(i) Suggest structures for the reagents and products in the boxes labelled A to Hin the reaction scheme below.02CD + E (+butane)A+ 2B"BuLi(-LICI)F (-butane)PhNMe2Ph =G+LiBr(-butane)BuH"BuMg-Br"Bu(ii) Products D and E are formed in competing reactions. Suggest an alternativereagent to "BuLi that may favour formation of product E. Briefly explain yourreasoning.

The reaction given involves various reagents and intermediates to produce different products. The…

Answered: (i) Suggest structures for the reagents…

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

Chapter5: Alkenes: Bonding, Nomenclature, And Properties

Section: Chapter Questions

Problem 5.31P

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(b) Predict the suitable solvent (H2O or CH3COCH3) to increase the reaction of bromopropane (CH3CH2CH2B1) with sodium hydroxide (NaOH). Two reactions are shown below: NaOH, 55 °C CH;CH,CH,Br CH;CH,CH,OH + NaBr H,O (i) NaOH, 55 °C CH;CH,CH,Br CH;CH,CH,OH NaBr H,C CH (ii)
A medicinal chemist at Orgalex Labs, a little known division of a big international pharmaceutical firm, has predicted the major product of the following reacti an early step in the synthesis of Compound R40 (rumored to be a cure for rhinitis, spontaneous combustion, and bad luck): or=0x0 HBr OH As Vice-President of Research, it's your job to decide whether the chemist has made a reasonable prediction. • If your answer is yes, these could be the major products of the reaction, draw the complete mechanism for the reaction below. • If your answer is no, check the box under the drawing area. Ö U OH Br H-Br Add/Remove step Click and drag to start drawing a structure.
(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.
5) The following question concerns redox methodology: Present answers in the form of structures, mechanisms, reagents or explanations for the arrows associated with the following reductions: give a structure Ph. a) i) LIAIH, / ether /-10°C C3H100 CO,Me ii) H20 A Present a mechanism give reagents Lindlar Comment on the chemo- and b) stereoselectivity. give reagents and conditions CO,Me CO,Me Birch Present a mechanism and hence c) explain the regioselectivity 100% 0%
(b) Reactivity with the S1 by the treatment with NaOH Br Br I t 2 (c) Solubility in hexane: Br H3C-Br
Identify the reagent used in the following transformation: OH P Q HO HO P = LIAIH, Q = KMNO, Q = MnO, / CH,Cl, Q = Ag,CO, on celite, PhH (A) (B) P= NABH, /MeOH %3D (C) P=CeCl,.7H,O (D) P= NABH, /CeCl,.7H,0 , / CeCly.7H,O Q = MnO, / CH,Cl,
(b) From the following molecules, A-D, a rotaxane can be formed. B NH i. ii. A HN H 'N C H D Cd(CIO4)2 NH₂ Draw the structure of the possible rotaxane that can be formed by molecules A-D. Give the order you would add the above molecules in order to synthesise a rotaxane. Justify your chosen order.
(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 8*8 Ph THF A 1 Santande B H₂SO4 100 °C 3 OH Using curly arrows, provide full mechanistic details accounting how methylenecyclohexane 2 was synthesised according to both Methods A and B.
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.
3. Provide the products, intermediates, and/or reagents for the following reactions: (a) CH3 (i) H2N CH3 pyridine Ph (b) он PBr3 PPh, кови (ii) (iii) (iv) then (c) Ph Br. (v) CH3 (d) HNO, (excess) (vi) CH3 H2SO4 (e) 2 Li(s) Ph-CEN (vii) (viii) then HCI, H20 HO (x) (1) DIBAL-H HO t-Bu, (ix) then NaOH, H20 p-TSOH (g) NH2 CH3 (xi) Но pyridine Но
10. The following reaction has variation of free energy value of AG = -2.1 kJ/mol CH;Br + H2S 2 CH;SH + HBr (a) Calculate Keq at room temperature (25°C) for this reaction as written. (b) Starting with a 1 M solution of CH3B and H2S, calculate the final concentrations of all four species at equilibrium.
Write the formula of reagents used in the following reactions:(i) Bromination of phenol to 2,4,6-tribromophenol(ii) Hydroboration of propene and then oxidation to propanol.(b) Arrange the following compound groups in the increasing order of their property indicated:(i) p-nitrophenol, ethanol, phenol (acidic character)(ii) Propanol, Propane, Propanal (boiling point)

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