Question 1

What is the IUPAC name for di-sec-butylacetylene?

Accepted Answer

A)  2-ethyl-5-methyl-3-heptyne 
B)  2,7-dimethyl-4-octyne 
C)  3,6-dimethyl-4-octyne 
D)  2,5-diethyl-3-hexyne 
E)  2,2,5,5-tetramethyl-3-hexyne 
A)  2-ethyl-5-methyl-3-heptyne 
B)  2,7-dimethyl-4-octyne 
C)  3,6-dimethyl-4-octyne 
D)  2,5-diethyl-3-hexyne 
E)  2,2,5,5-tetramethyl-3-hexyne

Question 2

Which of the following is the structure for 2,5,5?trimethylhept?3?yne?

Accepted Answer

A)  CH3CH2CH(CH3)C≡CCH2CH(CH3)2 
B)  CH3CH2C(CH3)2C≡CCH(CH3)2 
C)  (CH3CH2)2C(CH3)C≡CCH2CH3 
D)  CH3CH2C(CH3)2C≡CC(CH3)3 
E)  CH3CH2CH2CH(CH3)C≡CC(CH3)3 
A)  CH3CH2CH(CH3)C≡CCH2CH(CH3)2 
B)  CH3CH2C(CH3)2C≡CCH(CH3)2 
C)  (CH3CH2)2C(CH3)C≡CCH2CH3 
D)  CH3CH2C(CH3)2C≡CC(CH3)3 
E)  CH3CH2CH2CH(CH3)C≡CC(CH3)3

Question 3

Which alkyne would produce the products below upon ozonolysis?

Accepted Answer

A)  HC≡CC≡CCH2C≡CH 
B)  HC≡CCH2CH2CH2C≡CH 
C)  CH3C≡CCH2C≡CCH3 
D)  HC≡CCH2CH2C≡CCH3 
E)  CH3C≡CC≡CC≡CH 
A)  HC≡CC≡CCH2C≡CH 
B)  HC≡CCH2CH2CH2C≡CH 
C)  CH3C≡CCH2C≡CCH3 
D)  HC≡CCH2CH2C≡CCH3 
E)  CH3C≡CC≡CC≡CH

Question 4

Which of the following alkynes would give a single product under hydroboration-oxidation conditions?

Accepted Answer

A)  1-hexyne 
B)  2-hexyne 
C)  3-hexyne 
D)  A and B would each give a single product 
E)  A and C would each give a single product 
A)  1-hexyne 
B)  2-hexyne 
C)  3-hexyne 
D)  A and B would each give a single product 
E)  A and C would each give a single product

Question 5

Reaction of (3E,5Z)-3-methylhepta-3,5-dien-1-yne with H2 and Pd/C will produce which of the compounds below?

Accepted Answer

A)  1-sec-butylbutane 
B)  2-butylbutane2 
C)  3-methylheptane 
D)  3-methyl-1-heptyne 
E)  (3E,5Z)-3-methyl-1,3,5-heptatriene 
A)  1-sec-butylbutane 
B)  2-butylbutane2 
C)  3-methylheptane 
D)  3-methyl-1-heptyne 
E)  (3E,5Z)-3-methyl-1,3,5-heptatriene

Question 6

Provide the IUPAC name for the following compound.

Accepted Answer

(4R,5S)-4-bromo-5-ch

Question 7

Provide the IUPAC name for Cl3CCH2CH2CH2C≡CH.

Accepted Answer

A)  6,6,6-trichloro-1-hexyne 
B)  1,1,1-trichloro-5-hexyne 
C)  5,5,5-trichloro-1-pentyne 
D)  1-heptyne 
E)  trichlorobutylacetylene 
A)  6,6,6-trichloro-1-hexyne 
B)  1,1,1-trichloro-5-hexyne 
C)  5,5,5-trichloro-1-pentyne 
D)  1-heptyne 
E)  trichlorobutylacetylene

Question 8

What is the IUPAC name for the molecule shown below?

Accepted Answer

A)  4-ethyl-2-pentyne 
B)  2-ethyl-3-pentyne 
C)  3-methyl-4-hexyne 
D)  4-methyl-2-hexyne 
E)  sec-Butylpropyne 
A)  4-ethyl-2-pentyne 
B)  2-ethyl-3-pentyne 
C)  3-methyl-4-hexyne 
D)  4-methyl-2-hexyne 
E)  sec-Butylpropyne

Question 9

Select the reagent(s) expected to accomplish the reaction shown below.

Accepted Answer

A)  H2, Pd 
B)  H2, Lindlar's catalyst 
C)  Na, NH3(l) 
D)  A or B 
E)  B or C 
A)  H2, Pd 
B)  H2, Lindlar's catalyst 
C)  Na, NH3(l) 
D)  A or B 
E)  B or C

Question 10

Which of the following statements best describes the general reactivity of alkynes?

Accepted Answer

A)  An alkyne reacts as a nucleophile and is therefore electron rich. 
B)  An alkyne reacts as a nucleophile and is therefore electron poor. 
C)  Alkynes fail to undergo electrophilic addition reactions, unlike alkenes. 
D)  An alkyne reacts as an electrophile and is therefore electron rich. 
E)  An alkyne reacts as an electrophile and is therefore electron poor. 
A)  An alkyne reacts as a nucleophile and is therefore electron rich. 
B)  An alkyne reacts as a nucleophile and is therefore electron poor. 
C)  Alkynes fail to undergo electrophilic addition reactions, unlike alkenes. 
D)  An alkyne reacts as an electrophile and is therefore electron rich. 
E)  An alkyne reacts as an electrophile and is therefore electron poor.

Question 11

For the reaction below, how many different organic products would be expected?

Accepted Answer

A)  one 
B)  two 
C)  three 
D)  four 
E)  five 
A)  one 
B)  two 
C)  three 
D)  four 
E)  five

Question 12

What is the expected major product of the reaction sequence shown below?

Accepted Answer

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

Question 13

Select the alkyne listed below that, upon treatment with ozone followed by water, would not produce carbon dioxide and a carboxylic acid as the final products?

Accepted Answer

A)  ethyne 
B)  propyne 
C)  1-butyne 
D)  1-pentyne 
E)  1-hexyne 
A)  ethyne 
B)  propyne 
C)  1-butyne 
D)  1-pentyne 
E)  1-hexyne

Question 14

Which sequence of reagents would be expected to accomplish the synthesis of 1-butyne shown below?

Accepted Answer

A)  1. H2O/H2SO4, HgSO4 cat.; 2. H2, Pt 
B)  1. HBr; 2. H2, Pt; 3. NaOH 
C)  1. H2, Lindlar catalyst; 2. BH3•THF; 3. H2O2, NaOH 
D)  1. HBr, peroxides; 2. NaOH; 3. H2, Pt 
E)  1. O3 2. H2O 
A)  1. H2O/H2SO4, HgSO4 cat.; 2. H2, Pt 
B)  1. HBr; 2. H2, Pt; 3. NaOH 
C)  1. H2, Lindlar catalyst; 2. BH3•THF; 3. H2O2, NaOH 
D)  1. HBr, peroxides; 2. NaOH; 3. H2, Pt 
E)  1. O3 2. H2O

Question 15

Which sequence of reactions is expected to produce the product below as the final, and major, organic product?

Accepted Answer

A)  1. Br2, CCl4 2. H2, Lindlar's cat. 
B)  1. H2, Lindlar's cat.; 2. Br2 
C)  1. Br2, CCl4 2. Na, NH3(l) 
D)  1. Na, NH3(l); 2. Br2 
E)  1. Br2, CCl4 2. H2, Pt 
A)  1. Br2, CCl4 2. H2, Lindlar's cat. 
B)  1. H2, Lindlar's cat.; 2. Br2 
C)  1. Br2, CCl4 2. Na, NH3(l) 
D)  1. Na, NH3(l); 2. Br2 
E)  1. Br2, CCl4 2. H2, Pt

Question 16

For the reaction shown, select the expected major organic product.

Accepted Answer

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

Question 17

Which sequence of reactions is expected to produce the product below as the final, and major, organic product?

Accepted Answer

A)  1. H2, Lindlar's cat.; 2. OsO4; 3. NaHSO3/H2O 
B)  1. H2, Pt; 2. OsO4; 3. NaHSO3/H2O 
C)  1. OsO4; 2. NaHSO3/H2O; 3. H2, Lindlar's cat. 
D)  1. Na, NH3(l); 2. OsO4; 3. NaHSO3/H2O 
E)  1. OsO4; 2.NaHSO3/H2O; 3. Na, NH3(l) 
A)  1. H2, Lindlar's cat.; 2. OsO4; 3. NaHSO3/H2O 
B)  1. H2, Pt; 2. OsO4; 3. NaHSO3/H2O 
C)  1. OsO4; 2. NaHSO3/H2O; 3. H2, Lindlar's cat. 
D)  1. Na, NH3(l); 2. OsO4; 3. NaHSO3/H2O 
E)  1. OsO4; 2.NaHSO3/H2O; 3. Na, NH3(l)

Question 18

Which of the following is a structure for octa-3,6-dien-1-yne?

Accepted Answer

A)  HC≡CCH=CHCH=CHCH2CH3 
B)  CH3CH=CHCH2C≡CC≡CH 
C)  CH3CH=CHCH2CH=CHC≡CH 
D)  CH3C≡CCH=CHCH=CHCH3 
E)  H2C=CHC≡CCH2CH=CHCH3 
A)  HC≡CCH=CHCH=CHCH2CH3 
B)  CH3CH=CHCH2C≡CC≡CH 
C)  CH3CH=CHCH2CH=CHC≡CH 
D)  CH3C≡CCH=CHCH=CHCH3 
E)  H2C=CHC≡CCH2CH=CHCH3

Question 19

What is the IUPAC name for the molecule shown below?

Accepted Answer

A)  2,2,3-trimethyl-4-hexyne 
B)  4-tert-butyl-2-pentyne 
C)  4,5,5-trimethyl-2-hexyne 
D)  4,5,5,5-tetramethyl-2-pentyne 
E)  2,2-dimethyl-3-(1-propynyl)butane 
A)  2,2,3-trimethyl-4-hexyne 
B)  4-tert-butyl-2-pentyne 
C)  4,5,5-trimethyl-2-hexyne 
D)  4,5,5,5-tetramethyl-2-pentyne 
E)  2,2-dimethyl-3-(1-propynyl)butane

Question 20

Identify the final 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 9: Alkynes

What is the IUPAC name for di-sec-butylacetylene?

Which of the following is the structure for 2,5,5?trimethylhept?3?yne?

Which alkyne would produce the products below upon ozonolysis?

Which of the following alkynes would give a single product under hydroboration-oxidation conditions?

Reaction of (3E,5Z)-3-methylhepta-3,5-dien-1-yne with H2 and Pd/C will produce which of the compounds below?

Provide the IUPAC name for the following compound.

Provide the IUPAC name for Cl3CCH2CH2CH2C≡CH.

What is the IUPAC name for the molecule shown below?

Select the reagent(s) expected to accomplish the reaction shown below.

Which of the following statements best describes the general reactivity of alkynes?

For the reaction below, how many different organic products would be expected?

What is the expected major product of the reaction sequence shown below?

Select the alkyne listed below that, upon treatment with ozone followed by water, would not produce carbon dioxide and a carboxylic acid as the final products?

Which sequence of reagents would be expected to accomplish the synthesis of 1-butyne shown below?

Which sequence of reactions is expected to produce the product below as the final, and major, organic product?

For the reaction shown, select the expected major organic product.

Which sequence of reactions is expected to produce the product below as the final, and major, organic product?

Which of the following is a structure for octa-3,6-dien-1-yne?

What is the IUPAC name for the molecule shown below?

Identify the final 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

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

Amines

Introduction to Organometallic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Reaction of (3E,5Z)-3-methylhepta-3,5-dien-1-yne with H₂and Pd/C will produce which of the compounds below?

Provide the IUPAC name for Cl₃CCH₂CH₂CH₂C≡CH.