Question 1

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

Accepted Answer

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

Question 2

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

Accepted Answer

The answer of Propose an efficient method of converting 3-methyl-2-butanol...

Question 3

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?

Accepted Answer

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 
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 D

Question 4

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

Accepted Answer

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

Question 5

Which sequence of reagents will accomplish the following transformation?

Accepted Answer

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 
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 6

Propose an efficient method of completing the following transformation:

Accepted Answer

The answer of Propose an efficient method of completing the...

Question 7

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

Accepted Answer

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

Question 8

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

Accepted Answer

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 
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 9

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

Accepted Answer

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 
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 10

Propose an efficient method of completing the following transformation:

Accepted Answer

The answer of Propose an efficient method of completing the...

Question 11

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

Accepted Answer

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

Question 12

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

Accepted Answer

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 
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 13

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

Accepted Answer

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

Question 14

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

Accepted Answer

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

Question 15

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

Accepted Answer

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 
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 16

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

Accepted Answer

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 
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 17

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

Accepted Answer

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

Question 18

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

Accepted Answer

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 
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 19

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

Accepted Answer

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

Question 20

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

Accepted Answer

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 
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

Exam 12: Synthesis

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

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

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?

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

Which sequence of reagents will accomplish the following transformation?

Propose an efficient method of completing the following transformation:

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

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

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

Propose an efficient method of completing the following transformation:

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

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

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

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

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

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

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

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

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

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

A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Substitution Reactions

Alkenes: Structure and Preparation Via Elimination Reactions

Addition Reactions of Alkenes

Alkynes

Radical Reactions

Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides

Nuclear Magnetic Resonance Spectroscopy

Infrared Spectroscopy and Mass Spectrometry

Conjugated Pi Systems and Pericyclic Reactions

Aromatic Compounds

Aromatic Substitution Reactions

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Alpha Carbon Chemistry: Enols and Enolates

Amines

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

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?