Deck 12: Synthesis

Question 1

Predict the reagent(s)required to complete the following transformation:

A)1)OsO₄;2)NaHSO₃,H₂O
B)1)Hg(OAc)₂,H₂O;2)NaBH₄
C)1)RCO₃H;2)H₃O⁺
D)H₂SO₄,H₂O
E)1)O₃;2)DMS

Answer 1

1)OsO₄;2)NaHSO₃,H₂O

Question 2

Predict the reagent(s)required to complete the following transformation:

A)1)OsO₄;2)NaHSO₃,H₂O
B)NaNH₂
C)H₂,Pt
D)Na,NH₃(l)
E)H₂,Lindlar's catalyst

Answer 2

H₂,Lindlar's catalyst

Question 3

Predict the major product(s)obtained from the following reaction:

A)I
B)II
C)III
D)IV
E)II and IV

Answer 3

III

Question 4

Provide the reagent(s)required to complete the following transformation:

A)HBr
B)Br₂/h $\nu$
C)Br₂/ROOR
D)HBr/ROOR
E)h $\nu$ /NBS

Question 5

Predict the reagent(s)required to complete the following transformation:

A)1)OsO₄;2)NaHSO₃,H₂O
B)1)Hg(OAc)₂,H₂O;2)NaBH₄
C)1)RCO₃H;2)H₃O⁺
D)H₂SO₄,H₂O
E)1)O₃;2)DMS

Question 6

Predict the reagent(s)required to complete the following transformation:

A)NaOtBu
B)HBr
C)H₂SO₄
D)NaOH
E)NaSH

Question 7

Predict the reagent(s)required to complete the following transformation:

A)NaOtBu
B)HBr
C)H₂SO₄
D)NaOH
E)NaSH

Question 8

Predict the reagent(s)required to complete the following transformation:

A)1)OsO₄;2)NaHSO₃,H₂O
B)1)Hg(OAc)₂,H₂O;2)NaBH₄
C)H₂,Pt
D)1)BH₃-THF;2)H₂O₂,NaOH
E)1)O₃;2)DMS

Question 9

Predict the reagent(s)required to complete the following transformation:

A)1)OsO₄;2)NaHSO₃,H₂O
B)1)Hg(OAc)₂,H₂O;2)NaBH₄
C)1)RCO₃H;2)H₃O⁺
D)H₂SO₄,H₂O
E)1)O₃;2)DMS

Question 10

Predict the reagent(s)required to complete the following transformation:

A)1)OsO₄;2)NaHSO₃,H₂O
B)1)Hg(OAc)₂,H₂O;2)NaBH₄
C)H₂,Pt
D)1)9-BBN;2)H₂O₂,NaOH
E)1)O₃;2)DMS

Question 11

Provide the reagent(s)required to complete the following transformation:

A)NaOH
B)heat/H₂SO₄
C)CH₃CO₂H
D)NaOEt
E)KOtBu

Question 12

Provide the reagent(s)required to complete the following transformation:

A)HBr
B)Br₂/H₂O
C)Br₂
D)HBr/ROOR
E)h $\nu$ /NBS

Question 13

Predict the reagent(s)required to complete the following transformation:

A)1)OsO₄;2)NaHSO₃,H₂O
B)1)Hg(OAc)₂,H₂O;2)NaBH₄
C)1)RCO₃H;2)H₃O⁺
D)1)BH₃-THF;2)H₂O₂,NaOH
E)1)O₃;2)DMS

Question 14

Provide the reagent(s)required to complete the following transformation:

A)HBr
B)Br₂/h $\nu$
C)Br₂/ROOR
D)HBr/ROOR
E)h $\nu$ /NBS

Question 15

Predict the major product(s)for the following transformation:

A)I
B)II
C)III
D)IV
E)I and III

Question 16

Provide the reagent(s)required to complete the following transformation:

A)HBr
B)Br₂/h $\nu$
C)Br₂
D)HBr/ROOR
E)h $\nu$ /NBS

Question 17

Predict the major product(s)for the following reaction:

A)I
B)II
C)III
D)IV
E)I and III

Question 18

Predict the reagent(s)required to complete the following transformation:

A)1)OsO₄;2)NaHSO₃,H₂O
B)NaNH₂
C)H₂,Pt
D)Na,NH₃(l)
E)H₂,Lindlar's catalyst

Question 19

Predict the reagent(s)required to complete the following transformation:

A)1)OsO₄;2)NaHSO₃,H₂O
B)1)Hg(OAc)₂,H₂O;2)NaBH₄
C)1)RCO₃H;2)H₃O⁺
D)1)BH₃-THF;2)H₂O₂,NaOH
E)1)O₃;2)DMS

Question 20

Predict the reagent(s)required to complete the following transformation:

A)1)OsO₄;2)NaHSO₃,H₂O
B)H₂SO₄,H₂O,HgSO₄
C)H₂,Pt
D)1)9-BBN;2)H₂O₂,NaOH
E)1)O₃;2)DMS

Question 21

Predict the major product(s)for the following reaction:

A)I
B)II
C)III
D)IV
E)II and III

Question 22

Predict the reagent(s)required to convert 1-bromo-1-methylcyclohexane to 1-bromo-2-methylcyclohexane.

A)1)KOtBu;2)HBr
B)1)NaOEt;2)HBr
C)1)NaOEt;2)HBr,ROOR
D)1)KOtBu;2)HBr,ROOR
E)Br₂,h $\nu$

Question 23

Which sequence of reagents will accomplish the following transformation?

A)1)KOtBu;2)HBr
B)1)NaOEt;2)HBr,ROOR
C)1)H₂SO₄,heat;2)Br₂,h $\nu$
D)1)NaOEt;2)HBr
E)both A and D work

Question 24

Propose an efficient synthesis of cyclopentanone from 1-methylcyclopentane:

Question 25

One compound is produced when acetylene is treated with the following reagents.What is the IUPAC name of this compound?

Question 26

Predict the reagent(s)required to complete the following reaction:

A)NaNH₂
B)1)O₃;2)H₂O
C)KMnO₄
D)1)BH₃-THF;2)H₂O₂,NaOH
E)H₂SO₄,H₂O

Question 27

Predict a correct sequence of reactants required to complete the following transformation in which propanal is the only carbon-containing product.

A)1)I; 2)III; 3)IV; 4)V; 5)II
B)1)VI; 2)IV; 3)IV; 4)VII; 5)V; 6)II
C)1)V; 2)II
D)1)I; 2)IV; 3)VI; 4)V; 5)II
E)none of the above are correct

Question 28

Predict the reagent(s)required to complete the following transformation:

A)1)OsO₄;2)NaHSO₃,H₂O
B)H₂SO₄,H₂O,HgSO₄
C)NaOH
D)xs NaNH₂
E)1)O₃;2)DMS

Question 29

Predict the reagent(s)required to convert 4,5-dimethylhex-2-yne to 4,5-dimethylhex-1-yne.

A)1)OsO₄;2)NaHSO₃,H₂O
B)HBr,ROOR
C)NaBr
D)1)xs NaNH₂;2)H₃O⁺
E)HBr

Question 30

Predict the products of the following reaction:

A)I,III,and IV
B)II,III,and IV
C)I,III,and V
D)II,IV,and VI
E)III and IV

Question 31

Predict the reagent(s)required to complete the following transformation:

A)1)OsO₄;2)NaHSO₃,H₂O
B)H₂SO₄,H₂O,HgSO₄
C)NaOH
D)xs NaNH₂
E)1)O₃;2)H₂O

Question 32

Predict the major product(s)for the reaction of pent-1-en-4-yne with sodium amide followed by reaction with bromoethane.

A)Hept-1-en-4-yne
B)Hept-6-en-3-yne
C)Hept-3-en-6-yne
D)Hept-4-en-1-yne

Question 33

Predict the reagent(s)required to complete the following transformation:

A)1)OsO₄;2)NaHSO₃,H₂O
B)HBr,ROOR
C)NaBr
D)xs NaNH₂
E)HBr

Question 34

Which sequence of reagents will accomplish the following transformation?

A)1)KOtBu;2)1-bromopropane
B)1)NaNH₂;2)1-bromopropane
C)1)NaNH₂;2)2-bromopropane
D)1)O₃;2)DMS
E)1)O₃;2)1-bromopropane

Question 35

Reaction of compound A (molecular formula = C₇H₁₂)with sodium amide followed by reaction with 1-bromobutane produces (CH₃)₂CHCH(CH₃)CC(CH₂)₃CH₃.What is the name of compound A?

A)2,3-dimethylnon-4-yne
B)2,2-dimethylpent-1-yne
C)3,4-dimethylpent-1-yne
D)4,4-dimethylhept-1-yne
E)1-heptyne

Question 36

Predict the reagent(s)required to complete the following transformation:

A)1)OsO₄;2)NaHSO₃,H₂O
B)ROOR,heat
C)NaOH
D)xs NaNH₂
E)1)O₃;2)H₂O

Question 37

Propose an efficient synthesis of propanoic acid from acetylene:

Question 38

Reaction of compound A (molecular formula = C₁₂H₂₂)with ozone followed by reaction with DMS produces only (CH₃)₃CCH₂CHO.Which of the following could be compound A?

A)cis-2,3,7,8-tetramethyloct-4-ene
B)trans-dodec-6-ene
C)4,4-dimethylpent-1-ene
D)cis-2,2,7,7-tetramethyloct-4-ene
E)2,2-dimethyldec-4-ene

Question 39

Compound X has molecular formula C₈H₁₀.Reaction of Compound X with excess ozone,followed by reaction with dimethyl sulfide and finally rinsing with water produces only the compounds shown below.Draw a possibility for Compound X that is consistent with these results.

Question 40

Identify the changes that must occur in transforming cis-2-butene into 2-butanol:

A)only the identity of the functional group(s)must change
B)only the carbon skeleton must change
C)only the location of the functional group(s)must change
D)only the identity and location of the functional group(s)must change
E)both the carbon skeleton and the identity of the functional group(s)must change

Question 41

Propose an efficient method of converting 3-methyl-2-butanol into 3-methyl-1-butanol.

Question 42

Which of the following sequences most efficiently converts 3-methyl-1-pentene into 3-bromo-3-methylpentane?

A)1)HBr;2)NaOH;3)HBr
B)1)Br₂,h $\nu$ ;2)H₂,Pt
C)1)H₂,Pt;2)Br₂,h $\nu$
D)1)NBS,h $\nu$ ;2)H₂,Pt
E)1)HBr,ROOR;2)NaOH;3)HBr

Question 43

Which of the following sequences efficiently converts 2-methylpropene and sodium acetylide into 3-methylbutanal?

A)1)HBr;2)NaCCH;3)O₃;4)H₂O
B)1)HBr;2)NaCCH;3)O₃;4)DMS
C)1)HBr,ROOR;2)NaCCH;3)O₃;4)H₂O
D)1)HBr,ROOR;2)NaCCH;3)H₂/Ni₂B 3)O₃;4)DMS
E)1)NaCCH;2)H₂/Ni₂B;3)O₃;4)DMS

Question 44

Propose an efficient method of completing the following transformation:

Question 45

What is the minimum number of steps required to convert 2-methylpropane into 1-bromo-2-methyl-2-propanol?

A)1
B)2
C)3
D)4
E)5

Question 46

Propose an efficient method of completing the following transformation:

Question 47

Which of the following provides an efficient method of converting 3-bromo-2-methyl-1-butene into 2-methyl-2-butene?

A)1)NaOH;2)H₂,Pt
B)1)H₂,Pt;2)NaOEt
C)1)H₂,Pt;2)xs NaNH₂
D)1)H₂,Ni₂B;2)KOtBu
E)1)H₂,Pt;2)KOtBu

Question 48

Propose a strategy to carry out the following transformation:

Question 49

Propose an efficient method of completing the following transformation:

Question 50

Propose an efficient method of converting 3-methyl-1-butanol into 3-methyl-2-butanol.

Question 51

Which order of alterations would most effectively transform trans-2-butene into 1-butene?

A)convert to the dibromoalkane,then to the terminal alkyne,then to the terminal alkene
B)convert to an alcohol,then to a terminal alkyne,finally to the terminal alkene
C)convert to the terminal alkene in one step
D)shorten the chain by two carbons,then add a two-carbon alkene to the end
E)convert to an alkane,then to a terminal alkyne,and finally to a terminal alkene

Question 52

Propose an efficient method of completing the following transformation:

Question 53

What is the minimum number of steps required to convert 2-methylpropane into 2-methylpropene?

A)1
B)2
C)3
D)4
E)5

Question 54

Propose an efficient synthesis of 1-butene from propyne:

Question 55

Which of the following alkenes cannot be converted into an alkyne by reaction with bromine followed by excess sodium amide and then with water?

A)I
B)II
C)III
D)IV
E)III and IV