Organic Chemistry Module 4 Problem Set – 2026/2027, Exams of Nursing

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Module 4 Problem Set

Due No due date Points 10 Questions 13 Time Limit None

Attempt History

Attempt Time Score LATEST Attempt 1 16,103 minutes 10 out of 10

Score for this quiz: 10 out of 10

This attempt took 16,103 minutes.

Question 1^0 / 0^ pts

Your Answer:

Explain the difference between alkyl and aryl halides.

Alkyl: Alkyl halides are aliphatic hydrocarbons that possess one or more halogen atom substituents. Aryl: Aryl halides are aromatic hydrocarbons (benzene rings) with one or more halogen atoms attached to the ring.

Answer: Alkyl halides are aliphatic hydrocarbons that possess one or more halogen atom substituents. Aryl halides are aromatic hydrocarbons (benzene rings) with one or more halogen atoms attached to the ring.

Question 2 0 / 0 pts

On a piece of paper, write a structure corresponding to each of the following and then generate the IUPAC name for each.

a. A primary alkyl chloride with MF C 3 H 7 Cl b. A secondary alkyl iodide with MF C 4 H 9 I

c. A tertiary alkyl bromide with MF C 5 H 11 Br

Your Answer: A. 1-chloropropane B. 2-iodobutane C. 2-bromo-2-methylbutane

Question 3 0 / 0 pts

Question 4 0 / 0 pts

Correct!Correct! A. (^) trans-1-chloro-2-methy

Correct!Correct! B. (^) 4-bromo-1,2-dichlorohe

Correct!Correct! C. (^) 2-fluoro-3-methylbutan

Correct!Correct! D. (^) 1 ,3-dichlorobenzene

Correct!Correct! E. (^) 2-iodo-2-methyloctane

Classify each alkyl halide as primary, secondary, or tertiary:

Question 5 0 / 0 pts

Your Answer: A. secondary B. tertiary C. secondary D. primary

Answer: A. Secondary B. Tertiary C. Secondary D. Primary

Explain why nucleophiles attack the carbon that bears the halogen atom during a nucleophilic substitution reaction of an alkyl halide.

Your Answer:

The oxygen molecule has a + charge, which the nucleophiles love.

Question 7 0 / 0 pts

Answer: The polarization of the carbon-halogen bond in an alkyl halide makes the carbon electron-deficient and, as a result, gives it a slight positive charge (as well as a slight negative charge on the halogen correspondingly). The nucleophile (positive- charge lover) is thus attracted to the electron-deficient carbon.

In each of the following reactions, identify the nucleophile , substrate , and leaving group.

Nucleophile Substrate Leaving Group

a) 1.__________ 2.__________ 3._________

b) 4.__________ 5.__________ 6.__________

Your Answer:

1. 1-bromobutane
2. Br
3. Hydroxide ion
4. 2-iodo-2-methylproane
5. I
6. Cyanide

Question 10 0 / 0 pts

Your Answer:

Classify each solvent listed as being protic or aprotic.

i. Water (H O) ii. Methanol (CH OH) iii. Acetone (CH C=OCH ) iv. DMSO (dimethylsulfoxide) (CH SOCH )

2 3 3 3 3 3

i. aprotic

ii. protic

iii. aprotic

iv. protic

Answer: i. Protic ii. Protic iii. Aprotic iv. Aprotic

Label each of the following characteristics as being associated with either the SN1 or SN2 substitution mechanism type:

Characteristic SN1 or SN2?

The reaction happens in a series of steps. 1._______

The nucleophile “attacks” from the backside of the CL bond. 2._______

There is no inversion of tetrahedral geometry at the leaving group carbon. 3._______

Analogous to a gust of wind turning an umbrella inside out, the orientation of the groups that remain attached to the leaving group carbon “flip” (or invert) when the substitution occurs. (Inversion)

4._______

The reaction occurs in a single step. 5._______

The leaving group leaves first. 6._______

Typically associated with bulky substrates (tertiary) 7._______

Typically associated with non-bulky substrates (methyl/primary)

8._______

1. Sn
2. Sn
3. Sn
4. Sn
5. Sn
6. Sn
7. Sn
8. Sn

Answer:

Characteristic S 1 or S 2?

The reaction happens in a series of steps. 1. S 1

The nucleophile “attacks” from the backside of the C-L bond.

2. S 2

There is no inversion of tetrahedral geometry at the leaving group carbon.

3. S 1

Analogous to a gust of wind turning an umbrella inside out, the orientation of the groups that remain attached to the leaving group carbon “flip” (or invert) when the substitution occurs. ( Inversion)

4. S 2

The reaction occurs in a single step. 5. S 2

The leaving group leaves first. 6. S 1

Typically associated with bulky substrates ( tertiary )

7. S 1

Typically associated with non-bulky substrates (methyl/primary )

8. S 2

N N

N N N N N N N N

Question 11 0 / 0 pts

How many different alkene products could be formed if elimination occurred on each of the following alkyl halide substrates? Do not take E/Z stereoisomers into account. Only consider the different constitutional isomers that can form.

Your Answer:

Two

B. A secondary alkyl halide (R 2 CHX) – while 4._____mechanistic pathways

are possible, typically these substrates will react by both ______ _5.______ (when weak bases are used) and 6. (when strong bases are used) pathways to give a mixture of substitution and elimination products.

C. A tertiary alkyl halide (R 3 X) will react by a(n) ______ 7. ________ pathway when a strong and/or bulky base is used as the nucleophile. When a weak nucleophile is used (or under acidic conditions), a mixture of substitution and elimination products will form by

8. No 9. pathway is available for tertiary substrates.

Your Answer:

1. SN 2
2. elimination
3. E
4. four
5. product
6. E
7. E
8. SN 1
9. SN

Answer:

A. A primary alkyl halide (RCH 2 X) will react by an 1. SN 2 pathway if a good nucleophile (examples include I-, Br-, RS-, NH 3 , or CN-) is used. There will be increasing amounts of 2. elimination product from an 3. E2 pathway as the basicity of the nucleophile increases (examples include HO-, RO-). No SN1 or E1 pathways are possible for primary substrates. B. A secondary alkyl halide (R 2 CHX) – while 4. all four mechanistic pathways are possible, typically these substrates will react by both 5. SN 2 (when weak bases are used) and 6. E2 (when strong bases are used) pathways to give a mixture of substitution and elimination products.