Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 22.SE, Problem 24MP
In the Hell–Volhard–Zelinskii reaction, only a catalytic amount of PBr3 is necessary because of the equilibrium below. Review the mechanism for the reaction of a
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Show how the reagent for Step 6 can be prepared from salicylic acid (2-hydroxybenzoic acid). Salicylic acid, the starting material for the synthesis of aspirin and a number of other pharmaceuticals, is readily available by the Kolbe carboxylation of phenol
Identify the best reagents to complete the following reaction. Options are included.
H3C
OH
1. Br2, PBг3
2. H₂O
H3C
OH
Br
The a-bromination of carbonyl compounds by Br₂ in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can
be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the
acid bromide completes the reaction.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
Br
Br
зь
P-Br
Br
H₂C
H₂C
SH
Br
Br
Chapter 22 Solutions
Organic Chemistry
Ch. 22.1 - Prob. 1PCh. 22.1 - How many acidic hydrogens does each of the...Ch. 22.1 - Prob. 3PCh. 22.3 - Write the complete mechanism for the deuteration...Ch. 22.3 - Prob. 5PCh. 22.4 - If methanol rather than water is added at the end...Ch. 22.5 - Prob. 7PCh. 22.5 - Draw a resonance structure of the acetonitrile...Ch. 22.6 - If methanol rather than water is added at the end...Ch. 22.7 - Prob. 10P
Ch. 22.7 - Draw a resonance structure of the acetonitrile...Ch. 22.7 - Why do you suppose ketone halogenations in acidic...Ch. 22.7 - Prob. 13PCh. 22.7 - Prob. 14PCh. 22.7 - Prob. 15PCh. 22.7 - Prob. 16PCh. 22.SE - Prob. 17VCCh. 22.SE - Prob. 18VCCh. 22.SE - Prob. 19VCCh. 22.SE - Prob. 20MPCh. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Prob. 23MPCh. 22.SE - In the Hell–Volhard–Zelinskii reaction, only a...Ch. 22.SE - Prob. 25MPCh. 22.SE - Nonconjugated , -unsaturated ketones, such as...Ch. 22.SE - Prob. 27MPCh. 22.SE - Using curved arrows, propose a mechanism for the...Ch. 22.SE - Prob. 29MPCh. 22.SE - One of the later steps in glucose biosynthesis is...Ch. 22.SE - The Favorskii reaction involves treatment of an...Ch. 22.SE - Treatment of a cyclic ketone with diazomethane is...Ch. 22.SE - Prob. 33MPCh. 22.SE - Amino acids can be prepared by reaction of alkyl...Ch. 22.SE - Amino acids can also be prepared by a two-step...Ch. 22.SE - Heating carvone with aqueous sulfuric acid...Ch. 22.SE - Identify all the acidic hydrogens (pKa 25) in the...Ch. 22.SE - Rank the following compounds in order of...Ch. 22.SE - Prob. 39APCh. 22.SE - Base treatment of the following , -unsaturated...Ch. 22.SE - Prob. 41APCh. 22.SE - Prob. 42APCh. 22.SE - Prob. 43APCh. 22.SE - Which, if any, of the following compounds can be...Ch. 22.SE - Prob. 45APCh. 22.SE - Prob. 46APCh. 22.SE - Prob. 47APCh. 22.SE - How might you convert geraniol into either ethyl...Ch. 22.SE - Prob. 49APCh. 22.SE - One way to determine the number of acidic...Ch. 22.SE - Prob. 51APCh. 22.SE - Prob. 52APCh. 22.SE - Prob. 53APCh. 22.SE - Prob. 54APCh. 22.SE - Prob. 55APCh. 22.SE - Prob. 56APCh. 22.SE - All attempts to isolate primary and secondary...Ch. 22.SE - How would you synthesize the following compounds...Ch. 22.SE - Prob. 59APCh. 22.SE - Prob. 60APCh. 22.SE - Prob. 61APCh. 22.SE - Prob. 62APCh. 22.SE - As far back as the 16th century, South American...Ch. 22.SE - The key step in a reported laboratory synthesis of...Ch. 22.SE - Prob. 65AP
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- Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forwardDraw a structural formula for the major organic product of each reaction and specify the most likely mechanism by which each is formed. (g) CH3CH2ONa++CH2=CHCH2Clethanolarrow_forwardGive detailed Solution with explanation neededarrow_forward
- Please don't provide handwritten solutionarrow_forward1. Br₂, PBrg 2. H₂O H₂C OH H3C OH Br The a-bromination of carbonyl compounds by Br₂ in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br₂ reacts in an α- substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H3C :0: :0::Br: Br Br H3C CO-P H Br Brarrow_forwardThe following reaction involves two sequential Heck reactions. Draw structural formu- las for each organopalladium intermediate formed in the sequence and show how the final product is formed. Note from the molecular formula given under each structural formula that this conversion corresponds to a loss of H and I from the starting material. Acetonitrile, CH,CN, is the solvent. 1% mol Pd(OAc), 4% mol Ph,P CH,CN C4H171 C4H16arrow_forward
- Pleas explain how this process occurs. Identify SN1, SN2, E2, E1, nucleophiles and electrophiles.arrow_forwardComplete the following reaction sequences by drawing the major products or the reagents necessary to make them. Be sure to include stereochemistry when appropriate. dont provide handwritten solutionarrow_forwardDraw mechanisms for the acetylation of aniline, the bromination of acetanilide and the hydrolysis of 4-bromoacetanilide (REMEMBER: NBS generates bromine in solution) Reagents used: aniline, acetic acid, acetic anhydride to make acetanilide. Then acetanilide dissolved in acetic acid, NBS, aqHBr to make 4-bromoaxetanilinde. Then 4-bromoacetanilinde, EtOh, HCl and NaOH (to neutralise) to make 4-bromoaniline Please include drawings of the mechanisms as well as a written explanation as it helps me process exactly whats going on...arrow_forward
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