Question 1

How would one used a Grignard-based synthesis to accomplish the following transformation? methyl isobutyrate [(CH₃)₂CHCO₂CH₃] to 3-ethyl-2-methylpentan-3-ol

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Question 2

Provide the structure of the major organic product in the reaction below.

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Question 3

Draw (2R, 3S) 2-bromopentan-1,3-diol in a Fischer projection.

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Question 4

Provide the name of the major organic product that results when 1-pentene is treated with aqueous acid.

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Question 5

Provide the major organic product of the following reaction.

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Question 6

________, also known as wood alcohol, is used as a fuel and as a solvent. Ingestion of this alcohol can lead to blindness and death.

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Question 7

Provide the major organic product of the reaction below.

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Question 8

Complete the following synthesis by providing the necessary sequence of reactants.

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Question 9

What is the correct IUPAC name for the following structure?

Accepted Answer

A)  (Z) 4-methyl-3-hexen-1-thiol 
B)  (Z) 6-mercapto-3-methylhex-3-ene 
C)  (
E)  6-mercapto-3-methylhex-3-ene 
D)  (
E)  4-methylhex-3-en-1-thiol

Question 10

What sequence of reagents is needed to convert 2-chlorobutane into 3-methyl-4-heptanol?

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Question 11

Provide an acceptable name for the compound below.

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Question 12

Which solvent is not suitable when running a reaction with a Grignard or organolithium reagent?

Accepted Answer

A)  DMSO 
B)  Tetrahydrofuran 
C)  Diethyl ether 
D)  Methanol

Question 13

Provide the structure of the major organic product in the reaction shown below.

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Question 14

When an aldehyde is treated with LiAlH4 followed by addition of H2O, what general class of product results?

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A)  primary alcohol 
B)  secondary alcohol 
C)  tertiary alcohol 
D)  ether 
E)  ketone

Question 15

In a 1-butanol molecule, what part of the molecule is described as hydrophobic?

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Question 16

Given the set of reactants below, complete the acid-base reaction, and indicate whether the equilibrium favors reactants or products using pKa values. CH₃CH₂O^- + NH₃

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Question 17

Provide a common name for the following structure.

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Question 18

What is the approximate pKa of phenols?

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Question 19

Name the major organic product which results when CH₃CO₂CH₂CH₃ is treated with 2 equivalents of (CH₃)₂CHMgBr followed by protonation with dilute acid?

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Question 20

Provide the major organic product(s) of the reaction below.

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Exam 10: Structure and Synthesis of Alcohols

How would one used a Grignard-based synthesis to accomplish the following transformation? methyl isobutyrate [(CH₃)₂CHCO₂CH₃] to 3-ethyl-2-methylpentan-3-ol

Provide the structure of the major organic product in the reaction below.

Draw (2R, 3S) 2-bromopentan-1,3-diol in a Fischer projection.

Provide the name of the major organic product that results when 1-pentene is treated with aqueous acid.

Provide the major organic product of the following reaction.

________, also known as wood alcohol, is used as a fuel and as a solvent. Ingestion of this alcohol can lead to blindness and death.

Provide the major organic product of the reaction below.

Complete the following synthesis by providing the necessary sequence of reactants.

What is the correct IUPAC name for the following structure?

What sequence of reagents is needed to convert 2-chlorobutane into 3-methyl-4-heptanol?

Provide an acceptable name for the compound below.

Which solvent is not suitable when running a reaction with a Grignard or organolithium reagent?

Provide the structure of the major organic product in the reaction shown below.

When an aldehyde is treated with LiAlH₄ followed by addition of H₂O, what general class of product results?

In a 1-butanol molecule, what part of the molecule is described as hydrophobic?

Given the set of reactants below, complete the acid-base reaction, and indicate whether the equilibrium favors reactants or products using pKa values. CH₃CH₂O^- + NH₃

Provide a common name for the following structure.

What is the approximate pKa of phenols?

Name the major organic product which results when CH₃CO₂CH₂CH₃ is treated with 2 equivalents of (CH₃)₂CHMgBr followed by protonation with dilute acid?

Provide the major organic product(s) of the reaction below.

Exam 10: Structure and Synthesis of Alcohols

How would one used a Grignard-based synthesis to accomplish the following transformation? methyl isobutyrate [(CH3)2CHCO2CH3] to 3-ethyl-2-methylpentan-3-ol

Provide the structure of the major organic product in the reaction below.

Draw (2R, 3S) 2-bromopentan-1,3-diol in a Fischer projection.

Provide the name of the major organic product that results when 1-pentene is treated with aqueous acid.

Provide the major organic product of the following reaction.

________, also known as wood alcohol, is used as a fuel and as a solvent. Ingestion of this alcohol can lead to blindness and death.

Provide the major organic product of the reaction below.

Complete the following synthesis by providing the necessary sequence of reactants.

What is the correct IUPAC name for the following structure?

What sequence of reagents is needed to convert 2-chlorobutane into 3-methyl-4-heptanol?

Provide an acceptable name for the compound below.

Which solvent is not suitable when running a reaction with a Grignard or organolithium reagent?

Provide the structure of the major organic product in the reaction shown below.

When an aldehyde is treated with LiAlH4 followed by addition of H2O, what general class of product results?

In a 1-butanol molecule, what part of the molecule is described as hydrophobic?

Given the set of reactants below, complete the acid-base reaction, and indicate whether the equilibrium favors reactants or products using pKa values. CH3CH2O- + NH3

Provide a common name for the following structure.

What is the approximate pKa of phenols?

Name the major organic product which results when CH3CO2CH2CH3 is treated with 2 equivalents of (CH3)2CHMgBr followed by protonation with dilute acid?

Provide the major organic product(s) of the reaction below.

How would one used a Grignard-based synthesis to accomplish the following transformation? methyl isobutyrate [(CH₃)₂CHCO₂CH₃] to 3-ethyl-2-methylpentan-3-ol

When an aldehyde is treated with LiAlH₄ followed by addition of H₂O, what general class of product results?

Given the set of reactants below, complete the acid-base reaction, and indicate whether the equilibrium favors reactants or products using pKa values. CH₃CH₂O^- + NH₃

Name the major organic product which results when CH₃CO₂CH₂CH₃ is treated with 2 equivalents of (CH₃)₂CHMgBr followed by protonation with dilute acid?