Concept explainers
Interpretation:
The synthesis of the given products using maleic or fumaric acid and any other needed compounds is to be outlined.
Concept introduction:
Diels Alder reaction is a type of cycloaddition reaction that takes place between a conjugated diene derivative and a dienophile derivative, resulting in the addition of these compounds and the generation of a ring.
Dienes are compounds containing two double bonds. Conjugated ones are those in which the double bonds are in conjugation with each other. Only those dienes that have
Dienophiles are compounds containing one double bond and have electron withdrawing groups, such as cyano and esters, attached to them. Stereochemistry of dienophile is retained during the Diels Alder reaction.
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Chapter 17 Solutions
Organic Chemistry
- (c) Arrange the following compounds in order of increasing acidity, and explain the reasons for your choice of order: phenol, cyclohexanol, 2-fluorocyclohexanol, 2-fluorophenol.arrow_forwardArrange the following compounds in the increasing order of their acid strength: p-cresol, p-nitrophenol, phenolarrow_forward(a) Arrange the following compounds in an increasing order of their indicated property :(i) Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid (acid strength)(ii) CH3CH2CH (Br) COOH, CH3CH (Br) CH2COOH,(CH3)2CHCOOH, CH3CH2CH2COOH (acid strength)(b) How would you bring about the following conversions :(i) Propanone to Propene (ii) Benzoic acid to Benzaldehyde(iii) Bromobenzene to 1-phenylethanolarrow_forward
- (a) Explain how NaBH, in CH;OH can reduce hemiacetal A to 1,4-butanediol (HOCH,CH,CH,CH,OH). (b) What product is formed when A is treated with Ph;P=CHCH,CH(CH),? (c) The drug isotretinoin is formed by reaction of X and Y. What is the structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it is dispensed under strict controls because it also causes birth defects. PPha NaOCH,CH3 HO- isotretinoin HO A Br X Yarrow_forwardIdentify (A) in the following reaction. 2H2 Pt (A) KMNO4 Warm conc. || С — С — о—н |CO,H + HO CO2H cis-cyclo hexane 1,2-dicarboxylic acid (a) (b) (c) (d)arrow_forwardGive reasons for the following :(i) Phenol is more acidic than methanol.(ii) The C—O—H bond angle in alcohols is slightly less than the tetrahedral angle (190°28′).(iii) (CH3)3C—O—CH3 on reaction with HI gives (CH3)3C—I and CH3—OH as the main products and not (CH3)3C—OH and CH3—I.arrow_forward
- 19.58 For each of the following questions, please provide a route that could reasonably be expected to convert the starting material into the product. In each case, more than one reaction is required, and reactions you have learned in previous chapters may be needed to solve the problem. -8 8 (b) Jos 1-3 (d) NH₂ OEt OEt OEt Eto OH LOH 5- OH H₂N OH "NH₂ Oarrow_forward(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) Ph Ph 836 Ph THF A 1 B H₂SO4 100 °C 3 OH Which of the two methods (A or B) is more likely give high yield of methylenecyclohexane 2? Briefly explain.arrow_forwardElectrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict the major products of the reactions of naphthalene with the following reagents.(a) isobutylene and HF (b) cyclohexanol and BF3 (c) fuming sulfuric acidarrow_forward
- Triethanolamine, (HOCH2CH2)3N, is a widely used biological buffer, with maximum buffering capacity at pH 7.8. Propose a synthesis of this compound from ethylene oxide and ammonia.arrow_forward(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) 1 Ph THF A Ph Ph B H₂SO4 100 °C 3 OH What is the name of the reaction that is followed by reaction Method A?arrow_forward6) If you are given a mixture consisting of following 3 compounds, explain how you would separate the components by solvent extraction method NH2 ÇOOH (A) Cyclopentylamine (B) 2,4-Cyclopentadiene-1-carboxylic acid (C) Benzenearrow_forward