S2018OrganicChemistryIMid-TermExam2Name(print):Name(Sign):RecitationInstructorName(sowecangetitbacktoyou):Instructions1.Keeptheexamcloseduntilyouareinstructedtobegin.2.Theexamconsistsof5questions.Thefirstthingyoushoulddoismakesurethatnopagesaremissing.Ifapageismissing,notifyaproctorimmediately.3.Youwillhave1hrand15minutestocompletetheexam,atwhichtimepencilsmustbeputdown.Budgetyourtimewisely.4.Makesuretoshowallofyourwork,andmakeitclearwhatyourthoughtprocesswas.Answersshouldfitinthespaceprovided.Ifyouneedtousethebackofthesheetofpaper,youmustmakenoteofitinthespaceallottedforcredit.

Breakdown

1.____/20

2.____/203.____/104._____/305._____/20

total_____/100

1)ReactionsPartA.Showtheproductsofthefollowingreactions.Chose5ofthe6,andmakesuretocirclethoseyouwantgraded.Ifyoudonotcircle,wewillgradethefirst5.(20points,4each)

Me Br2

H2O

CH2Br2

Zn

Br Mg(0)

Me MeNa/NH3

BH3; NaOOH

Br

NaNH2

E2

(A)

(B)

(C)

(D)

(E)

(F)

2).ReactionsPartB.Showthereagentsforthefollowingreactions.Chose5ofthe6,andmakesuretocirclethoseyouwantgraded.Ifyoudonotcircle,wewillgradethefirst5.(20points,4each)

OH

OH

O

O

O

Br

Br

Br

(A)

(B)

(C)

N3

3)ConceptQuestion.ThefollowingreactionsillustratetwodifferenteliminationproductsthatarisefromE2eliminationfromtwodifferentdiastereomers.Explainthisdifference,usingstructuresandmechanismstohelpsupportyouranswers(10points)

Br

Br NaNH2

NaNH2 major product

major product

4)Mechanisms.Showthemechanismof3ofthefollowing4reactions.Makesuretocirclethe3youwouldlikegraded.Otherwise,wewillgradethefirst3.(30points,10pointseach.

H2SO4

H2O

OH

(a)

4)Mechanisms(Continued)

MeH2SO4

H2O

Me OH

(b)

H2N NH(c)

Br2

heat

Br(d)

5)Synthesis.Proposeaseriesofreactionsthatwouldhelpcarryoutthefollowingsynthesis.(20points,10pointseach)(a)

CN

(b)