ORG CHEM II 2nd EXAM NAME

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1 G EM II 2nd EXAM AME 1) Which of the following combinations is correct? Aldehydes... i. are more reactive than ketones towards nucleophiles ii. are more easily oxidized than ketones iii. are less reactive than ketones towards nucleophiles iv. are less easily oxidized than ketones a) i and iv b) i and ii c) iii and iv d) ii and iii e) none are correct 2) Which of the following amines would not form an imine with acetaldehyde? a) 32 b) 322 c) (3)2 d) all form imines e) none form imines 3) Which of the following compounds is an acetal? i. ii. iii. iv. a) i b) ii c) iii d) iv e) none are acetals 4) Dissolving benzaldehyde in methyl alcohol with catalytic acid establishes an equilibrium with what compound(s)? i. ii. iii. a) i. b) ii. c) iii d) i and ii e) i and iii 5) The LiAl4 reduction of esters is not a good route for the preparation of aldehydes because... a) LiAl4 is a powerful Lewis acid and will first react with the carbonyl oxygen b) LiAl4 is not able to react with the much less reactive ester carbonyl c) LiAl4 also rapidly reduces the aldehyde as it is formed, resulting in alcohols d) LiAl4 is a strong base and forms the enolate anion e) the statement above is incorrect, LiAl4 + ester is a good route to aldehydes 6) Which of the following statements is not true of the Williamson ether synthesis a) The rate of the reaction depends on the leaving group b) The rate of the reaction is proportional to the concentration of the nucleophile. c) The mechanism involves one concerted step. d) earrangements occur in some situations. e) All the above are correct 7) Which of the following is not an intermediate in the acid catalyzed formation of benzaldehyde dimethyl acetal from benzaldehyde and methanol? i ii iii iv a) i b) ii c) iii d) iv e) all are intermediates

2 8) The reaction of a primary amine with an aldehyde or ketones can mechanistically be viewed as: a) an addition followed by a substitution with water b) a substitution followed by an elimination of water c) an elimination of water followed by an addition d) an addition followed by an elimination of water e) primary amines do not react with aldehydes or ketones 9) The carbonyl carbon of an aldehyde or ketone is susceptible to electrophilic attack because: a) the carbon has a partial negative charge b) the carbon has a partial positive charge c) the double bond is easily polarized d) the above statement is correct, but, the correct reason is not given e) the above statement is incorrect, the carbon is subject to nucleophilic attack 10) Acetals are particularly useful as "protecting groups" for ketones or aldehydes. Acetals are inert to each of the following reagents except one. Which one? a) 3MgBr b) a2 c) 2S4 d) LiAl4 e) acetals react with all 11) Which of the following does not readily undergo oxidation with hromium oxide (r3), and sulfuric acid to give a carbonyl compound? a) n-butyl alcohol b) 2-methyl-1-propanol c) 2-butanol d) 2-methyl-2-propanol e) none of the above 12) Which of the following is not an intermediate in the reaction below. 2 S 4 (cat) a) b) c) 2 2 d) they are all intermediates e) none of the above are intermediates 13) Which of the following could be used to convert a primary alcohol to an aldehyde? a) P/2L2 b) KMn4/2 c) r3/l d) all of above e) none of above 14) In nucleophilic ring opening reactions of epoxides, the nucleophile is found to attack: a) the less substituted carbon of the epoxide b) the more substituted carbon of the epoxide c) the carbon-carbon bond of the epoxide d) the oxygen of the epoxide e) Epoxides are not effected by nucleophiles. i.e. no reaction takes place

3 15) The reaction below can be described as an Br + a 1,2-epoxypropane a) acid-base reaction followed by an intramolecular S1 reaction b) acid-base reaction followed by an intramolecular S2 reaction c) elimination reaction followed by an addition reaction d) addition reaction followed by an elimination reaction e) elimination reaction followed by an oxidation reaction 16) Select the right combination of reagents to synthesize isopropyl propyl ether via the Williamson ether synthesis. a) (3)2 + a followed by 322Br b) (3)2 + a followed by 322 c) a followed by (3)2Br d) a followed by (3)2 e) none of the above methods are suitable 17) In the acid catalyzed ring-opening of epoxides, the nucleophile attacks the: a) the less substituted carbon of the epoxide b) the more substituted carbon of the epoxide c) the carbon-carbon bond of the epoxide d) the oxygen of the epoxide e) Epoxides are not effected by acids. i.e. no reaction takes place 18) The - π-bond of an aldehyde or ketone is formed by overlap of which two orbitals? a) sp-sp b) sp 2 -sp 2 c)sp 2 -sp d) 2p-2p e)2s-2s 19) The following two carbonyl compounds react with the t-butyl grignard reagent at very different rates. ircle the compound that would react fastest and suggest two reasons why MgX 3 vs MgX 3 A The aldehyde B will react faster than the ketone A. Explanation 1: Electronic Effects Ketones: Inductive stabilization of electron defficient carbonyl carbon by two adjacent carbon groups. B Explanation 2: Steric Effects Aldehydes: Stabilization of the carbonyl group by only one carbon group...less stable than ketone, thus more reactive than ketone. ucmore steric henderance Slower ate uc- less steric henderance igher ate 20. ame the following compounds using IUPA (AS) nomenclature. Br Bromo-3,4-epoxy-1-pentanol

4 hydroxy-2-(1-methylpropyl)pentanal 1-cyclohexen-3-onecarbaldehyde 21. Describe why the following reaction won t work as predicted,and show the appropriate reactions that would allow the transformation to be done. 2 3 MgBr ether 3 The compound contains two fucntional groups (alcohol and aldehyde) beside the ester which will react with the grignard reagent. They must be protected, the reaction carried out, then deprotected MgBr ether 3 3 Si l 3 3 pyridine TMS 3 1) 2eq 3 MgX 2) Show the reagents needed to convert hexanal into hexane under each of the following conditions a. neutral p + S S remove 2 S S aney i ethanol 7 16 b. acidic p Zn, l 7 16 c. basic p 2 2 K Show the product and mechanism for the reaction shown below I - r.t I I - 3

5 24. Show the product and mechanism for each of the following reactions. a proton 3 2 transfer b MgBr 3 dry c proton 2 transfer ) Give the major organic product(s) for each of the following reactions. Show all relevant stereochemistry. 2 disiam 2 2 -, 2-2 +, P= PΦ 3 TF 2 3

6 l Ag(3) 2 Li( 3 ) 2 u TF S S + remove 2 1) a 2) 3 2 -Br I I 1) ab 4 2) 3 + 1) DIBA, TF 2) , K 1) 3 2) Zn, + KMn 4 +, heat 1) 3 2) 3 MgBr 3) 3 + 1) B 3 2) 2 2, - Pl 3 pyridine Sl 2 pyridine I 3 I l

7 3 1) g(ac) 2 3 2) ab 4 Zn, l 3 3 ( 3 ) 2 + ( 3 ) Write the reagents necessary to effect the following transformations 1) m-pba a) 2) - 2, Pt/ Quinoline b) l or 1) Li[(Me) 3 Al] 2) , c) d) 2 P 27. Propose a multistep synthesis of the transformations shown below a) 3 Br 2, hν 3=Pφ 3 Br 1) 3-2) 3 + r 3 2 S 4 b) l m-pba All BS Br 3 K 2 peroxides

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