Question 1

Arrange the following compounds in increasing (weakest to strongest) order of basicity.

Accepted Answer

A)  IV < II < I < III 
B)  III < II < IV < I 
C)  II < I < III < IV 
D)  II < III < I < IV 
E)  None of the above 
A)  IV < II < I < III 
B)  III < II < IV < I 
C)  II < I < III < IV 
D)  II < III < I < IV 
E)  None of the above C

Question 2

What is the IUPAC name for the following compound?

Accepted Answer

7-amino-5-ethyl-1-hydroxy-3-octanone

Question 3

A compound with molecular formula C7H17N exhibits a triplet at $\delta$  1.0 (3H), a doublet at $\delta$  1.1 (I=6), a multiplet at $\delta$  2.0 (1H), a singlet at $\delta$  2.3 (3H), a doublet at $\delta$  2.3 (2H), and a quartet at $\delta$  2.4 (2H) in its 1H NMR spectrum. Its 13C NMR spectrum showed peaks at $\delta$  13.4, $\delta$  20, $\delta$  27.9, $\delta$  39.3, $\delta$  49.5 and $\delta$  65.2. What is the structure for this compound?

Accepted Answer

The answer of A compound with molecular formula C7H17N exhibits...

Question 4

Arrange the following compounds in decreasing (strongest to weakest) order of basicity.

Accepted Answer

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

Question 5

Provide a stepwise synthesis to carry out the following conversion.

Accepted Answer

@#IMG-DLM&_TB4454_00

Question 6

Predict the major product when p-toluidine reacts with sodium nitrite and hydrochloric acid at < 5°C followed by o-ethylphenol?
2

Accepted Answer

The answer of Predict the major product when p-toluidine reacts...

Question 7

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

1. @#IMG-DLM&_TB4454

Question 8

A compound with molecular formula C8H11N displays the following IR, 1H NMR and 13C NMR spectra. Propose a structure for this compound.   
 
SDBS

Accepted Answer

Question 9

Which of the following compounds is the strongest base?

Accepted Answer

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

Question 10

What is the IUPAC name for the following compound?

Accepted Answer

7-amino-5-

Question 11

What is the IUPAC name for the following compound?

Accepted Answer

A)  N-ethylhexanamine 
B)  N-ethylcyclohexanamine 
C)  N-cyclohexylethanamine 
D)  N-ethylcyclopentanamine 
E)  N-ethylaniline 
A)  N-ethylhexanamine 
B)  N-ethylcyclohexanamine 
C)  N-cyclohexylethanamine 
D)  N-ethylcyclopentanamine 
E)  N-ethylaniline

Question 12

Nicotine, present in tobacco, has the following structure. Which nitrogen is more basic and explain your choice.

Accepted Answer

N2 is more basic as

Question 13

Which one of the following is the best synthesis for 3,5-dibromotoluene?

Accepted Answer

A)  toluene, Br2/FeBr3 excess 
B)  1. p-toluidine, Br2/ FeBr3;
2) NaNO2/HCl, 3PO2 
C)  1. Toluene, HNO3/H2SO4
2) NH3
3) NaNO2/HCl, 3Cl/AlCl3 
E)  1. m-bromotoluene, HNO3, H2SO4
2) Fe/HCl
3) NaNO2/HCl, < 5°C
4) CuBr 
A)  toluene, Br2/FeBr3 excess 
B)  1. p-toluidine, Br2/ FeBr3;
2) NaNO2/HCl, 3PO2 
C)  1. Toluene, HNO3/H2SO4
2) NH3
3) NaNO2/HCl, 3Cl/AlCl3 
E)  1. m-bromotoluene, HNO3, H2SO4
2) Fe/HCl
3) NaNO2/HCl, < 5°C
4) CuBr

Question 14

Provide the reagents necessary to carry out the following conversion for the following reaction.

Accepted Answer

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

Question 15

What is the common name for the following compound?

Accepted Answer

A)  dibenzylamine 
B)  diphenylamine 
C)  dibenzeneamine 
D)  phenylbenzeneamine 
E)  none of these 
A)  dibenzylamine 
B)  diphenylamine 
C)  dibenzeneamine 
D)  phenylbenzeneamine 
E)  none of these

Question 16

What is the IUPAC name for the following compound?

Accepted Answer

A)  ethylisobutylisopropylamine 
B)  ethylisopropylbutylamine 
C)  sec-butylethylpropylamine 
D)  sec-butylethylisopropylamine 
E)  none of these 
A)  ethylisobutylisopropylamine 
B)  ethylisopropylbutylamine 
C)  sec-butylethylpropylamine 
D)  sec-butylethylisopropylamine 
E)  none of these

Question 17

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

Question 18

Predict the product for the following reaction.

Accepted Answer

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

Question 19

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

Question 20

Which of these alkyl halides cannot be used to prepare amines using Gabriel synthesis?

Accepted Answer

A)  1-bromopentane 
B)  1-bromo-3-methylbutane 
C)  2-bromo-3-methylpentane 
D)  1-bromo-2,3-dimethylbutane 
E)  2-bromo-2,3-dimethylbutane 
A)  1-bromopentane 
B)  1-bromo-3-methylbutane 
C)  2-bromo-3-methylpentane 
D)  1-bromo-2,3-dimethylbutane 
E)  2-bromo-2,3-dimethylbutane

Exam 22: Amines

Arrange the following compounds in increasing (weakest to strongest) order of basicity.

What is the IUPAC name for the following compound?

Arrange the following compounds in decreasing (strongest to weakest) order of basicity.

Provide a stepwise synthesis to carry out the following conversion.

Predict the major product when p-toluidine reacts with sodium nitrite and hydrochloric acid at < 5°C followed by o-ethylphenol? 2

Provide the reagents necessary to carry out the following conversion.

A compound with molecular formula C8H11N displays the following IR, 1H NMR and 13C NMR spectra. Propose a structure for this compound. SDBS

Which of the following compounds is the strongest base?

What is the IUPAC name for the following compound?

What is the IUPAC name for the following compound?

Nicotine, present in tobacco, has the following structure. Which nitrogen is more basic and explain your choice.

Which one of the following is the best synthesis for 3,5-dibromotoluene?

Provide the reagents necessary to carry out the following conversion for the following reaction.

What is the common name for the following compound?

What is the IUPAC name for the following compound?

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.

Which of these alkyl halides cannot be used to prepare amines using Gabriel synthesis?

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

Carboxylic Acids and Their Derivatives

Alpha Carbon Chemistry: Enols and Enolates

Introduction to Organometallic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

A compound with molecular formula C₈H₁₁N displays the following IR, ¹H NMR and ¹³C NMR spectra. Propose a structure for this compound. SDBS