Question 1

Select the best reagents for the reaction below.

Accepted Answer

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

Question 2

Select the best reagents for the reaction below.

Accepted Answer

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

Question 3

Devise a method of converting 4-methyl-1-pentene into 3-methylbutanoic acid.

Accepted Answer

The answer of Devise a method of converting 4-methyl-1-pentene into...

Question 4

Propose a three-step synthetic sequence to accomplish the transformation below.

Accepted Answer

1. TsCl
2.

Question 5

Select the best reagents for the reaction below.

Accepted Answer

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

Question 6

Which of the following sequences 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 4. O3; 5. 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 4. O3; 5. DMS 
E)  1. NaCCH; 2. H2/Ni2B; 3. O3; 4. DMS

Question 7

Using retrosynthetic synthesis, determine which compound(s) could lead to the alkane shown below in a single step.

Accepted Answer

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

Question 8

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 9

The following sequence of reactions transforms acetylene into a compound with an altered carbon skeleton (compound 1), and from that into a compound in which the functional group has been changed (compound 2). Identify compounds 1 and 2.

Accepted Answer

A)  Compound 1 = I; Compound 2 = III 
B)  Compound 1 = II; Compound 2 = III 
C)  Compound 1 = VI; Compound 2 = IV 
D)  Compound 1 = II; Compound 2 = IV 
E)  Compound 1 = II; Compound 2 = V 
A)  Compound 1 = I; Compound 2 = III 
B)  Compound 1 = II; Compound 2 = III 
C)  Compound 1 = VI; Compound 2 = IV 
D)  Compound 1 = II; Compound 2 = IV 
E)  Compound 1 = II; Compound 2 = V

Question 10

Propose a synthesis of 1-butene from propyne.

Accepted Answer

The answer of Propose a synthesis of 1-butene from propyne....

Question 11

Devise a method of converting acetylene into the polymer shown below.

Accepted Answer

The answer of Devise a method of converting acetylene into...

Question 12

Select the best reagents for the reaction below.

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 13

2-Methylpentane (C6H14) can be converted, through a multistep synthesis, to a compound with a molecular formula of C6H13Br that shows exactly six resonances in its proton-decoupled 13C NMR spectrum. Suggest a synthetic pathway to prepare such a compound from 2-methylpentane.

Accepted Answer

Question 14

Identify the solvent that is not recommended for Green Chemistry.

Accepted Answer

A)  methylene chloride 
B)  water 
C)  ethanol 
D)  methanol 
E)  ethyl acetate 
A)  methylene chloride 
B)  water 
C)  ethanol 
D)  methanol 
E)  ethyl acetate

Question 15

Propose a synthesis to produce the following answer as one of the major products.

Accepted Answer

1. NBS, h@#LAT-DLM&
2. H<sub>2

Question 16

Select the best reagents for the reaction below.

Accepted Answer

A)  HBr 
B)  Br2/H2O 
C)  Br2, CCl4 
D)  HBr/ROOR 
E)  h$\upsilon$ /NBS 
A)  HBr 
B)  Br2/H2O 
C)  Br2, CCl4 
D)  HBr/ROOR 
E)  h$\upsilon$ /NBS

Question 17

Starting with a primary alkyl bromide, which of the following results in an overall increase in the length of the carbon skeleton by one carbon?

Accepted Answer

A)  substitute bromide with acetylide, then cleave the triple bond 
B)  substitute bromide with acetylide, then reduce the alkyne to an alkene 
C)  substitute bromide with methoxide 
D)  eliminate hydrogen bromide to produce an alkene 
A)  substitute bromide with acetylide, then cleave the triple bond 
B)  substitute bromide with acetylide, then reduce the alkyne to an alkene 
C)  substitute bromide with methoxide 
D)  eliminate hydrogen bromide to produce an alkene

Question 18

Devise a synthetic route of the compound shown below starting with 4-methyl-2-pentanol.

Accepted Answer

The answer of Devise a synthetic route of the compound...

Question 19

Starting with a primary alkyl bromide, which of the following results in an overall decrease in the length of the carbon skeleton by one carbon?

Accepted Answer

A)  substitute bromide with acetylide, then cleave the triple bond 
B)  substitute bromide with acetylide, then reduce the alkyne to an alkene 
C)  substitute bromide with methoxide 
D)  eliminate hydrogen bromide to produce an alkene, then cleave the double bond 
A)  substitute bromide with acetylide, then cleave the triple bond 
B)  substitute bromide with acetylide, then reduce the alkyne to an alkene 
C)  substitute bromide with methoxide 
D)  eliminate hydrogen bromide to produce an alkene, then cleave the double bond

Question 20

Devise a synthetic route for the following equation.

Accepted Answer

The answer of Devise a synthetic route for the following...

Exam 11: Synthesis

Select the best reagents for the reaction below.

Select the best reagents for the reaction below.

Devise a method of converting 4-methyl-1-pentene into 3-methylbutanoic acid.

Propose a three-step synthetic sequence to accomplish the transformation below.

Select the best reagents for the reaction below.

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

Using retrosynthetic synthesis, determine which compound(s) could lead to the alkane shown below in a single step.

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

The following sequence of reactions transforms acetylene into a compound with an altered carbon skeleton (compound 1), and from that into a compound in which the functional group has been changed (compound 2). Identify compounds 1 and 2.

Propose a synthesis of 1-butene from propyne.

Devise a method of converting acetylene into the polymer shown below.

Select the best reagents for the reaction below.

2-Methylpentane (C6H14) can be converted, through a multistep synthesis, to a compound with a molecular formula of C6H13Br that shows exactly six resonances in its proton-decoupled 13C NMR spectrum. Suggest a synthetic pathway to prepare such a compound from 2-methylpentane.

Identify the solvent that is not recommended for Green Chemistry.

Propose a synthesis to produce the following answer as one of the major products.

Select the best reagents for the reaction below.

Starting with a primary alkyl bromide, which of the following results in an overall increase in the length of the carbon skeleton by one carbon?

Devise a synthetic route of the compound shown below starting with 4-methyl-2-pentanol.

Starting with a primary alkyl bromide, which of the following results in an overall decrease in the length of the carbon skeleton by one carbon?

Devise a synthetic route for the following equation.

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

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

Addition Reactions of Alkenes

Alkynes

Radical Reactions

Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

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

Introduction to Organometallic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

2-Methylpentane (C₆H₁₄) can be converted, through a multistep synthesis, to a compound with a molecular formula of C₆H₁₃Br that shows exactly six resonances in its proton-decoupled ¹³C NMR spectrum. Suggest a synthetic pathway to prepare such a compound from 2-methylpentane.