Question 1

What are the expected major products of the reaction sequence shown below?

Accepted Answer

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

Question 2

What is the IUPAC name for the molecule shown below?

Accepted Answer

A)  1,1,1-trichloro-4-hexyne 
B)  4,4,4-trichloro-1-butyne 
C)  1,1,1-trichloro-2-butyne 
D)  5,5,5-trichloro-2-pentyne 
E)  6,6,6-trichloro-2-hexyne 
A)  1,1,1-trichloro-4-hexyne 
B)  4,4,4-trichloro-1-butyne 
C)  1,1,1-trichloro-2-butyne 
D)  5,5,5-trichloro-2-pentyne 
E)  6,6,6-trichloro-2-hexyne

Question 3

Provide the IUPAC name for the following compound:

Accepted Answer

(3E,5S)-5-fluoro-2-m

Question 4

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

Accepted Answer

@#IMG-DLM&_TB4454_00

Question 5

Identify the product of the reaction of an alkyne with sodium and ammonia.

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

Question 6

Predict the major organic products of the reaction below.

Accepted Answer

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

Question 7

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 8

Consider the list of alkyne addition reactions below, and select all those that involve an enol intermediate.

Accepted Answer

A)  Hydroboration/oxidation 
B)  HgSO4 catalyzed hydration in dilute H2SO4 
C)  Hydrohalogenation 
D)  Both A and B 
E)  Both A and C 
A)  Hydroboration/oxidation 
B)  HgSO4 catalyzed hydration in dilute H2SO4 
C)  Hydrohalogenation 
D)  Both A and B 
E)  Both A and C

Question 9

Rank the following carbanions in order of increasing pKa.

Accepted Answer

A)  I < II < III 
B)  II < III < I 
C)  III < II < I 
D)  III < I < II 
E)  II < I < III 
A)  I < II < III 
B)  II < III < I 
C)  III < II < I 
D)  III < I < II 
E)  II < I < III

Question 10

Why would the following synthetic route shown below be unsuccessful?

Accepted Answer

The alkynide anion formed by r

Question 11

What is the IUPAC name for diisobutylacetylene?

Accepted Answer

A)  diisopropylbutyne 
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)  diisopropylbutyne 
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 12

Which of the bases below would result in the most complete deprotonation of the alkyne, shown in the reaction below?

Accepted Answer

A)  NaOCH2CH3 (sodium ethoxide) 
B)  t-BuONa (sodium tert-butoxide) 
C)  NaH (sodium hydride) 
D)  NaHCO3 (sodium bicarbonate) 
E)  NaOH (sodium hydroxide) 
A)  NaOCH2CH3 (sodium ethoxide) 
B)  t-BuONa (sodium tert-butoxide) 
C)  NaH (sodium hydride) 
D)  NaHCO3 (sodium bicarbonate) 
E)  NaOH (sodium hydroxide)

Question 13

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

Accepted Answer

A)  H2, Ni 
B)  H2, Ni2B 
C)  H2, Lindlar's catalyst 
D)  A and B 
E)  B and C 
A)  H2, Ni 
B)  H2, Ni2B 
C)  H2, Lindlar's catalyst 
D)  A and B 
E)  B and C

Question 14

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 15

Compound X, a geminal dihalide, is exposed to excess strong base (excess NaNH2 then H2O) to produce an alkyne (compound Y). Alkyne Y is a terminal alkyne, has a molecular formula of C5H8, and has exactly 4 distinct resonances in the (proton-decoupled) 13C NMR spectrum. What are the two possible structures for compound X?

Accepted Answer

Question 16

What is the expected major organic product from the treatment of 4-methyl-2-pentyne with excess hydrogen in the presence of a platinum catalyst?

Accepted Answer

The answer of What is the expected major organic product...

Question 17

How many moles of hydrogen are required for the complete reduction of 1 mole of (3E,5Z)-3-methylhepta-3,5-dien-1-yne?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
E)  5 
A)  1 
B)  2 
C)  3 
D)  4 
E)  5

Question 18

What is the IUPAC name for the molecule shown below?

Accepted Answer

A)  4,4-dimethyl-2-pentyne 
B)  2,2-dimethyl-4-heptyne 
C)  1-tert-butyl-3-heptyne 
D)  6,6-dimethyl-3-heptyne 
E)  6,6,6-trimethyl-3-hexyne 
A)  4,4-dimethyl-2-pentyne 
B)  2,2-dimethyl-4-heptyne 
C)  1-tert-butyl-3-heptyne 
D)  6,6-dimethyl-3-heptyne 
E)  6,6,6-trimethyl-3-hexyne

Question 19

For the reaction shown below, what is the IUPAC name of the expected product?

Accepted Answer

A)  2-methylhexane 
B)  (Z)-2-methyl-4-hexene 
C)  (
E) -2-methyl-4-hexene 
D)  (Z)-5-methyl-2-hexene 
E)  (
E) -5-methyl-2-hexene 
A)  2-methylhexane 
B)  (Z)-2-methyl-4-hexene 
C)  (
E) -2-methyl-4-hexene 
D)  (Z)-5-methyl-2-hexene 
E)  (
E) -5-methyl-2-hexene

Question 20

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

Accepted Answer

A)  1. Na, NH3(l); 2. OsO4; 3. NaHSO3/H2O 
B)  1. H2, Lindlar's cat.; 2. MCPBA; 3. H3O+ 
C)  1. H2, Ni2B (P-2); 2. KMnO4, NaOH (cold) 
D)  Both A and B 
E)  Both A and C 
A)  1. Na, NH3(l); 2. OsO4; 3. NaHSO3/H2O 
B)  1. H2, Lindlar's cat.; 2. MCPBA; 3. H3O+ 
C)  1. H2, Ni2B (P-2); 2. KMnO4, NaOH (cold) 
D)  Both A and B 
E)  Both A and C

Exam 9: Alkynes

What are the expected major products of the reaction sequence shown below?

What is the IUPAC name for the molecule shown below?

Provide the IUPAC name for the following compound:

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

Identify the product of the reaction of an alkyne with sodium and ammonia.

Predict the major organic products of the reaction below.

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

Consider the list of alkyne addition reactions below, and select all those that involve an enol intermediate.

Rank the following carbanions in order of increasing pKa.

Why would the following synthetic route shown below be unsuccessful?

What is the IUPAC name for diisobutylacetylene?

Which of the bases below would result in the most complete deprotonation of the alkyne, shown in the reaction below?

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

Identify the best reagent(s) for this reaction.

What is the expected major organic product from the treatment of 4-methyl-2-pentyne with excess hydrogen in the presence of a platinum catalyst?

How many moles of hydrogen are required for the complete reduction of 1 mole of (3E,5Z)-3-methylhepta-3,5-dien-1-yne?

What is the IUPAC name for the molecule shown below?

For the reaction shown below, what is the IUPAC name of the expected product?

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

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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