Question 1

Provide the reagent(s) expected to accomplish the synthesis shown below.

Accepted Answer

H<sub>2</sub>, Pt

Question 2

Identify the product of the reaction of an alkyne with hydrogen and Lindlar's catalyst.

Accepted Answer

A)  cis alkene 
B)  trans alkene 
C)  diene 
D)  alkyne 
E)  alkane 
A)  cis alkene 
B)  trans alkene 
C)  diene 
D)  alkyne 
E)  alkane A

Question 3

The sigma bond of an alkyne is formed from the overlap of which two orbitals?

Accepted Answer

A)  sp3-sp3 
B)  p-p 
C)  sp2-sp2 
D)  s-s 
E)  sp-sp 
A)  sp3-sp3 
B)  p-p 
C)  sp2-sp2 
D)  s-s 
E)  sp-sp E

Question 4

Provide the structure(s) of the expected major organic product from the following reaction.

Accepted Answer

The answer of Provide the structure(s) of the expected major...

Question 5

Draw all of the constitutionally isomeric alkynes with molecular formula C5H8.

Accepted Answer

Question 6

Which reagents shown below would be expected to convert 2-pentyne to (Z)-2-pentene?

Accepted Answer

A)  H2, Pt 
B)  Na, NH3 
C)  H2, Lindlar's catalyst 
D)  excess HCl 
E)  HgSO4, H2O 
A)  H2, Pt 
B)  Na, NH3 
C)  H2, Lindlar's catalyst 
D)  excess HCl 
E)  HgSO4, H2O

Question 7

Give the hybridization for the carbanion in the acetylide ion.

Accepted Answer

A)  sp 
B)  sp2 
C)  sp3 
D)  s2p 
E)  s2p2 
A)  sp 
B)  sp2 
C)  sp3 
D)  s2p 
E)  s2p2

Question 8

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 9

Rank the following acids in order of decreasing acidity.

Accepted Answer

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

Question 10

What are the products of the reaction shown below? CH3OH + CH3C≡C-Na+ → ?

Accepted Answer

A)  CH3C≡CCH3 + Na+OH- 
B)  CH3C≡CH + CH3O-Na+ 
C)  CH3C≡COCH3 + Na+OH- 
D)  CH3OC≡CH + Na+CH3- 
E)  no reaction 
A)  CH3C≡CCH3 + Na+OH- 
B)  CH3C≡CH + CH3O-Na+ 
C)  CH3C≡COCH3 + Na+OH- 
D)  CH3OC≡CH + Na+CH3- 
E)  no reaction

Question 11

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

Question 12

Which of the following is the structure for (2E,4E)-octa-2,4-dien-6-yne?

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 the IUPAC name for CH3CHBrC≡C(CH2)3CH3.

Accepted Answer

2-bromo-3-

Question 14

Which of the following alkynes, upon ozonolysis, would be expected to produce only one major organic product?

Accepted Answer

A)  1-hexyne 
B)  2-hexyne 
C)  3-hexyne 
D)  2-heptyne 
E)  3-heptyne 
A)  1-hexyne 
B)  2-hexyne 
C)  3-hexyne 
D)  2-heptyne 
E)  3-heptyne

Question 15

Draw all constitutional isomers of the molecular formula C6H10 that are internal alkynes.

Accepted Answer

Question 16

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

Question 17

Select the best reagent expected to convert 3-heptyne to cis-3-heptene.

Accepted Answer

A)  NaNH2, NH3 
B)  Na, NH3 
C)  H2, Lindlar's catalyst 
D)  Both A and C 
E)  Both B and C 
A)  NaNH2, NH3 
B)  Na, NH3 
C)  H2, Lindlar's catalyst 
D)  Both A and C 
E)  Both B and C

Question 18

For 2,4-hexadiyne, which of the following describes the orbital overlap of the C3-C4 sigma bond?

Accepted Answer

A)  sp-sp 
B)  sp2-sp2 
C)  sp3-sp3 
D)  p-p 
E)  sp3-sp 
A)  sp-sp 
B)  sp2-sp2 
C)  sp3-sp3 
D)  p-p 
E)  sp3-sp

Question 19

Provide the IUPAC name for the following compound.

Accepted Answer

(S)-2,3,6,6-tetramet

Question 20

Which of the alkyl bromides listed would work as a reagent in step 2 of the reaction sequence shown, with the resulting major product being an internal alkyne?

Accepted Answer

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

Exam 9: Alkynes

Provide the reagent(s) expected to accomplish the synthesis shown below.

Identify the product of the reaction of an alkyne with hydrogen and Lindlar's catalyst.

The sigma bond of an alkyne is formed from the overlap of which two orbitals?

Provide the structure(s) of the expected major organic product from the following reaction.

Draw all of the constitutionally isomeric alkynes with molecular formula C5H8.

Which reagents shown below would be expected to convert 2-pentyne to (Z)-2-pentene?

Give the hybridization for the carbanion in the acetylide ion.

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

Rank the following acids in order of decreasing acidity.

What are the products of the reaction shown below? CH3OH + CH3C≡C-Na+ → ?

Identify the final product for the following reaction.

Which of the following is the structure for (2E,4E)-octa-2,4-dien-6-yne?

Provide the IUPAC name for CH3CHBrC≡C(CH2)3CH3.

Which of the following alkynes, upon ozonolysis, would be expected to produce only one major organic product?

Draw all constitutional isomers of the molecular formula C6H10 that are internal alkynes.

Identify the final product for the following reaction.

Select the best reagent expected to convert 3-heptyne to cis-3-heptene.

For 2,4-hexadiyne, which of the following describes the orbital overlap of the C3-C4 sigma bond?

Provide the IUPAC name for the following compound.

Which of the alkyl bromides listed would work as a reagent in step 2 of the reaction sequence shown, with the resulting major product being an internal alkyne?

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

Draw all of the constitutionally isomeric alkynes with molecular formula C₅H₈.

What are the products of the reaction shown below? CH₃OH + CH₃C≡C^-Na⁺ → ?

Provide the IUPAC name for CH₃CHBrC≡C(CH₂)₃CH₃.

Draw all constitutional isomers of the molecular formula C₆H₁₀ that are internal alkynes.