Question 1

Complete the reaction by giving the structure of the organic product.

Accepted Answer

The answer of Complete the reaction by giving the structure...

Question 2

This carbocation undergoes rearrangement. Give the structure of the rearranged carbocation and, on the structure given, the curved-arrow notation for the rearrangement.

Accepted Answer

The answer of This carbocation undergoes rearrangement. Give the structure...

Question 3

Give the structure of the HBr addition product.

Accepted Answer

The Br goes to the more branched carbon and the H to the less branched carbon.

Question 4

Complete the reaction by giving the products. Show all unshared electron pairs and formal charges.

Accepted Answer

The answer of Complete the reaction by giving the products....

Question 5

Consider this reaction. Draw a curved-arrow mechanism for the reaction. Notice that concentrated acid is present as a catalyst. (You can abbreviate the catalyst as H-A in your mechanism.) This mechanism should be a series of acid-base steps.

Accepted Answer

The curved-arrow mechanism is as follows

Question 6

Complete the reaction by giving the major organic product(s).

Accepted Answer

The answer of Complete the reaction by giving the major...

Question 7

Complete the reaction by giving the major organic product(s).

Accepted Answer

The answer of Complete the reaction by giving the major...

Question 8

Select the true statements that apply to a hydrocarbon, compound X, with the molecular formula C10H14. For purposes of the first two statements, a benzene ring has this skeletal structure:

Accepted Answer

A)  Compound X could contain a benzene ring. 
B)  Compound X must contain a benzene ring. 
C)  Compound X has an unsaturation number of 8. 
D)  Compound X has an unsaturation number of 4. 
E)  Compound X could contain three double bonds and one triple bond. 
A)  Compound X could contain a benzene ring. 
B)  Compound X must contain a benzene ring. 
C)  Compound X has an unsaturation number of 8. 
D)  Compound X has an unsaturation number of 4. 
E)  Compound X could contain three double bonds and one triple bond.

Question 9

Which of these alkenes has the smallest (or more negative) heat of formation?

Accepted Answer

A)  Compound A 
B)  Compound B 
C)  Compound C 
D)  Compound D 
E)  Compound E 
A)  Compound A 
B)  Compound B 
C)  Compound C 
D)  Compound D 
E)  Compound E

Question 10

In this pair of compounds, identify the more stable one (as measured by heats of formation).
a.

b.

Accepted Answer

A)  Compound a 
B)  Compound b 
A)  Compound a 
B)  Compound b

Question 11

Complete the reactions by giving the major organic product.

Accepted Answer

The answer of Complete the reactions by giving the major...

Question 12

A multistep reaction A ⇌ B ⇌ C ⇌ D has the free energy-reaction coordinate diagram shown below. Which step of the reaction is rate-limiting in the forward direction?

Accepted Answer

A)  the reaction of A to B 
B)  the reaction of B to C 
C)  the reaction of C to D 
A)  the reaction of A to B 
B)  the reaction of B to C 
C)  the reaction of C to D

Question 13

Provide an IUPAC name for the following compound.

Accepted Answer

2,5-dimeth

Question 14

Name this compound (including stereochemical configuration where appropriate).

Accepted Answer

(E)-3,4-dimethyl-3-h

Question 15

Consider this molecule:
  Which bond is an sp2-sp3 F1F1F1S1F1F1F10 bond?

Accepted Answer

A)  bond (a) 
B)  bond (b) 
C)  bond (c) 
D)  bond (d) 
E)  bond (e) 
A)  bond (a) 
B)  bond (b) 
C)  bond (c) 
D)  bond (d) 
E)  bond (e)

Question 16

14. In each pair, identify the more stable one (as measured by heats of formation).
-2:
a.

b.
  The more stable compound is ________________.

Accepted Answer

A)  Compound a 
B)  Compound b 
A)  Compound a 
B)  Compound b

Question 17

Name the following compound and include the E or Z designation in the name.

Accepted Answer

(E)-2-meth

Question 18

Provide an IUPAC name for the compound.

Accepted Answer

6-ethyl-5-

Question 19

Consider the reaction free-energy diagram for two reactions that convert reactants (R) into products (P) and select the two correct statements.

Accepted Answer

A)  Reaction 1 is faster because it occurs in one step. 
B)  Reaction 2 is faster than reaction 1. 
C)  Both reactions occur at the same rate at a given concentration of R. 
D)  X is a transition state of reaction 2. 
E)  The rate-limiting step of reaction 2 is R ⇌ X.f. 
The rate-limiting step of reaction 2 is X ⇌ P.g. 
X must be a carbocation. 
A)  Reaction 1 is faster because it occurs in one step. 
B)  Reaction 2 is faster than reaction 1. 
C)  Both reactions occur at the same rate at a given concentration of R. 
D)  X is a transition state of reaction 2. 
E)  The rate-limiting step of reaction 2 is R ⇌ X.f. 
The rate-limiting step of reaction 2 is X ⇌ P.g. 
X must be a carbocation.

Question 20

Give the IUPAC name, including stereochemistry, of the compound:

Accepted Answer

5-tert-but

Exam 4: Introduction to Alkenes and Alkynes

Complete the reaction by giving the structure of the organic product.

This carbocation undergoes rearrangement. Give the structure of the rearranged carbocation and, on the structure given, the curved-arrow notation for the rearrangement.

Give the structure of the HBr addition product.

Complete the reaction by giving the products. Show all unshared electron pairs and formal charges.

Consider this reaction. Draw a curved-arrow mechanism for the reaction. Notice that concentrated acid is present as a catalyst. (You can abbreviate the catalyst as H-A in your mechanism.) This mechanism should be a series of acid-base steps.

Complete the reaction by giving the major organic product(s).

Complete the reaction by giving the major organic product(s).

Select the true statements that apply to a hydrocarbon, compound X, with the molecular formula C10H14. For purposes of the first two statements, a benzene ring has this skeletal structure:

Which of these alkenes has the smallest (or more negative) heat of formation?

In this pair of compounds, identify the more stable one (as measured by heats of formation). a. b.

Complete the reactions by giving the major organic product.

A multistep reaction A ⇌ B ⇌ C ⇌ D has the free energy-reaction coordinate diagram shown below. Which step of the reaction is rate-limiting in the forward direction?

Provide an IUPAC name for the following compound.

Name this compound (including stereochemical configuration where appropriate).

Consider this molecule: Which bond is an sp2-sp3  bond?

14. In each pair, identify the more stable one (as measured by heats of formation). -2: a. b. The more stable compound is ________________.

Name the following compound and include the E or Z designation in the name.

Provide an IUPAC name for the compound.

Consider the reaction free-energy diagram for two reactions that convert reactants (R) into products (P) and select the two correct statements.

Give the IUPAC name, including stereochemistry, of the compound:

Chemical Bonding and Chemical Structure

Alkanes and Organic Nomenclature

The Curved-Arrow Notation, Resonance, Acids and Bases, and Chemical Equilibrium

Addition Reactions of Alkenes and Alkynes

Principles of Stereochemistry

Cyclic Compounds and Reaction Stereochemistry

Nomenclature and Noncovalent Intermolecular Interactions

The Chemistry of Alkyl Halides

Free-Radical Reactions, Main-Group Organometallic Compounds, and Carbenes

The Chemistry of Alcohols and Thiols

The Chemistry of Ethers, Epoxides, Glycols, and Sulfides

Introduction to Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Dienes and Aromaticity

The Chemistry of Benzene and Its Derivatives

Allylic and Benzylic Reactivity

The Chemistry of Aryl Halides, Vinylic Halides, and Phenols

The Chemistry of Aldehydes and Ketones

The Chemistry of Carboxylic Acids

The Chemistry of Carboxylic Acid Derivatives

The Chemistry of Enolate Ions, Enols, and Α,β-Unsaturated Carbonyl Compounds

The Chemistry of Amines

Carbohydrates

The Chemistry of Thioesters, Phosphate Esters, and Phosphate Anhydrides

The Chemistry of the Aromatic Heterocycles and Nucleic Acids

Amino Acids, Peptides, and Proteins

Pericyclic Reactions

Filters

Select the true statements that apply to a hydrocarbon, compound X, with the molecular formula C₁₀H₁₄. For purposes of the first two statements, a benzene ring has this skeletal structure:

Consider this molecule: Which bond is an sp²-sp³  bond?