Question 1

Select the reagents necessary to convert cyclopentene into cyclopentane.

Accepted Answer

A) H2 and Ni 
B) H2O 
C) Heat 
D) Zn,H3O+ 
E) Light 
A) H2 and Ni 
B) H2O 
C) Heat 
D) Zn,H3O+ 
E) Light

Question 2

Which of the following pairs of compounds represent pairs of constitutional isomers?

Accepted Answer

A) 2-Methylbutane and pentane 
B) 2-Chlorohexane and 3-chlorohexane 
C) sec-Butyl bromide and tert-butyl bromide 
D) Propyl chloride and isopropyl chloride 
E) All of these choices. 
A) 2-Methylbutane and pentane 
B) 2-Chlorohexane and 3-chlorohexane 
C) sec-Butyl bromide and tert-butyl bromide 
D) Propyl chloride and isopropyl chloride 
E) All of these choices.

Question 3

What is the index of hydrogen deficiency (or degree of unsaturation)of a compound with the molecular formula of C11H20Br3F4N3O3?

Accepted Answer

A) 0 
B) 1 
C) 2 
D) 3 
E) 4 
A) 0 
B) 1 
C) 2 
D) 3 
E) 4

Question 4

What product is formed when cyclohexa-2,5-diene-1,4-diol is reacted with Pd/C and H2?

Accepted Answer

A) hexane-1,4-diol 2 
B) cyclohex-2-ene-1,4-diol 
C) cyclohexane-1,4-diol 
D) hexane-1,4-diol 
E) None of these choices. 
A) hexane-1,4-diol 2 
B) cyclohex-2-ene-1,4-diol 
C) cyclohexane-1,4-diol 
D) hexane-1,4-diol 
E) None of these choices.

Question 5

What is a correct name for the following compound?

Accepted Answer

A) 3-Isobutyl-2-methylheptane 
B) 3-sec-Butyl-2-methyloctane 
C) 5-Isobutyl-6-methylheptane 
D) 2-Ethyl-3-isopropyloctane 
E) 4-Isopropyl-3-methylnonane 
A) 3-Isobutyl-2-methylheptane 
B) 3-sec-Butyl-2-methyloctane 
C) 5-Isobutyl-6-methylheptane 
D) 2-Ethyl-3-isopropyloctane 
E) 4-Isopropyl-3-methylnonane

Question 6

Which of the following can be described as trans isomers?

Accepted Answer

A) I 
B) II,V 
C) III,IV 
D) I,III and IV 
E) None of these choices are trans isomers. 
A) I 
B) II,V 
C) III,IV 
D) I,III and IV 
E) None of these choices are trans isomers.

Question 7

Draw the bond-line structural formula corresponding to the name: trans-1,6-dichlorobicyclo[4.4.0]decane.

Accepted Answer

The answer of Draw the bond-line structural formula corresponding to...

Question 8

A correct name for the following compound is:

Accepted Answer

A) 2-Methylbicyclo[4.3.0]nonane 
B) 1-Methylbicyclo[4.3.1]nonane 
C) 7-Methylbicyclo[4.3.0]nonane 
D) 2-Methylbicyclo[4.3.1]nonane 
E) 1-Methylbicyclo[4.3.0]nonane 
A) 2-Methylbicyclo[4.3.0]nonane 
B) 1-Methylbicyclo[4.3.1]nonane 
C) 7-Methylbicyclo[4.3.0]nonane 
D) 2-Methylbicyclo[4.3.1]nonane 
E) 1-Methylbicyclo[4.3.0]nonane

Question 9

What is the index of hydrogen deficiency (or degree of unsaturation)of the following molecule?

Accepted Answer

A) 2 
B) 3 
C) 4 
D) 5 
E) 6 
A) 2 
B) 3 
C) 4 
D) 5 
E) 6

Question 10

Which conformation represents the most stable conformation of trans-1-bromo-4-methylcyclohexane?

Accepted Answer

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

Question 11

Unknown compound X was found to absorb two equivalents of hydrogen gas when subjected to catalytic hydrogenation conditions with Pd/C,and the chemical formula of the product was determined to be C4H10.If compound X was found to have a sharp IR absorption around 3300 cm-1 determine its structure.

Accepted Answer

Since the product has an IHD = 0 the com

Question 12

The most stable conformation of 2,3-dimethylpentane,viewed through the C-2-C-3 bond (i.e.,C-2 in the front,C-3 in the back):

Accepted Answer

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

Question 13

Provide a name for the following compound:

Accepted Answer

A) 1-Hydroxy-3-sec-butylcyclopentane 
B) 3-sec-Butyl-1-cyclopentanol 
C) 1-sec-Butyl-3-cyclopentanol 
D) 4-sec-Butyl-1-cyclopentanol 
E) 3-Isobutyl-1-cyclopentanol 
A) 1-Hydroxy-3-sec-butylcyclopentane 
B) 3-sec-Butyl-1-cyclopentanol 
C) 1-sec-Butyl-3-cyclopentanol 
D) 4-sec-Butyl-1-cyclopentanol 
E) 3-Isobutyl-1-cyclopentanol

Question 14

Neglecting stereochemistry,which of these common group names is ambiguous,i.e.,does not refer to one specific group?

Accepted Answer

A) Butyl 
B) sec-Butyl 
C) tert-Pentyl 
D) Neopentyl 
E) sec-Pentyl 
A) Butyl 
B) sec-Butyl 
C) tert-Pentyl 
D) Neopentyl 
E) sec-Pentyl

Question 15

What is the correct name of the following compound?

Accepted Answer

A) 1-Chlorobicyclo[4.1.1]octane 
B) 2-Chlorobicyclo[4.1.0]octane 
C) 2-Chlorobicyclo[4.1.1]octane 
D) 2-Chlorobicyclo[4.1.1]heptane 
E) 5-Chlorobicyclo[4.1.1]octane 
A) 1-Chlorobicyclo[4.1.1]octane 
B) 2-Chlorobicyclo[4.1.0]octane 
C) 2-Chlorobicyclo[4.1.1]octane 
D) 2-Chlorobicyclo[4.1.1]heptane 
E) 5-Chlorobicyclo[4.1.1]octane

Question 16

What product is formed when cis-2,3,3-trimethylhepta-1,5-diene is reacted with Pd/C and H2?

Accepted Answer

A) cis-5,5,6-trimethylhept-2-ene 2 
B) 2,3,3-trimethylhept-1-ene 
C) 5,5,6-trimethylheptane 
D) 2-isopropyl-2-methylhexane 
E) None of these choices. 
A) cis-5,5,6-trimethylhept-2-ene 2 
B) 2,3,3-trimethylhept-1-ene 
C) 5,5,6-trimethylheptane 
D) 2-isopropyl-2-methylhexane 
E) None of these choices.

Question 17

What product is formed when trans,trans-hepta-3,5-dien-1-yne is reacted with Pd/C and H2?

Accepted Answer

A) heptane 2 
B) 1-heptyne 
C) 1-ethylpentane 
D) trans-2-heptene 
E) None of these choices. 
A) heptane 2 
B) 1-heptyne 
C) 1-ethylpentane 
D) trans-2-heptene 
E) None of these choices.

Question 18

Eclipsed conformations are thermodynamically more unstable than staggered conformations due to steric repulsions.

Accepted Answer

A) True 
 B)False

Question 19

Draw the Newman projection formula for the most stable conformation of the C2-C3 bond in 3-methylpentane.

Accepted Answer

The answer of Draw the Newman projection formula for the...

Question 20

Which of these C10H18 isomers is predicted to be the most stable?

Accepted Answer

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

Exam 4: Nomenclature and Conformations of Alkanes and Cycloalkanes

Select the reagents necessary to convert cyclopentene into cyclopentane.

Which of the following pairs of compounds represent pairs of constitutional isomers?

What is the index of hydrogen deficiency (or degree of unsaturation)of a compound with the molecular formula of C11H20Br3F4N3O3?

What product is formed when cyclohexa-2,5-diene-1,4-diol is reacted with Pd/C and H2?

What is a correct name for the following compound?

Which of the following can be described as trans isomers?

Draw the bond-line structural formula corresponding to the name: trans-1,6-dichlorobicyclo[4.4.0]decane.

A correct name for the following compound is:

What is the index of hydrogen deficiency (or degree of unsaturation)of the following molecule?

Which conformation represents the most stable conformation of trans-1-bromo-4-methylcyclohexane?

Unknown compound X was found to absorb two equivalents of hydrogen gas when subjected to catalytic hydrogenation conditions with Pd/C,and the chemical formula of the product was determined to be C4H10.If compound X was found to have a sharp IR absorption around 3300 cm-1 determine its structure.

The most stable conformation of 2,3-dimethylpentane,viewed through the C-2-C-3 bond (i.e.,C-2 in the front,C-3 in the back):

Provide a name for the following compound:

Neglecting stereochemistry,which of these common group names is ambiguous,i.e.,does not refer to one specific group?

What is the correct name of the following compound?

What product is formed when cis-2,3,3-trimethylhepta-1,5-diene is reacted with Pd/C and H2?

What product is formed when trans,trans-hepta-3,5-dien-1-yne is reacted with Pd/C and H2?

Eclipsed conformations are thermodynamically more unstable than staggered conformations due to steric repulsions.

Draw the Newman projection formula for the most stable conformation of the C2-C3 bond in 3-methylpentane.

Which of these C10H18 isomers is predicted to be the most stable?

The Basics

Families of Carbon

Acids and Bases

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes I

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

What is the index of hydrogen deficiency (or degree of unsaturation)of a compound with the molecular formula of C₁₁H₂₀Br₃F₄N₃O₃?

What product is formed when cyclohexa-2,5-diene-1,4-diol is reacted with Pd/C and H₂?

What product is formed when cis-2,3,3-trimethylhepta-1,5-diene is reacted with Pd/C and H₂?

What product is formed when trans,trans-hepta-3,5-dien-1-yne is reacted with Pd/C and H₂?

Which of these C₁₀H₁₈ isomers is predicted to be the most stable?