Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. 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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Try: Draw possible resonance contributing structures for the following organic species:
CH3CH2NO2
[CH2CHCH2] [CH2CHCHO]
[CH2CHCH2]
[CH2CHNH2]
Complete the following synthesis.
(d). H+
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Can the target compound be efficiently synthesized in good yield from the substituted benzene of the starting material?
If yes, draw the synthesis. Include all steps and all reactants.
Chapter 7 Solutions
Organic Chemistry
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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- IX) By writing the appropriate electron configurations and orbital box diagrams briefly EXPLAIN in your own words each one of the following questions: a) The bond length of the Br2 molecule is 2.28 Å, while the bond length of the compound KBr is 3.34 Å. The radius of K✶ is 1.52 Å. Determine the atomic radius in Å of the bromine atom and of the bromide ion. Br = Br b) Explain why there is a large difference in the atomic sizes or radius of the two (Br and Br). Tarrow_forwardWhen 15.00 mL of 3.00 M NaOH was mixed in a calorimeter with 12.80 mL of 3.00 M HCl, both initially at room temperature (22.00 C), the temperature increased to 29.30 C. The resultant salt solution had a mass of 27.80 g and a specific heat capacity of 3.74 J/Kg. What is heat capacity of the calorimeter (in J/C)? Note: The molar enthalpy of neutralization per mole of HCl is -55.84 kJ/mol.arrow_forwardWhen 15.00 mL of 3.00 M NaOH was mixed in a calorimeter with 12.80 mL of 3.00 M HCl, both initially at room temperature (22.00 C), the temperature increased to 29.30 C. The resultant salt solution had a mass of 27.80 g and a specific heat capacity of 3.74 J/Kg. What is heat capacity of the calorimeter (in J/C)? Note: The molar enthalpy of neutralization per mole of HCl is -55.84 kJ/mol. Which experimental number must be initialled by the Lab TA for the first run of Part 1 of the experiment? a) the heat capacity of the calorimeter b) Mass of sample c) Ti d) The molarity of the HCl e) Tfarrow_forward
- Predict products for the Following organic rxn/s by writing the structurels of the correct products. Write above the line provided" your answer D2 ①CH3(CH2) 5 CH3 + D₂ (adequate)" + 2 mited) 19 Spark Spark por every item. 4 CH 3 11 3 CH 3 (CH2) 4 C-H + CH3OH CH2 CH3 + CH3 CH2OH 0 CH3 fou + KMnDy→ C43 + 2 KMn Dy→→ C-OH ") 0 C-OH 1110 (4.) 9+3 =C CH3 + HNO 3 0 + Heat> + CH3 C-OH + Heat CH2CH3 - 3 2 + D Heat H 3 CH 3 CH₂ CH₂ C = CH + 2 H₂ → 2 2arrow_forwardWhen 15.00 mL of 3.00 M NaOH was mixed in a calorimeter with 12.80 mL of 3.00 M HCl, both initially at room temperature (22.00 C), the temperature increased to 29.30 C. The resultant salt solution had a mass of 27.80 g and a specific heat capacity of 3.74 J/Kg. What is heat capacity of the calorimeter (in J/C)? Note: The molar enthalpy of neutralization per mole of HCl is -55.84 kJ/mol.arrow_forwardQ6: Using acetic acid as the acid, write the balanced chemical equation for the protonation of the two bases shown (on the -NH2). Include curved arrows to show the mechanism. O₂N- O₂N. -NH2 -NH2 a) Which of the two Bronsted bases above is the stronger base? Why? b) Identify the conjugate acids and conjugate bases for the reactants. c) Identify the Lewis acids and bases in the reactions.arrow_forward
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