Question 1

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

Accepted Answer

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 
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 2

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

Accepted Answer

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

Question 3

Propose an efficient method of completing the following transformation:

Accepted Answer

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

Question 4

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

Accepted Answer

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 
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 5

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

Accepted Answer

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

Question 6

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

Accepted Answer

The answer of One compound is produced when acetylene is...

Question 7

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

Accepted Answer

A) NaOtBu 
B) HBr 
C) H2SO4 
D) NaOH 
E) NaSH 
A) NaOtBu 
B) HBr 
C) H2SO4 
D) NaOH 
E) NaSH

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) 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 9

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

Accepted Answer

A) NaOH 
B) heat/H2SO4 
C) CH3CO2H 
D) NaOEt 
E) KOtBu 
A) NaOH 
B) heat/H2SO4 
C) CH3CO2H 
D) NaOEt 
E) 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 reagent(s)required to convert 4,5-dimethylhex-2-yne to 4,5-dimethylhex-1-yne.

Accepted Answer

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

Question 12

Propose an efficient synthesis of 1-butene from propyne:

Accepted Answer

The answer of Propose an efficient synthesis of 1-butene from...

Question 13

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

Accepted Answer

A) NaOtBu 
B) HBr 
C) H2SO4 
D) NaOH 
E) NaSH 
A) NaOtBu 
B) HBr 
C) H2SO4 
D) NaOH 
E) NaSH

Question 14

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

Accepted Answer

A) Hept-1-en-4-yne 
B) Hept-6-en-3-yne 
C) Hept-3-en-6-yne 
D) Hept-4-en-1-yne 
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 15

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

Accepted Answer

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

Question 16

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.

Accepted Answer

Question 17

Propose an efficient synthesis of cyclopentanone from 1-methylcyclopentane:

Accepted Answer

The answer of Propose an efficient synthesis of cyclopentanone from...

Question 18

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?

Accepted Answer

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 
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 19

Which sequence of reagents will accomplish the following transformation?

Accepted Answer

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 
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 20

Propose a strategy to carry out the following transformation:

Accepted Answer

The answer of Propose a strategy to carry out the...

Exam 12: Synthesis

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

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

Propose an efficient method of completing the following transformation:

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

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

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

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:

Propose an efficient method of completing the following transformation:

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

Propose an efficient synthesis of 1-butene from propyne:

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

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

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

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.

Propose an efficient synthesis of cyclopentanone from 1-methylcyclopentane:

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?

Which sequence of reagents will accomplish the following transformation?

Propose a strategy to carry out 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

Lipids

Synthetic Polymers

Filters

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.

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?