Question 1

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 2

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 3

Propose an efficient synthesis of propanoic acid from acetylene:

Accepted Answer

The answer of Propose an efficient synthesis of propanoic acid...

Question 4

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)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) H2,Pt 
D) 1)BH3-THF;2)H2O2,NaOH 
E) 1)O3;2)DMS

Question 5

Predict the products of the following reaction:

Accepted Answer

A) I,III,and IV 
B) II,III,and IV 
C) I,III,and V 
D) II,IV,and VI 
E) III and IV 
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 6

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

Accepted Answer

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

Question 7

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

Accepted Answer

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

Question 8

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

Accepted Answer

The answer of Propose an efficient method of converting 3-methyl-1-butanol...

Question 9

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

Accepted Answer

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 
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 10

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

Accepted Answer

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

Question 11

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 12

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

Accepted Answer

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

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

Accepted Answer

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$\nu$ 
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 15

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

Accepted Answer

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

Exam 12: Synthesis

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

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

Propose an efficient synthesis of propanoic acid from acetylene:

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

Predict the products of the following reaction:

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

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

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

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

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

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

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

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

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

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

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

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