Question 1

Provide the IUPAC name for the following compound.

Accepted Answer

4,4-dimeth

Question 2

For the reaction shown, which of the compounds listed below would be the expected major, and final, 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 3

A dihalide in which the halogens are attached on the same carbon is called a _______________ dihalide.

Accepted Answer

A)  vicinal 
B)  geminal 
C)  vinylic 
D)  allylic 
E)  cis 
A)  vicinal 
B)  geminal 
C)  vinylic 
D)  allylic 
E)  cis

Question 4

Which of the following methods would be expected to efficiently produce cis-2-butene as the major organic product?

Accepted Answer

A)  CH3CHBrCH2CH3 + (CH3)3COK/(CH3)3COH 
B)  CH3C≡CCH3 + H2, Pt 
C)  CH3C≡CCH3 + H2, Ni2B (P-2) 
D)  CH3C≡CCH3 + Na, NH3(l) 
E)  CH3CHBrCH2CH3 + NaNH2 
A)  CH3CHBrCH2CH3 + (CH3)3COK/(CH3)3COH 
B)  CH3C≡CCH3 + H2, Pt 
C)  CH3C≡CCH3 + H2, Ni2B (P-2) 
D)  CH3C≡CCH3 + Na, NH3(l) 
E)  CH3CHBrCH2CH3 + NaNH2

Question 5

In the reaction between an alkyne and Na metal in liquid ammonia, the role of Na is an a(n) ___________.

Accepted Answer

A)  Brønsted acid 
B)  Brønsted base 
C)  reducing agent 
D)  catalyst 
E)  electrophile 
A)  Brønsted acid 
B)  Brønsted base 
C)  reducing agent 
D)  catalyst 
E)  electrophile

Question 6

Which of the compounds shown below would be the most likely product expected from the reaction scheme shown?

Accepted Answer

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

Question 7

Identify the best reagent(s) for this reaction.

Accepted Answer

A)  H2SO4, HgSO4, H2O 
B)  1. Disiamylborane, 2. HO-, H2O2 
C)  K2Cr2O7, H+ 
D)  NaOCl 
E)  H2, Pd 
A)  H2SO4, HgSO4, H2O 
B)  1. Disiamylborane, 2. HO-, H2O2 
C)  K2Cr2O7, H+ 
D)  NaOCl 
E)  H2, Pd

Question 8

What is the expected major organic product from the treatment of 4-methyl-2-pentyne with hydrogen in the presence of Lindlar's catalyst?

Accepted Answer

(Z)-4-meth

Question 9

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

Accepted Answer

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

Question 10

For the reaction shown below, the expected product will have a stereochemistry of ______.

Accepted Answer

A)  only (S) 
B)  only (R) 
C)  racemic 
D)  meso 
E)  achiral 
A)  only (S) 
B)  only (R) 
C)  racemic 
D)  meso 
E)  achiral

Question 11

Which of the compounds shown below would be the most likely product expected from the reaction scheme shown?

Accepted Answer

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

Question 12

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 13

Draw the line-bond structure for the compound with the IUPAC name 2,5,9-trimethyl-2-decen-7-yne.

Accepted Answer

The answer of Draw the line-bond structure for the compound...

Question 14

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 15

What is the IUPAC name for the molecule shown below?

Accepted Answer

A)  3-bromo-4-acetylenylheptane 
B)  3-(1-bromopropyl)-1-hexyne 
C)  3-bromo-4-propyl-5-hexyne 
D)  4-bromo-3-propyl-1-hexyne 
E)  4-ethynyl-5-bromo-heptane 
A)  3-bromo-4-acetylenylheptane 
B)  3-(1-bromopropyl)-1-hexyne 
C)  3-bromo-4-propyl-5-hexyne 
D)  4-bromo-3-propyl-1-hexyne 
E)  4-ethynyl-5-bromo-heptane

Question 16

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

Accepted Answer

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

Question 17

In a dissolving metal reduction of an alkyne, a postulated intermediate is the trans alkenyl radical, shown below. In which orbital type would the unpaired electron be located?

Accepted Answer

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

Question 18

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 19

What is the hybridization of the carbon atoms numbered 1 and 2 respectively in the following structure?

Accepted Answer

A)  sp3, sp2 
B)  sp2, sp2 
C)  sp, sp 
D)  sp2, sp 
E)  sp, sp2 
A)  sp3, sp2 
B)  sp2, sp2 
C)  sp, sp 
D)  sp2, sp 
E)  sp, sp2

Question 20

For 2-pentyne, which of the following describes the orbital overlap of the C2-C3 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

Exam 9: Alkynes

Provide the IUPAC name for the following compound.

For the reaction shown, which of the compounds listed below would be the expected major, and final, organic product?

A dihalide in which the halogens are attached on the same carbon is called a _______________ dihalide.

Which of the following methods would be expected to efficiently produce cis-2-butene as the major organic product?

In the reaction between an alkyne and Na metal in liquid ammonia, the role of Na is an a(n) ___________.

Which of the compounds shown below would be the most likely product expected from the reaction scheme shown?

Identify the best reagent(s) for this reaction.

What is the expected major organic product from the treatment of 4-methyl-2-pentyne with hydrogen in the presence of Lindlar's catalyst?

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

For the reaction shown below, the expected product will have a stereochemistry of ______.

Which of the compounds shown below would be the most likely product expected from the reaction scheme shown?

Identify the final product for the following reaction.

Draw the line-bond structure for the compound with the IUPAC name 2,5,9-trimethyl-2-decen-7-yne.

Identify the final product for the following reaction.

What is the IUPAC name for the molecule shown below?

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

In a dissolving metal reduction of an alkyne, a postulated intermediate is the trans alkenyl radical, shown below. In which orbital type would the unpaired electron be located?

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

What is the hybridization of the carbon atoms numbered 1 and 2 respectively in the following structure?

For 2-pentyne, which of the following describes the orbital overlap of the C2-C3 sigma bond?

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

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