Interpretation:
The resonance structure of para-intermediate drawn and the relative stability is to be noted.
Concept introduction:
The monosubstituted benzene shows electrophilic
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Organic Chemistry: Principles and Mechanisms (Second Edition)
- In the Wittig reaction, the cyclic gxaphosphetane intermediate (shown below) undergoes fragmentation to produce an olefin and a phosphine oxide. Hypothetically, two possible arrow pushing mechanisms can be proposed but only one is correct. Please select one (mechanism 1 or mechanism 2) and explain why it is correct. If you believe both are correct, also explain why. Ph Ph. Ph Ph Ph Ph mechanism 1 mechanism 2 Ph + Ph Pharrow_forwardIn each reaction box, place the best reagent and conditions from the list. 1) CEN 2) 3) 4) 5) Answer Bank NANH, NaBH, acetone CH,CH, MgBr (excess) acetic acid acetate ion CH,OH, H,O* (cat.) LIAIH, (CH,),CHMgBr (excess) CH,MgBr (excess) H,0 H,0*, H,0, heat acetyl chloridearrow_forwardFor the substrate below write all possible reactions. Ethanol is a weak nucleophile. Please verify whether a hydride shift is possible. + CH3CH2OHarrow_forward
- Chemistry Show retro-synthetic analysis leading from the target molecule to the precursor molecule showing all intermediate molecules.Using organic chemistry from your textbook show an efficient synthesis of your target molecule starting from its parent molecule and showing the structure of each isolable intermediate.Assume you have access to usual reagents like Br2, AlCl3, Fe, HBr, HNO3, H2SO4, etc.Assume that each intermediate can be purified from other products at each step of the synthesis.arrow_forwardThe sodium iodide test is used to identify primary alkyl halides and it also takes place via a substitution reaction.Describe the test including the reactions that explain the full mechanism. Explain whether this reaction follows aSN1 or a SN2 mechanism.arrow_forwardAlcohols are acidic in nature. Therefore, a strong base can abstract the acidic hydrogen atom of the alcohol in a process known as deprotonation. The alcohol forms an alkoxide ion by losing the proton attached to the oxygen atom of the hydroxyl ( -OH) group. The alkoxide formed can act as a base or a nucleophile depending on the substrate and reaction conditions. However, not all bases can abstract the acidic proton of alcohols and not all alcohols easily lose the proton. Deprotonation depends on the strength of the base and the acidity of the alcohol. Strong bases, such as NaNH2, can easily abstract a proton from almost all alcohols. Likewise, more acidic alcohols lose a proton more easily. Determine which of the following reactions would undergo deprotonation based on the strength of the base and the acidity of the alcohol. Check all that apply. ► View Available Hint(s) CH3CH,OH + NH3 →CH,CH,O-NH CH3 CH3 H3C-C-H+NH3 → H3 C-C-H OH O-NH CH3CH2OH + NaNH, → CH3CH,O-Na* + NH3 CHC12 Cl₂…arrow_forward
- Complete the electron-pushing mechanism for the reaction of the y-hydroxyaldehyde in hydrochloric acid by adding any missing atoms, bonds, charges, nonbonding electrons, and curved arrows. Note the use of a generic alcohol representing another alcohol molecule in solution. Step 1: draw curved arrows. Step 2: complete the structure and add curved arrows. Select Draw Rings Groups More Erase Select Draw Rings Groups More Erase R -0 : H. | H H 1Larrow_forwardNot all functional groups are compatible with Grignard reagents. Classify each proposed Grignard reagent as a feasible or an unfeasible Grignard reagent. -MgBr BrCH₂CH₂CH₂ MgBr Feasible CH₂CH₂CH₂CH₂ MgBr MgBr Answer Bank phenylMgBr HOCH₂CH₂ MgBr Unfeasible H₂C=CHCH₂MgBr HOOC–CH,CH,MgBrarrow_forwardThe Stille coupling reaction is another metal-catalyzed reaction that is a great way to form carbon-carbon bonds. What makes the Stille coupling unique is that it is a carbonylative reaction, meaning CO is inserted into the compound to make a carbonyl group. The mechanism involves oxidative addition, coordination, insertion, transmetallation, and reductive elimination. Suggest a mechanism for the following Stille coupling. OTf Me Si SnBu3 cat. Pd(PH3)4 LICI, 1.1 atm CO C12H20OSIarrow_forward
- Draw the major 1,2- and 1,4-addition products obtained in the reaction shown. Assume that both are derived from the most stable carbocation intermediate. + HCI • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • If the 1,2- and 1,4- addition products are the same due to symmetry, only draw one structure. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. ● Separate multiple products using the + sign from the drop-down menu.arrow_forwardChemistry complete for a rate. answer both questions for a rate 1. write out the mechanism for the reaction between ethyne and NaNH2. Label the acid snd the base predicting which way the reaction is favored. 2. do the same for C6H5OH and CH3CH2ONaarrow_forwardThe mass of nitration product is 0.50 grams, and melting range of the nitration product is 99 -101 degrees C. Use this information and the reported melting ranges to indicate the specific isomer product created in the experiment, and what that says about which substituent (ethoxy or N-acetyl) is the stronger ortho-directing group.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning