Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Question
Chapter 23, Problem 23.54P
Interpretation Introduction
(a)
Interpretation: The intermediates
Concept introduction: Ibuprofen is a synthetic compound which is widely used as a drug and as an analgesic and anti-inflammatory. It is synthesized from
Interpretation Introduction
(b)
Interpretation: The product formed by the direct alkylation of compound
Concept introduction: Ibuprofen is a synthetic compound which is widely used as a drug and as an analgesic and anti-inflammatory. It is synthesized from
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Which of the following reactions will not produce N-methylbutanamine?
O a. Reduction of N-methylbutanamide with LIAIH4.
O b. The reaction of butanoyl chloride with methanamine.
OC. The reaction of methanamine with 1-butyl bromide and subsequent reaction with a strong base.
O d. The reaction of 1-butanamine with methyl bromide and subsequent reaction with a strong base.
Identify the reaction type.
a. hydrolysis (in acid)
b. hydration
c. dehydration
d. acid base
e. esterification
f. amide synthesis
g. hydrolysis (in base)
What reagents would you use to convert methyl propanoate to the following compounds? a. isopropyl propanoate b. sodium propanoate c. N-ethylpropanamide d. propanoic acid
Chapter 23 Solutions
Organic Chemistry-Package(Custom)
Ch. 23 - Problem 23.1 Draw the enol or keto tautomer(s) of...Ch. 23 - Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.3PCh. 23 - Prob. 23.4PCh. 23 - Which CH bonds in the following molecules are...Ch. 23 - Prob. 23.6PCh. 23 - Prob. 23.7PCh. 23 - When ethyl acetoacetate (CH3COCH2CO2CH2CH3) is...Ch. 23 - Prob. 23.9PCh. 23 - Prob. 23.10P
Ch. 23 - Prob. 23.11PCh. 23 - Problem 23.11 Draw the products of each...Ch. 23 - Problem 23.12 Draw the products of each reaction....Ch. 23 - Prob. 23.14PCh. 23 - Prob. 23.15PCh. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Prob. 23.18PCh. 23 - Problem 23.18 How can pentan-2-one be converted...Ch. 23 - Problem 23.19 Identify A, B, and C, intermediates...Ch. 23 - Prob. 23.21PCh. 23 - Problem 23.21 Draw the products of each...Ch. 23 - Prob. 23.23PCh. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Prob. 23.25PCh. 23 - Prob. 23.26PCh. 23 - Prob. 23.27PCh. 23 - Prob. 23.28PCh. 23 - Prob. 23.29PCh. 23 - 23.29 Draw enol tautomer(s) for each compound....Ch. 23 - 22.30 The cis ketone A is isomerized to a trans...Ch. 23 - Draw enol tautomers for each compound. a. b. c.Ch. 23 - Prob. 23.33PCh. 23 - What hydrogen atoms in each compound have a pKa25?...Ch. 23 - Rank the labeled protons in each compound in order...Ch. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - Prob. 23.38PCh. 23 - Prob. 23.39PCh. 23 - 23.38 Acyclovir is an effective antiviral agent...Ch. 23 - Prob. 23.41PCh. 23 - 23.39 Explain why forms two different alkylation...Ch. 23 - 23.41 Acid-catalyzed bromination of pentanone ...Ch. 23 - Draw a stepwise mechanism for each reaction. a. b.Ch. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Use the malonic ester synthesis to prepare each...Ch. 23 - 23.45 Devise a synthesis of valproic acid , a...Ch. 23 - Synthesize each compound from diethyl malonate....Ch. 23 - Prob. 23.49PCh. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Synthesize each compound from ethyl acetoacetate....Ch. 23 - Draw the organic products formed in each reaction....Ch. 23 - 23.51 Draw the products formed (including...Ch. 23 - Prob. 23.54PCh. 23 - 23.54 Clopidogrel is the generic name for Plavix,...Ch. 23 - 23.55 What reaction conditions—base, solvent, and...Ch. 23 - Explain why each of the following reactions will...Ch. 23 - Prob. 23.58PCh. 23 - 23.57 Draw a stepwise mechanism showing how two...Ch. 23 - 23.58 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.61PCh. 23 - 23.60 Draw stepwise mechanisms illustrating how...Ch. 23 - Prob. 23.63PCh. 23 - Prob. 23.64PCh. 23 - Convert acetophenone (C6H5COCH3) into each of the...Ch. 23 - Prob. 23.66PCh. 23 - Prob. 23.67PCh. 23 - Prob. 23.68PCh. 23 - Synthesize each product from ethyl acetoacetate...Ch. 23 - Prob. 23.70PCh. 23 - Prob. 23.71PCh. 23 - 23.68 Capsaicin, the spicy component of hot...Ch. 23 - 23.69 Treatment of W with , followed by , affords...Ch. 23 - Prob. 23.74PCh. 23 - Prob. 23.75PCh. 23 - Prob. 23.76PCh. 23 - Prob. 23.77PCh. 23 - Prob. 23.78P
Knowledge Booster
Similar questions
- Synthesis of p-Bromoaniline Why is a sodium acetate solution added in part 1? a) The sodium ion directs the position of the acetyl group. b) To protonate the intermediate and make it less soluble. c) The acetate catalyzes the formation of the amide bond. d) To deprotonate the intermediate and make it less solublearrow_forwardare involved in the regulation of glucose metabolism and in control tissue swelling by the control of inflammation, while regulating cellular salt balance between Na+ and K+. a.glucocorticoids, mineralocorticoids b. mineralocorticoids, glucocorticoids c. androgen, estrogen d. estrogen, androgen Which of the following represents an aldonic acid? OH OH но, но OH но —н но Но HO HO H но но H H- -OH -OH H OH H FOH H- -OH- OH HO но HO. OH II III IV V Refer to the structures. Which of the following compounds will react with acetyl chloride to give an amide and ester, respectively? NH2 ÇOOH CH3 он CHO II II IV V The six groups of enzymes are the following: I. Oxidoreductases II. Transferases III. Hydrolases IV. Isomerases V. Lyases VI. Ligases Fill in the blanks: catalyze hydrolysis while catalyze bond formation.arrow_forwardPart A: Draw the product of the reaction of propylamine with water Part B: Draw the product of the neutralization of propylamine with HBr Part C: Draw the product of the reaction of N-methylaniline with waterarrow_forward
- Treatment of α,β-unsaturated carbonyl compound X with base forms the diastereomer Y. Write a stepwise mechanism for this reaction. Explain why one stereogenic center changes configuration but the other does not.arrow_forwardWhich one-carbon group is carried by N5-methyl-tetrahydrofolate? A. Carbon dioxide B. aldehyde C. methyl D. hydroxymethylarrow_forwardWhat product is obtained from the reaction of N,N-dimethylaniline with nitrous acid? A. benzenediazonium chloride B. Azodye C. p-NO-C,H4-N(CH3)2 D. o-NO-C,H4-N(CH3)2arrow_forward
- 15. What is the balanced chemical equation for the aromatic bromination of Acetanilide using green reagents Sodium Bromide, Bleach, Acetic Acid, and Ethanol?arrow_forwardTyramine is an alkaloid found in mistletoe and ripe cheese. Dopamine is a neurotransmitter involved in the regulation of the central nervous system. a. How can tyramine be prepared from β-phenylethylamine?b. How can dopamine be prepared from tyramine?c. Give two ways to prepare β-phenylethylamine from β-phenylethyl chloride.d. How can β-phenylethylamine be prepared from benzyl chloride?e. How can β-phenylethylamine be prepared from benzaldehyde?arrow_forwardp-toluic acid is prepared from 3.42 grams of p-Bromotoluene. When p-Bromotoluene was mixed with dry ether, the mixture was warmed until the ether begins to boil (34.6 °C). When the reaction is almost complete, dry ice (3-4 mL in a beaker) was prepared and the mixture was poured into it. After some time, 5 mL of 6 N HCl was added. The solvent used for the recrystallization is 100 mL of 30% ethanol. The reaction equation is given on the figure. What is the actual yield? What is the theoretical yield? How many moles of p-toluic acid was produced?arrow_forward
- a-phellandrene and ß-phellandrene are two isomeric diene-containing terpene compounds isolated from eucalyptus plants that are used in fragrances due to their minty and citrusy odors. Use these two compounds to answer the following two questions: a. The addition of 1 equivalent of bromine at room temperature to the phellandrenes will give three possible di-brominated products. Select either a- or ß-phellandrene for this question and draw it in the left box - you can answer this question with either isomer. Draw all three products in the colored boxes depicted - you do not need to depict newly formed stereocenters or show mechanisms. OR a-phellandrene B-phellandrene product 1 select either a- or B-phellandrene product 2 Br₂ room temperature 3 possible products (see below) product 3arrow_forward5. Butylated hydroxy toluene (BHT) is an anti-oxidant added to many food products (e.g. breakfast cereals) to increase their shelf-life. BHT is synthesized from p-cresol by reaction with 2-methylpropene in the presence of phosphoric acid. a) What is the structure of BHT ? b) Account for the regioselectivity of tert-butyl group substitution in the synthesis of BHT. c) Propose a mechanism to explain the formation of the electrophile in the synthesis of BHT.arrow_forwardWhy is methyl salicylate so easily absorbed through the skin?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning