1 CrO3, acidic medium B 1) SOCl2,

1 Surname and Initials Student Number 45 Organic Chemistry II (AAOCH2A/AAOCA2B/AAOCC2B) 20 October 2017 Test 3 QUESTION 1 5 Select the correct answer to each question from 1.1 to 1.

5 and write the corresponding letter in the block at the end of each question. 1.1 Which of the following transformations represents a reduction reaction: 1.2 Identify the reagents that you would need to accomplish the following transformation: A 1) H3O+, heat 2) CrO3, acidic medium B 1) SOCl2, pyridine 2) CH3CH2OH 3) Na2Cr2O7, acidic medium C 1) CH3CH2MgBr 2) H2O 3) Na2Cr2O7, acidic medium B 1) LiAlH4, ether 2) H3O+ 3) CH3CH2OH 1.3 Treatment of the following compound with NaBH4 will result in the formation of cyclohexanol: 1.

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4 Choose the correct reagents to give the following transformation: A 1) SO3 2) H2SO4 B 1) HNO3/H2SO4 2) SnCl2/H3O+ 3) NaOH C 1) CH3CH2Cl/AlCl3 2) KMnO4/H3O+ D 1) Br2/FeBr3 2) KMnO4/H3O+ 3) NaOH 1.5 Which of the following aromatic compounds will contain 7 carbon atoms? A toluene B phenol C o-xylene D aniline OOOABCD CH3CH2CHOCH3CH2CCH2CH3O CHOOCNH2OCOOHABCD NH22 QUESTION 2 8 2.1 Give the systematic IUPAC names of the following organic compounds: 2.1.1 ______________________________________ (1) 2.

1.2 (remember stereoisomerism!!) ______________________________________ (1) 2.1.3 ______________________________________ (1) 2.1.4 ______________________________________ (1) 2.1.

5 ____________________________________ (1) 2.1.6 _____________________________________ (1) 2.

1.7 _____________________________________ (1) 2.1.8 _____________________________________ (1) H3CBr HOHHOH BrBrOH OH OH HOCH2CHCH2OHOH COH OH3 QUESTION 3 10 Identify the reagents necessary to accomplish each of the following transformations: (a) (b) (c) (d) (e) (f) (g) (h) (i) (j) QUESTION 4 8 4.1 During the monochlorination of methane a free-radical mechanism is used.

A free-radical mechanism always involves THREE steps. State the three steps and write reaction equations to indicate them. (12 x ½) (6) (g)(h)(i)(j)COHOSO3Hacetophenonechlorobenzene(a)(b)(c)(d)(e)(f)4 4.2 This is not a very good method of preparing an alkylhalide. Briefly explain why. (2) QUESTION 5 5 For each of the following (5.

1-5.5), select the BEST method to produce the required product. Draw a circle around the method that you will select. 5.

1 5.2 5.3 5.4 5.5 OHH2OHg(OAc)2NaBH4BH3THFH2O2NaOH IOOAcOOAcOAcCH3CH2CH2OHCrO3/H3O+CH3CH2COOH CH3CCCH3H2Lindlar catalystNaNH3H3CCCHCH3H OHOHKMnO4/H3O+KMnO4/OH- CH3CCH2CH2COOHOCH3CHCH2CH2COOHOHNaBH4ethanolH3O+LiAlH4etherH3O+5 QUESTION 6 5 Provide the products of the following reactions: 6.

1 6.2 6.3 6.4 6.5 QUESTION 7 9 Each of the following syntheses requires more than one step.

How would you carry them out? 7.1 (5) 7.2 (4) CH3CHCH2ClCH3Mgether OCH3MgBrH2O CH3CCH3OPCC CH3CCCH2CH3O3Zn/H+ CH3CH2CH2COHONaBH4EthanolH3O+ HCCHCH3CH2CH2CHCH3OH H3COHCH36 TOTAL: 50 FULL MARKS: 45

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