Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 7, Problem 7.70P
Diphenhydramine, the antihistamine in Benadryl, can be prepared by the following two-step sequence. What is the structure of diphenhydramine?
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Fluorination of a benzene ring can be accomplished with Selectfluor, a reagent that contains a fluorine bonded to a positively charged nitrogen atom. Fluorination is a useful reaction because several common drugs, such as the cholesterol-lowering drug atorvastatin, contain a fluorine bonded to an aromatic ring. Assuming that fluorination is analogous to other examples of electrophilic aromatic substitution, draw a stepwise mechanism for the following reaction.
Fluorination of a benzene ring can be accomplished with Selectfluor, a reagent that contains a fluorine bonded to a positively charged nitrogen atom. Fluorination is a useful reaction because several common drugs, such as the cholesterol-lowering drug atorvastatin, contain a fluorine bonded to an aromatic ring. Assuming that fluorination is analogous to other examples of electrophilic aromatic substitution, draw a stepwise mechanism for the following reaction.
In the mid-1930s a substance was isolated from a fungus that is a parasite of ryes and other grasses. This alkaloid, lysergic acid, has
been of great interest to chemists because of its strange, dramatic action on the human mind. Many derivatives of lysergic acid are
known, some with medicinal applications. Perhaps the best known derivative of lysergic acid is the potent hallucinogen lysergic acid
diethylamide (LSD):
మగవా జి
N-H
LSD
(CH25N;O)
Like other alkaloids, LSD is a weak base, with Kp = 7.6 × 107. What is the pH of a 0.94 M solution of LSD?
pH =
Chapter 7 Solutions
Organic Chemistry-Package(Custom)
Ch. 7 - Classify each alkyl halide as 1 , 2, or 3.Ch. 7 - Problem 7.1 Telfairine, a naturally occurring...Ch. 7 - Draw the structure of an alkyl bromide with...Ch. 7 - Give the IUPAC name for each compound. a. b. c. d.Ch. 7 - Prob. 7.5PCh. 7 - An sp3 hybridized CCl bond is more polar than an...Ch. 7 - Prob. 7.7PCh. 7 - Problem 7.6 Identify the nucleophile and leaving...Ch. 7 - Prob. 7.9PCh. 7 - Prob. 7.10P
Ch. 7 - Prob. 7.11PCh. 7 - Prob. 7.12PCh. 7 - Does the equilibrium favor the reactants or...Ch. 7 - Prob. 7.14PCh. 7 - Prob. 7.15PCh. 7 - Classify each solvent as protic or aprotic. a. b....Ch. 7 - Prob. 7.17PCh. 7 - Prob. 7.18PCh. 7 - Prob. 7.19PCh. 7 - Prob. 7.20PCh. 7 - Prob. 7.21PCh. 7 - Draw an energy diagram for the reaction in Problem...Ch. 7 - Draw the product of each SN2 reaction and indicate...Ch. 7 - Prob. 7.24PCh. 7 - Prob. 7.25PCh. 7 - What happens to the rate of an SN1 reaction under...Ch. 7 - Draw the products of each SN1 reaction and...Ch. 7 - Classify each carbocation as 1,2, or 3. a. b. c....Ch. 7 - Prob. 7.29PCh. 7 - Prob. 7.30PCh. 7 - Which alkyl halide in each pair reacts faster in...Ch. 7 - Prob. 7.32PCh. 7 - Problem 7.30 For each alkyl halide and...Ch. 7 - Prob. 7.34PCh. 7 - Prob. 7.35PCh. 7 - Prob. 7.36PCh. 7 - Prob. 7.37PCh. 7 - Prob. 7.38PCh. 7 - Prob. 7.39PCh. 7 - Prob. 7.40PCh. 7 - Prob. 7.41PCh. 7 - Give the IUPAC name for each compound, including...Ch. 7 - Draw the products formed when each alkyl halide is...Ch. 7 - Give the IUPAC name for each compound. a. c....Ch. 7 - Prob. 7.45PCh. 7 - Classify each alkyl halide in Problem 7.44 as 1 ,...Ch. 7 - Draw the eight constitutional isomers having the...Ch. 7 - Prob. 7.48PCh. 7 - Draw the substitution product that results when...Ch. 7 - Draw the products of each nucleophilic...Ch. 7 - Prob. 7.51PCh. 7 - Rank the species in each group in order of...Ch. 7 - Which of the following nucleophilic substitution...Ch. 7 - Prob. 7.54PCh. 7 - Prob. 7.55PCh. 7 - Prob. 7.56PCh. 7 - 7.53 Consider the following reaction.
Draw a...Ch. 7 - Prob. 7.58PCh. 7 - Prob. 7.59PCh. 7 - Draw the products of each SN2 reaction and...Ch. 7 - Prob. 7.61PCh. 7 - Prob. 7.62PCh. 7 - Prob. 7.63PCh. 7 - Consider the following SN1 reaction. a.Draw a...Ch. 7 - Prob. 7.65PCh. 7 - Prob. 7.66PCh. 7 - Draw the products of each SN1 reaction and...Ch. 7 - Prob. 7.68PCh. 7 - Prob. 7.69PCh. 7 - Diphenhydramine, the antihistamine in Benadryl,...Ch. 7 - Draw a stepwise, detailed mechanism for the...Ch. 7 - When a single compound contains both a nucleophile...Ch. 7 - Prob. 7.73PCh. 7 - Prob. 7.74PCh. 7 - Draw a stepwise, detailed mechanism f or the...Ch. 7 - Prob. 7.76PCh. 7 - Fill in the appropriate reagent or starting...Ch. 7 - Devise a synthesis of each compound from an alkyl...Ch. 7 - Prob. 7.79PCh. 7 - Suppose you have compounds A-D at y our disposal....Ch. 7 - Prob. 7.81PCh. 7 - Prob. 7.82PCh. 7 - Prob. 7.83PCh. 7 - Prob. 7.84PCh. 7 - 7.80 As we will learn in Chapter 9, an epoxide is...Ch. 7 - Prob. 7.86PCh. 7 - In some nucleophilic substitutions under SN1...
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- The compound eutypine is an antibacterial agent isolated from the fungus Eutypa lata. This fungus results in a disease common to vineyards called eutyposis. Give a sequence of reactions that will take the following reactant and give eutypine when the other reactants used in the sequence are acetylene and acetone.arrow_forward(b) Draw a stepwise mechanism for the following transformation from A to B. This reaction is one of the key steps in a synthesis of lysergic acid diethyl amide (aka LSD). CI A CH ₂ AIC13 B CH₂ several steps away from lysergic acid diethyl amide (LSD)arrow_forwardKindly answer this questionarrow_forward
- Acetanilide is less reactive than aniline toward eletrophilic substitution. Explain.arrow_forwardBoth pyridine and pyrrole are nitrogen containing aromaticheterocyclic compounds. When treated with HCI, only pyridine forms a hydrochloride salt, whereas pyrrole is unreactive Which of the following is not a valid explanation for this observed reactivity? pyridine ругrole O The lone pair on pyridine is not part of the aromatic system. O The lone pair on pyridine can be protonated without disrupting the aromatic stability. O The lone pair on pyrrole is sp hybridized and is less prone to protonation. O Protonation of pyrrole leads to a nonaromatic cation, which is less stable O The lone pair on pyrrole is involved in making the compound aromatic and thus is less susceptible to protonation.arrow_forwardLook at the imide, the nitrogen analog of an anhydride below: a) For a neutral imide, will the carbonyl carbon be more (easier to attack) orless (harder to attack) electrophilic than the C of a neutral anhydride? Talk about electronegativties of Nitrogen (imide) vs Oxygen (anyhydride) b) If the imide is hydrolyzed under acidic conditions, which atom, one of theoxygens or the nitrogen, will be protonated? Explain your answer. Talk about pka and keq.arrow_forward
- Both pyridine and pyrrole are nitrogen containing aromatic heterocyclic compounds. When treated with HCl, only pyridine forms the hydrochloride salt, where as pyrrole is unreactive. What is the best explanation for this observed reactivity.arrow_forwardMinoxidil is a molecule that causes hair growth in some people. It was originally synthesized as a vasodilator for the treatment of hypertension (high blood pressure). Most of the patients taking the drug for hypertension were seen to grow body hair. Due to other side effects, its oral use was stopped, but it became popular as a topical cream to promote hair growth. The first key reaction in one synthesis of minoxidil follows. Draw the product of this reaction.arrow_forwardThe following molecule undergoes an intramolecular reaction in the presence of pyrrolidinium acetate, the protonated form of pyrrolidine. Draw the product of this reaction, assuming that a dehydration reaction takes place.arrow_forward
- B) Rank the following compounds toward increasing acidity, why? 2) 1,3-benzoqounoin 2)cyclohexanoic acid 3)cyclohexanal 4) cyclohexanolarrow_forwardCoumarin, a naturally occurring compound isolated from lavender, sweet clover, and tonka bean, is made in the laboratory from o-hydroxybenzaldehyde by the reaction depicted below. Draw a stepwise mechanism for this reaction. Coumarin derivatives are useful synthetic anticoagulants.arrow_forwardWhen acetophenone, hydroxelamine hydrochloride, and sodium hydroxide are reacted to synthesize acetophenone oxime, why is it necessary to add hydrochloric acid after the reaction to make it acidic?arrow_forward
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