6. Some reactions of 2-iodopropane are shown below: reaction 1 CH;CHCH; reaction 3 (CH3),CHOCH; CH;CH=CH, reaction 2 (CH3)½CHNH, i) For each of the reactions shown, name the reagent used and state the condition of reaction. ii) State the type of mechanism of hydrolysis reaction in 2-iodopropane. iii) Write the mechanism involve in the reaction

6. Some reactions of 2-iodopropane are shown below: reaction 1 CH;CHCH; reaction 3 (CH3),CHOCH; CH;CH=CH, reaction 2 (CH3)½CHNH, i) For each of the reactions shown, name the reagent used and state the condition of reaction. ii) State the type of mechanism of hydrolysis reaction in 2-iodopropane. iii) Write the mechanism involve in the reaction

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter6: Reactions Of Alkenes

Section: Chapter Questions

Problem 6.31P: When 2-pentene is treated with Cl2 in methanol, three products are formed. Account for the formation...

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3. (a) Complete the following reactions and write the name of products (i) 1. HNO3, H2SO4 AICI3 2. Zn(Hg), HCI (ii) 1. HBr 2. NaOCH3 3 (iii) ??? H2N-NHCON2 Aq. KOH C6H5CH2OH → BENZALDEHYDE A В (b)What happens when (write reactions involved) (iv) Phenol reacts with sodium metal and resulting product reacts with 2-chloropropane (v) Ethanal reacts with HBr and the resulting product is dehydrated (vi) Ethoxyethane is hydrolyzed to produce a compound A which dehydration produces B. B on ozonolysis produces C. Write the reaction and identify A, B, and C.
Which of the following reactions will synthesize phenol from benzene? 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) warm H2SO4 and H2O 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) CuCN; 5) dilute acid and heat 1) Acetyl chloride & AlCl3; 2) bleach 1) Ph-N2+ + KI; 2) BrMgCH=CH2 in ether, followed by H3O+; 3) warm, conc'd KMnO4 1) Cl-CH(CH3)-CH2CH2CH3 + FeBr3; 2) hot, conc'd KMnO4
8. a) b) Provide structure(s) for the starting material(s), reagent(s) or the major organic product(s) of each of the following reactions. OEt COOH CH3 CH; 0 OH 1. LiAlH4, ether 2. HO OH ند (CH3COO NaOH, H₂O 5 CH 3 Cl
Predict the products of the following acid-base reactions. If the equilibrium would not result in the formation of appreciable amounts of products, you should so indicate. In each case label the stronger acid, the stronger base, the weaker acid, and the weaker base: (a) CH3CH=CH2 + NANH2 (d) CH3C=C: + CH;CH2OH → (e) CH3C=C:- + NH¾CI – | (b) CH;C=CH + NaNH2 (c) CH3CH2CH3 + NANH2 → | HAS
Write IUPAC name of the products obtained by addition reactions of HBr to hex – 1 –ene.(i) in the absence of peroxide, and(ii) in the presence of peroxide.
5. Consider the synthesis of 2-butanone from butyne: Hg2+ CH3CH,-C=C–H CH3CH, Ĉ -CH3 H3o* (i) Draw the structure of the compound D. (ii) Compound D isomerizes to form 2-butanone. What is this isomeric process called? (iii) Use the mechanism to show the conversion of compound D to 2-butanone.
Give reasons for the following: (i) p-nitrophenol is more acidic than p-methylphenol. (ii) Bond length of C—O bond in phenol is shorter than that in methanol. (iii) (CH3)3C—Br on reaction with sodium methoxide (Na+ _OCH3) gives alkene as the main product and not an ether.
An important step in one synthesis of carboxylic acids is the deprotonation of diethyl malonate and its alkyl-substituted derivative: Base CH;CH2O OCH,CH3 CH;CH,0 OCH2CH3 H2 Diethyl malonate Base CH;CH,0 °C `OCH,CH3 CH;CH,O OCH,CH3 R Alkyl substituted diethyl malonate NaOH can deprotonate diethyl malonate effectively, but NaOC(CH3)3 is typically used to deprotonate the alkyl-substituted derivative. Explain why.
(d) When butane, CH3CH2CH2CH3 and bromine gas, Br2 is exposed to sunlight, monobrominated product are produced. The reaction equation is given below: uv CH;CH,CH,CH3 + Br2 A + B (i) State the type of reaction. (ii) What is the function of the sunlight in the reaction? (iii) Draw the structure of monosubstituted products, A and B. Label the major product. (iv) Draw the propagation steps in the mechanism for the formation of the major product.
| Exercises 317 9.21 Identify the reactants from which the following molecules were prepared. If an acetal, identify the carbonyl compound and the alcohol; if an imine, identify the carbonyl compound and the amine; if an alcohol, identify the carbonyl compound and the Grignard reagent (red = 0, blue = N): (a) (b) (c)
) Write the reaction mechanism for the acid-catalyzed dehydration of a tertiary butyl alcohol. 5.) Predict the major products of the following reactions. H,C =CH, + HBr H,C ROOR CH,CH=CH, - HBr
4. Protonation of alcohol A and subsequent loss of water, produces the intermediate B. CH3 CH; CH, CH, — с — сH, CH, CH;CH, - C- CH, CH; | OH A B (a) (i) Name alcohol A. (11) What type of species is intermediate B? (iii) Draw the structures of the two alkenes which can be formed from species B by removal of a proton. Label as C the alkene which shows geometrical isomerism. (b) The intermediate B is readily attacked by nucleophiles such as water. What is the essential feature of a nucleophile? (c) State what final colour you would see if alcohol A were warmed with acidified potassium dichromate(VI). Explain your answer. Colour Explanation . (ii) Draw two structural isomers of alcohol A which form branched chain ketones when heated with acidified potassium dichromate(VI), but which could not form alkene C on dehydration.