1. (a) Formulate four(4) different ways to synthesize 3-methylhexane from any readily available starting material. For each of these, show the reagent(s) required for each transformation, including all intermediates. (b) H.C. Brown used ester (2A) to test a new reducing agent which did indeed form alcohol (2B). How might he have made the ester (2A) from benzene. 2A C2Me NaBH4 AICI 3 CI 2B CH₂OH (c) Suggest synthesis for the target molecules (3A) and (3B) needed as intermediates. TM (3A) in the synthesis of brominated hydroxybenzoic acids and TM (3B) in the synthesis of model compounds for studying biological mechanisms of ester hydrolysis. OH CO₂ CHO O₂N Br

1. (a) Formulate four(4) different ways to synthesize 3-methylhexane from any readily available starting material. For each of these, show the reagent(s) required for each transformation, including all intermediates. (b) H.C. Brown used ester (2A) to test a new reducing agent which did indeed form alcohol (2B). How might he have made the ester (2A) from benzene. 2A C2Me NaBH4 AICI 3 CI 2B CH₂OH (c) Suggest synthesis for the target molecules (3A) and (3B) needed as intermediates. TM (3A) in the synthesis of brominated hydroxybenzoic acids and TM (3B) in the synthesis of model compounds for studying biological mechanisms of ester hydrolysis. OH CO₂ CHO O₂N Br

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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(a) Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Give two reasons.(b) How will you bring about the following converstions?(i) Propanone to propane (ii) Benzoyl chloride to benzaldehyde(iii) Ethanal to but-2-enal
The hydrocarbon fluorene was treated with potassium t-butoxide in an acid-base reaction, giving the fluorenide anion and t-butyl alcohol. (a) Which way does the equilibrium lie, and by how much? b) What is the proportion of the fluorenide anion to fluorene? (c) Why is fluorene so highly acidic, considering the pKa of an average alkane is above 50?
(a) Give the products of the phosphoric acid-catalyzed dehydration of 2-methylcyclohex-3- enol. Label the three products with major, minor, and trace amounts. OH H3PO4, heat (b) Describe the rule that is applied in the acid-catalyzed dehydration of 2-methylcyclohex-3- enol. Explain your answer based on the products formed.
(b) Compound AA has a molecular formula of CsH&O and gives a positive result using Tollen's reagent. The reaction of compound AA with hot acidified potassium permanganate, KMNO4 gives compound BB. The catalytic hydrogenation of compound AA with nickel, Ni produced compound Cc. The reaction of compound BB with ethanamine, CH:CH2NH2 produces compound DD. Sebatian AA mempunyai formula molekul C3He0 dan memberikan keputusan yang positif menggunakan reagen Tollen. Tindak balas sebatian AA dengan larutan panas kalium permanganat, KMNO4 berasid menghasilkan sebatian BB. Penghidrogenan bermangkin bagi sebatian AA dengan nikel, Ni menghasilkan sebatian CC. Tindak balas sebatian BB dengan etanamina, CH3;CH2NH2 menghasilkan sebatian DD. (1) Draw the structural formula of compounds AA, BB, CC and DD. Lukiskan formula struktur bagi sebatian AA, BB, CC dan DD. (i) Name the type of chemical reaction for the formation of compound CC. Namakan jenis tindak balas kimia bagi penghasilan sebatian Cc.
(a) Account for the following :(i) Propanal is more reactive than propanone towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give characteristic reactions of carbonyl group.(b) Give simple chemical test to distinguish between the following pairs of compounds:(i) Acetophenone and benzaldehyde(ii) Benzoic acid and ethylbenzoate.
(b) Your task is to prepare styrene by one of the following reactions. Which reaction would you choose to give the better yield of styrene? Explain your answer. Br KOH EtOH, A (ii) KOH EtOH, A
(a) How will you carry out the following conversions?(i) Acetylene to Acetic acid (ii) Toluene to m-nitrobenzoic acid(iii) Ethanol to Acetone(b) Give reasons :(i) Chloroacetic acid is stronger than acetic acid.(ii) pH of reaction should be carefully controlled while preparing ammonia derivatives of carbonyl compounds.
(a) Illustrate the following name reactions :(i) Reimer-Tiemann Reaction (ii) Williamson Synthesis.(b) Give a chemical test to distinguish between 2-propanol and 2-methyl-2-propanol.
Apply retrosynthetic analysis to guide the preparation of each of the following compounds from the indicated starting material, then write out the synthesis showing the necessary reagents. (a) 1-Propanol from 2-propanol (b) 1,2-Dibromopropane from 2-bromopropane (c) 1-Bromo-2-propanol from 2-propanol (d) 1-Bromo-2-methyl-2-propanol from tert-butyl bromide (e) 1,2-Epoxypropane from 2-propanol (f) tert-Butyl alcohol from isobutyl alcohol (g) tert-Butyl iodide from isobutyl iodide (h) trans-2-Chlorocyclohexanol from cyclohexyl chloride
2. (a) Starting with Propanol (CH₂CH₂CH₂OH), show how would you synthesize the following substances? Use equations only, showing structures of reactants, reagents and all intermediate products. (i) 3-Hexanol {CH,CH₂CH₂(OH)CHCH₂CH3} (ii) Propanoic acid (CH,CH,COOH) (iii) 2-Pentene (CH3CH₂CH=CHCH3) (iv) Ethyl propyl ether (CH-CH₂CH₂OCH₂CH3) CH₂CH₂ CH₂CH₂ CH₂ ol when Synthesizing: alcohol RICH
(a) How will you convert:(i) Benzene to acetophenone (ii) Propanone to 2-Methylpropan-2-ol(b) Give reasons :(i) Electrophilic substitution in benzoic acid takes place at meta position.(ii) Carboxylic acids are higher boiling liquids than aldehydes, ketones and alcohols of comparable molecular masses.(iii) Propanal is more reactive than propanone in nucleophilic addition reactions.