(b) The activating and deactivating groups could affect the position(s) of the next incoming group(s) to the benzene ring. Based on the structure below, analyze and explain the group(s) on the benzene ring is activating or deactivating group. Then, identify the product(s) formed from the following reactions. NH, „CCI, CH,CH,COCI AICI, (i) NH, HNO, H,SO, (ii) H Br AICI3 (iii)

(b) The activating and deactivating groups could affect the position(s) of the next incoming group(s) to the benzene ring. Based on the structure below, analyze and explain the group(s) on the benzene ring is activating or deactivating group. Then, identify the product(s) formed from the following reactions. NH, „CCI, CH,CH,COCI AICI, (i) NH, HNO, H,SO, (ii) H Br AICI3 (iii)

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 28VC

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Q6. Enolates and their surrogates. (a) Rank the acidity of the following compounds from LEAST (left) to MOST (right) by entering the corresponding numbers in the boxes provided. 1 4 2 NaNH, CO₂Me 5 3 CHO (b) Complete the following reaction products by adding the correct bonds, atoms and charges, as necessary.
b) Listed below are several hypothetical nucleophilic substitution reactions. None is synthetically useful because the product indicated is not formed at an appreciable rate. In each case provide an explanation for the failure of the reaction to take place as indicated. OMe HO + OMe + OH HO + CH; OH
Determine whether each of the following syntheses requires a reaction that alters the carbon skeleton. (a) (b) OH (c) (d) OCH,CH3 CH3 (e) OH (f) H,CO он H;CO. (g) H3CO, (h) H3CO. NO2 NO2
(b) The activating and deactivating groups could affect the position(s) of the next incoming group(s) to the benzene ring. Based on the structure below, analyze and explain the group(s) on the benzene ring is activating or deactivating group. Then, identify the product(s) formed from the following reactions. H H;C-C-c CH, Br AIC13 NH, so, H,SO4 (ii) NH, Hfos CH;C1 AICI, (iii)
Br Brz CH3 CH3 H3C CH2CI2 H3C Br Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl). In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br: :Br: .CH3 H3C H3C CH3 Br:
(b) Consider the reaction of 1-bromobutane with a large excess of ammonia (NH3). Draw the reactants, the transition state, andthe products. Note that the initial product is the salt of an amine (RNH3+ Br - ), which is deprotonated by the excess ammonia to give the amine.
Illustrate 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.
Which of the following reactions will synthesize phenol from benzene? 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) warm H2SO4 and H2O 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) CuCN; 5) dilute acid and heat 1) Acetyl chloride & AlCl3; 2) bleach 1) Ph-N2+ + KI; 2) BrMgCH=CH2 in ether, followed by H3O+; 3) warm, conc'd KMnO4 1) Cl-CH(CH3)-CH2CH2CH3 + FeBr3; 2) hot, conc'd KMnO4
The nitro groups on the benzene ring in the reactant serve two purposes.One is to let you know what atoms in the reactant correspond to what atomsin the product. But what role do the nitro groups play electronically – whywould the reaction be much slower if these nitro groups weren’t attached tothose benzene carbons? Draw any relevant structures to support youranswer.
Step 4: In an acid-catalyzed epoxide ring opening, the epoxide is first protonated and can then be attacked by weak nucleophiles. H HO: :Nuc Nuc Weak nucleophiles such as water and alcohols can react with the protonated epoxide. One of the main differences between base-catalyzed and acid-catalyzed epoxide ring openings is the regiochemical product expected. In an acid-catalyzed reaction, if one of the epoxide carbons is tertiary and the other primary, the nucleophile will attack at the more substituted carbon. If the epoxide is monosubstituted, the nucleophile will attack preferentially at the primary carbon vs. the secondary carbon. Which reaction will not give the indicated product? N 1. CH,CH,O 2. H₂O OH CH₂CH₂OH, H* N CH₂CH₂OH, H 1 CHICH,O 2. H₂O HO HO H- H
2. Draw the structures of the products that would result from the following reactions. Ph Ph (a) (c) Ph Ph co is also produced. Ph Ph. (b) O+ Ph-C C-Ph (d) Ph 10 Ph co is also produced. Benzyne adds to the 9, 10 position on anthracene.
Possible alternative brominations include: Veratrole (1,2-dimethoxybenzene) to 1,2-dibromo-4,5-dimethoxybenzene; 4-Methylacetanilide to 2-bromo-4-methylacetanilide; 2-Methylacetanilide (made in experiment S.1) to 4-bromo-2-methylacetanilide; Vanillin to 5-bromovanillin; Acetanilide to 4-bromoacetanilide; a. b. C. d. e. EXPERIMENT S4: BROMINATION OF AROMATIC COMPOUNDS Certain other acetanilides made in experiment S.1 may also be used as precursors in this experiment. Estimated time: 1 afternoon Associated learning goals: Section 6, LG 6.6; Section 7, LG 7.2 and 7.4 Pre-lab report: complete the standard report form, and answer the following questions. In this experiment, molecular bromine (Br2) is generated from the redox reaction of potassium bromate with hydrobromic acid. Write a balanced equation for this process. Briefly outline the mechanism by which Br2 brominates your aromatic compound. Why do the bromine atoms end up at the positions indicated rather than anywhere else in the…