Question 1

Provide a stepwise synthesis for the following compound using benzyl alcohol as your only source of carbon and using any other reagents necessary.

Accepted Answer

@#IMG-DLM&_TB4454_00 @#IMG-DLM&_TB4454_0

Question 2

Predict the product for the following reaction.

Accepted Answer

The answer of Predict the product for the following reaction....

Question 3

Barbital, used as a sedative, is synthesized from diethyl 2,2-diethyl malonate (A) and urea (B). Provide the structure for barbital.

Accepted Answer

The answer of Barbital, used as a sedative, is synthesized...

Question 4

Give the IUPAC name for glutaric acid.

Accepted Answer

A)  ethanedioic acid 
B)  propanedioic acid 
C)  butanedioic acid 
D)  pentanedioic acid 
E)  benzoic acid 
A)  ethanedioic acid 
B)  propanedioic acid 
C)  butanedioic acid 
D)  pentanedioic acid 
E)  benzoic acid

Question 5

What is the IUPAC name for the following compound?

Accepted Answer

A)  sec-butyl ethanoate 
B)  ethyl 3-methylpentanoate 
C)  3-methylbutyl ethanoate 
D)  ethyl 3-methylbutanoate 
E)  none of these 
A)  sec-butyl ethanoate 
B)  ethyl 3-methylpentanoate 
C)  3-methylbutyl ethanoate 
D)  ethyl 3-methylbutanoate 
E)  none of these

Question 6

A compound with molecular formula C8H14O3 exhibits a triplet at $\delta$ 1.0 (6H), a sextet at $\delta$ 1.6 (4H) and a triplet at $\delta$ 2.2 (4H) in its 1H NMR spectrum. Its IR spectrum shows two strong absorption bands near 1850 and 1750 cm-1. What is the structure for this compound?

Accepted Answer

The answer of A compound with molecular formula C8H14O3 exhibits...

Question 7

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

1. Mg/ethe

Question 8

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

The answer of Provide the reagents necessary to carry out...

Question 9

Rank the following acids in decreasing (strongest to weakest) order of acidity. Explain your choice.

Accepted Answer

II > IV > III > I
II: The nitro group is

Question 10

What is the common name for the following compound?

Accepted Answer

A)  ($\alpha$-bromobutyryl chloride) 
B)  ($\beta$-bromobutyryl chloride) 
C)  1-bromobutanoyl chloride 
D)  2-bromobutanoyl chloride 
E)  2-bromopropanoyl chloride 
A)  ($\alpha$-bromobutyryl chloride) 
B)  ($\beta$-bromobutyryl chloride) 
C)  1-bromobutanoyl chloride 
D)  2-bromobutanoyl chloride 
E)  2-bromopropanoyl chloride

Question 11

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

A)  NaBH4/CH3OH 
B)  Na/NH3 
C)  1. LiAlH4
2) H2O 
D)  H3O+/heat 
E)  A and C 
A)  NaBH4/CH3OH 
B)  Na/NH3 
C)  1. LiAlH4
2) H2O 
D)  H3O+/heat 
E)  A and C

Question 12

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

A)  1. LiAlH4
2) H2O 
B)  NaBH4/CH3OH 
C)  LiAl[OC(CH3)3]H 
D)  BH3·THF 
E)  C and D 
A)  1. LiAlH4
2) H2O 
B)  NaBH4/CH3OH 
C)  LiAl[OC(CH3)3]H 
D)  BH3·THF 
E)  C and D

Question 13

What is the common name for the following compound?

Accepted Answer

A)  2,2-dimethylbutanenitrile 
B)  3,3-dimethylbutanenitrile 
C)  ($\alpha$,$\alpha$-dimethylbutyronitrile) 
D)  ($\beta$,$\beta$-dimethylbutyronitrile) 
E)  ($\gamma$,$\gamma$-dimethylbutyronitrile) 
A)  2,2-dimethylbutanenitrile 
B)  3,3-dimethylbutanenitrile 
C)  ($\alpha$,$\alpha$-dimethylbutyronitrile) 
D)  ($\beta$,$\beta$-dimethylbutyronitrile) 
E)  ($\gamma$,$\gamma$-dimethylbutyronitrile)

Question 14

Predict the product for the following reaction

Accepted Answer

The answer of Predict the product for the following reaction...

Question 15

Predict the product for the following reaction.

Accepted Answer

The answer of Predict the product for the following reaction....

Question 16

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

1. Na₂Cr₂O₇/H

Question 17

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

A)  CH3Li 
B)  CH3MgBr 
C)  (CH3)2CuLi 
D)  1. Mg/ether
2) CH3Br 
E)  CH3OH 
A)  CH3Li 
B)  CH3MgBr 
C)  (CH3)2CuLi 
D)  1. Mg/ether
2) CH3Br 
E)  CH3OH

Question 18

Predict the product for the following reaction and provide a stepwise, curved arrow, mechanism for the formation of the product.

Accepted Answer

@#IMG-DLM&_TB4454_00 Mechanism

Question 19

Predict the product for the following reaction.

Accepted Answer

The answer of Predict the product for the following reaction....

Question 20

Predict the product for the following reaction.

Accepted Answer

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

Exam 20: Carboxylic Acids and Their Derivatives

Provide a stepwise synthesis for the following compound using benzyl alcohol as your only source of carbon and using any other reagents necessary.

Predict the product for the following reaction.

Barbital, used as a sedative, is synthesized from diethyl 2,2-diethyl malonate (A) and urea (B). Provide the structure for barbital.

Give the IUPAC name for glutaric acid.

What is the IUPAC name for the following compound?

A compound with molecular formula C8H14O3 exhibits a triplet at δ\deltaδ 1.0 (6H), a sextet at δ\deltaδ 1.6 (4H) and a triplet at δ\deltaδ 2.2 (4H) in its 1H NMR spectrum. Its IR spectrum shows two strong absorption bands near 1850 and 1750 cm-1. What is the structure for this compound?

Provide the reagents necessary to carry out the following conversion.

Provide the reagents necessary to carry out the following conversion.

Rank the following acids in decreasing (strongest to weakest) order of acidity. Explain your choice.

What is the common name for the following compound?

Provide the reagents necessary to carry out the following conversion.

Provide the reagents necessary to carry out the following conversion.

What is the common name for the following compound?

Predict the product for the following reaction

Predict the product for the following reaction.

Provide the reagents necessary to carry out the following conversion.

Provide the reagents necessary to carry out the following conversion.

Predict the product for the following reaction and provide a stepwise, curved arrow, mechanism for the formation of the product.

Predict the product for the following reaction.

Predict the product for the following reaction.

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

Synthesis

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

Alpha Carbon Chemistry: Enols and Enolates

Amines

Introduction to Organometallic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

A compound with molecular formula C₈H₁₄O₃ exhibits a triplet at $\delta$ 1.0 (6H), a sextet at $\delta$ 1.6 (4H) and a triplet at $\delta$ 2.2 (4H) in its ¹H NMR spectrum. Its IR spectrum shows two strong absorption bands near 1850 and 1750 cm^-1. What is the structure for this compound?