Question 1

Give the IUPAC name for the following compound.

Accepted Answer

A)  3-sec-Butyl-1,4-octadiyne 
B)  3-Isopropyl-1,5-octadiyne 
C)  3-Isopropyl-1,5-nonadiyne 
D)  3-sec-Butyl-1,4-nonadiyne 
A)  3-sec-Butyl-1,4-octadiyne 
B)  3-Isopropyl-1,5-octadiyne 
C)  3-Isopropyl-1,5-nonadiyne 
D)  3-sec-Butyl-1,4-nonadiyne

Question 2

Give the IUPAC name for the following compound.

Accepted Answer

A)  trans-2-Acetylenecyclohexanol 
B)  trans-2-Ethynylcyclohexanol 
C)  trans-2-Acetylene-1-cyclohexanol 
D)  trans-2-Ethylenecyclohexanol 
A)  trans-2-Acetylenecyclohexanol 
B)  trans-2-Ethynylcyclohexanol 
C)  trans-2-Acetylene-1-cyclohexanol 
D)  trans-2-Ethylenecyclohexanol

Question 3

What is the major organic product of the following reaction?

Accepted Answer

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

Question 4

Which of the following represents a keto-enol tautomeric pair?

Accepted Answer

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

Question 5

What is (are) the major organic product(s) of the following reaction?

Accepted Answer

A)  Only I and II 
B)  Only II and III 
C)  Only I and III 
D)  I, II, III 
A)  Only I and II 
B)  Only II and III 
C)  Only I and III 
D)  I, II, III

Question 6

What is (are) the product(s) of the following reaction?

Accepted Answer

A)  Only I 
B)  Only II 
C)  Only III 
D)  I, II, III 
A)  Only I 
B)  Only II 
C)  Only III 
D)  I, II, III

Question 7

What is the product of the following reaction?

Accepted Answer

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

Question 8

What is the major organic product of the following reaction?

Accepted Answer

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

Question 9

What is the reagent required to accomplish the following transformation?

Accepted Answer

A)  SOCl2 
B)  2eq. HCl 
C)  Cl2 
D)  Br2/CCl4 
A)  SOCl2 
B)  2eq. HCl 
C)  Cl2 
D)  Br2/CCl4

Question 10

Which of the following bases cannot deprotonate acetylene? You are given the pKa values of the conjugate acids in parentheses. $\mathrm { CH } _ { 3 } \mathrm { NH } ^ { - } \left( \mathrm { p } K _ { a } = 40 \right) \quad \mathrm { CO } _ { 3 } ^ { 2 - } \left( \mathrm { p } K _ { a } = 10.2 \right) \quad \mathrm { CH } _ { 2 } = \mathrm { CH } ^ { - } \left( \mathrm { p } K _ { a } = 44 \right) \quad \left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm { CO } ^ { - } \left( \mathrm { p } K _ { a } = 18 \right)$
I$\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad$II$\quad\quad\quad\quad\quad\quad\quad\quad\quad$III$\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad$IV

Accepted Answer

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

Question 11

Give the IUPAC name for the following compound.

Accepted Answer

A)  4-Methyl-4-penten-1-yne 
B)  2-Methyl-2-hexen-5-yne 
C)  5-Methyl-4-hexen-1-yne 
D)  2-Methyl-2-penten-4-yne 
A)  4-Methyl-4-penten-1-yne 
B)  2-Methyl-2-hexen-5-yne 
C)  5-Methyl-4-hexen-1-yne 
D)  2-Methyl-2-penten-4-yne

Question 12

Which of the indicated hydrogen in the following compounds is the most acidic?

Accepted Answer

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

Question 13

Rank the following compounds in order of decreasing basicity, putting the most basic first.

Accepted Answer

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

Question 14

Which of the following about the physical properties of alkynes is not true?

Accepted Answer

A)  Alkynes have low melting and boiling points. 
B)  Melting and boiling points increase as the number of carbons increases. 
C)  Alkynes are soluble in organic solvents. 
D)  Alkynes are soluble in water. 
A)  Alkynes have low melting and boiling points. 
B)  Melting and boiling points increase as the number of carbons increases. 
C)  Alkynes are soluble in organic solvents. 
D)  Alkynes are soluble in water.

Question 15

Which of the following statements about the reactions of alkynes is not true?

Accepted Answer

A)  Alkynes contain easily broken F1F1F1S1F1F1F10 bonds. 
B)  Alkynes undergo addition reactions. 
C)  When alkynes undergo two sequential addition reactions, four new F1F1F1S1F1F1F10 bonds are formed. 
D)  When alkynes undergo two sequential addition reactions, two new F1F1F1S1F1F1F10 bonds and a F1F1F1S1F1F1F10 bond are formed. 
A)  Alkynes contain easily broken F1F1F1S1F1F1F10 bonds. 
B)  Alkynes undergo addition reactions. 
C)  When alkynes undergo two sequential addition reactions, four new F1F1F1S1F1F1F10 bonds are formed. 
D)  When alkynes undergo two sequential addition reactions, two new F1F1F1S1F1F1F10 bonds and a F1F1F1S1F1F1F10 bond are formed.

Question 16

Which of the following explains why 1-pentyne has a slightly higher boiling point than 1-pentene?

Accepted Answer

A)  1-Pentyne has more carbons than 1-pentene. 
B)  1-Pentyne has more carbons per hydrogen than 1-pentene. 
C)  1-Pentyne is linear while 1-pentene is trigonal planar. 
D)  The C-C triple bond in 1-pentyne is more polar than the C-C double bond in 1-pentene. 
A)  1-Pentyne has more carbons than 1-pentene. 
B)  1-Pentyne has more carbons per hydrogen than 1-pentene. 
C)  1-Pentyne is linear while 1-pentene is trigonal planar. 
D)  The C-C triple bond in 1-pentyne is more polar than the C-C double bond in 1-pentene.

Question 17

What is the starting material in the following reaction?

Accepted Answer

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

Question 18

Which of the following compounds can be an enol tautomer of 1,3-cyclohexandione?

Accepted Answer

A)  Only I and II 
B)  Only I and III 
C)  Only II and III 
D)  I, II, III 
A)  Only I and II 
B)  Only I and III 
C)  Only II and III 
D)  I, II, III

Question 19

What is the major organic product of the following reaction?

Accepted Answer

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

Question 20

What is the product of the following reaction?

Accepted Answer

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

Exam 11: Alkynes

Give the IUPAC name for the following compound.

Give the IUPAC name for the following compound.

What is the major organic product of the following reaction?

Which of the following represents a keto-enol tautomeric pair?

What is (are) the major organic product(s) of the following reaction?

What is (are) the product(s) of the following reaction?

What is the product of the following reaction?

What is the major organic product of the following reaction?

What is the reagent required to accomplish the following transformation?

Give the IUPAC name for the following compound.

Which of the indicated hydrogen in the following compounds is the most acidic?

Rank the following compounds in order of decreasing basicity, putting the most basic first.

Which of the following about the physical properties of alkynes is not true?

Which of the following statements about the reactions of alkynes is not true?

Which of the following explains why 1-pentyne has a slightly higher boiling point than 1-pentene?

What is the starting material in the following reaction?

Which of the following compounds can be an enol tautomer of 1,3-cyclohexandione?

What is the major organic product of the following reaction?

What is the product of the following reaction?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols, Ethers and Epoxides

Alkenes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Lipids

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