CHEM210 [ CHAPTER 11 - ALKYNES]

1.GivetheIUPACnameforthefollowingcompound.

CH3C(CH3)2CH2C
CCH2CH(CH2CH2CH3)CH3

A)2,2,7trimethyl4undecyne
B)2,2,7trimethyl4nonyne
C)3,3,7trimethyl4decyne
D)2,2,7trimethyl4decyne
E)2,2,6trimethyl4undecyne

2.GivetheIUPACnameforthefollowingcompound.

CH3C
CCH2C(CH3)3

A)4,4dimethyl2hexyne
B)5,5dimethyl2hexyne
C)5,5dimethyl3hexyne

3.Rankthefollowingcompoundsinorderofincreasingbasicity.

A)a<b<cD)b<a<c
B)b<c<aE)c<b<a
C)c<a<b

4.Whichofthecircledhydrogensistheleastacidic?

CHEM210 [ CHAPTER 11 - ALKYNES]

5.Determinetheproductofthefollowingreaction.

6.Determinetheproductofthefollowingreaction.

7.Determinetheproductofthefollowingreaction.

CHEM210 [ CHAPTER 11 - ALKYNES]

8.Determinetheproduct(s)ofthefollowingreaction.

9.Determinetheproductofthefollowingreaction.

10.Determinetheproductofthefollowingreaction.

CHEM210 [ CHAPTER 11 - ALKYNES]

11.Determinetheproductofthefollowingreaction.

12.Determinetheproductofthefollowingreaction.

13.Determinetheproduct(s)ofthefollowingreaction.

CHEM210 [ CHAPTER 11 - ALKYNES]

14.Whatisthestartingmaterialinthereactionbelow?

15.Whatisthereagentforthefollowingreaction?

A)SOCl2D)Cl2
B)2HClE)Br2/CCl4
C)2TsCl

16.Whichofthefollowingisaketoenoltautomericpair?

17.ConsiderthedicarbonylcompoundAdrawnbelow.Whichofthefollowingcompoundscanbeanenoltautomerof
A?

A)aonlyD)aandb
B)bonlyE)aandc
C)conly

CHEM210 [ CHAPTER 11 - ALKYNES]

18.Whichofthefollowingcompoundsis(are)atautomerofcompoundAdrawnbelow?

A)a
B)b
C)c
D)CompoundsaandbarebothtautomersofA.
E)Compoundsa,bandcarealltautomersofA.

19.Whichofthefollowinganionsismostbasic?
A)CH3D)HC
C

B)H2C
CH E)CH3C
C

C)(CH3)3C

20.IntheadditionofHBrto1butyne,theelectrophileis:
A)theCspHsbondof1butyne.
B)theCCtriplebondof1butyne.
C)H+ion.
D)Brion.
E)theC2carbonatomof1butyne.

21.PredictthemajorproductBfromthereactionsequenceshownbelow.

A)ButaneD)2butyne
B)Cis2buteneE)1butyne
C)Trans2butene

22.Whichmethodwouldworkthebestincarryingoutthefollowingconversion?
A)(1)HBr;(2)2NaNH2
B)(1)Br2;(2)2NaNH2
C)(1)Br2,H2O;(2)NaNH2
D)(1)BH3,THF;(2)H2O2,NaOH;(3)NaNH2
E)(1)NaNH2

CHEM210 [ CHAPTER 11 - ALKYNES]

23.Howwouldyoucarryoutthefollowingconversion:

A)(1)H2O,H2SO4/HgSO4;(2)H2,Pt,
B)(1)HBr;(2)H2,Pt;(3)NaOH
C)(1)H2,Lindlarcatalyst;(2)BH3,THF;(3)H2O2,NaOH
D)(1)HBr,peroxides;(2)NaOH;(3)H2,Pt
E)(1)AqueousH2SO4

24.Whatistherelationshipbetweentheketoandenolformsofacetone,CH3COCH3?
A)Samecompounds
B)Diastereoisomers
C)Conformationalisomers
D)Constitutionalisomers
E)Resonancestructures

ChallengeQuestions
25.Terminalalkynescanbeconvertedtoacetylideionswithastrongbase.Determinetheproductfromthefollowing
reactionsequenceusedinthesynthesisofSpirastrellolideB.Note:THPandBnareusedasprotectinggroups
forthealcoholmoietiesandcanbeignoredforthepurposeofdeterminingtheanswertothisquestion.

26.ProvideanIUPACnameforthefollowingcompound.

A)(2R,3S,4R)4benzyl3fluoro5heptyn2ol
B)(2S,3R,4R)4benzyl3fluoro5heptyn2ol
C)(2S,3R,4S)3fluoro4phenyl5heptyn2ol
D)(2R,3S,4R)3benzyl4fluoro2heptyn5ol
E)(2S,3R,4S)3benzyl4fluoro2heptyn5ol

CHEM210 [ CHAPTER 11 - ALKYNES]

27.Determinewhichofthereagentsbelowisnotusedinthesynthesisofthetargetalcoholfromethyne.

28.Anaqueoussolutionofformicacidcanbeusedtopromotearingclosingreaction.Thinkaboutapossible
mechanismforthisreactionanddeterminethestructureoftheproduct.

29.Identifytheproductthatresultsfromthefollowingsequenceofreactions.

CHEM210 [ CHAPTER 11 - ALKYNES]

AnswerKeyChapter11:Alkynes

1.D
2.B
3.A
4.E
5.D
6.A
7.C
8.A
9.E
10.A
11.B
12.B
13.B
14.A
15.B
16.C
17.E
18.D
19.C
20.C
21.C
22.B
23.C
24.D
25.C
26.A
27.D
28.B
29.E