Chapter 8 Solutions
EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
- For each reaction, draw the complete mechanism and the major organic product(s), paying attention to stereochemistry. (a) (b) OH LOH (еxcess) ? ? CH,Cl2 CH2CI2arrow_forwardThis addition of HBr to (Z)-2-bromobut-2-ene takes place regioselectively, with the Br preferentially adding to the alkene C that does not already possess a Br atom. (a) Provide a detailed mechanism for this reaction, including initiation and propagation steps. (b) Explain why this regiochemistry is observed. Br Br HBr ROOR Brarrow_forwardFor each pair of compounds determine which will undergo electrophilic substitution faster. (a) (b) (c) (d) CF3 HO Он NO2 () (g) SCH, (e) SO,H OH (h) CI CI HOarrow_forward
- (a) Propose a mechanism for reaction A, which is a substitution reaction. (b) Explain why reaction B does not lead to a similar substitution.arrow_forwardMany primary amines, RNH2, where R is a carboncontainingfragment such as CH3, CH3CH2, and so on,undergo reactions where the transition state is tetrahedral.(a) Draw a hybrid orbital picture to visualize thebonding at the nitrogen in a primary amine (just use a Catom for “R”). (b) What kind of reactant with a primaryamine can produce a tetrahedral intermediate?arrow_forwardPredict the product for the reaction between m-ethylbenzoyl chloride (see Problem 20.35) and each of the following. Draw the complete, detailed mechanism for each reaction. If no reaction is expected to occur, write “no reaction." (a) (CH3CH2)2CuLi; (b) LİAIH(O-t-Bu)3, – 78 °C; (c) NaBH4, EtOH; (d) C6H5MgBr (excess), then H*arrow_forward
- Draw the appropriate curved arrows and products for each set of reactants undergoing a coordination step. Identify each reactant species as a nucleophile or electrophile. (a) NH₂ + AICI, →? (b) H₂O + BF₂? (c) ³0° H₂C OH - >?arrow_forward(b) Show the mechanism of this reaction using proper arrow push notation. You must show all intermediates, formal charges, and necessary arrows. CH3 CH3 CH3 H20 H2SO4arrow_forwardfor each reaction, provide the likely product and the mechanism.arrow_forward
- When ethylbenzene reacts with bromine in a free radical halogenation, a small amount ofproduct that contains no bromine is formed. Show the mechanism of how the product isformed and the product. Explain why only a small amount of that product is formed.arrow_forwardEach of the following may participate in an elimination reaction, under the proper conditions. (a) Circle the alpha (a) carbon. (b) Circle the beta (B) carbon(s). (c) Draw the alkene product(s) that may form, with the new double bond between the a and ß positions. (d) If more than one alkene product is possible, circle the most stable (Zaitsev) product. A В J C K E F G 33-0arrow_forwardThe following reaction, which is discussed in Chapter 8, is an example of a unimolecular nucleophilic substitution (Sn1) reaction. It consists of the four elementary steps shown here. For each step (i-iv), (a) identify all electron-rich sites and all electron-poor sites, (b) draw in the appropriate curved arrows to show the bond formation and bond breaking that occur, and (c) name the elementary step. (i) H-OCH3 OH + H-OCH3 H. H (ii) ©CH2 + H,O (iii) ©CH2 CH3 + HO-CH3 (iv) CH3 CH3 + H2O-CH, + НО—СНЗ foarrow_forward
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