Solved

Passage A Group of Students Studied the Reactivity of Four Alkyl

Question 120

Multiple Choice

Passage
A group of students studied the reactivity of four alkyl halides (R−X) in two nucleophilic substitution reactions.  Nucleophilic substitution reactions can go through one of two mechanisms.  The SN2 reaction requires substitution of a leaving group with a nucleophile in a single step (Reaction 1) , and the SN1 reaction requires elimination of the leaving group and formation of an intermediate before nucleophilic substitution can occur, resulting in a two-step process (Reaction 2) .R−X + NaI → R−I + NaX↓Reaction 1R−X + AgNO3 → R+ + AgX↓ + HOCH2CH3 → R−OCH2CH3 + HNO3Reaction 2Experiment 1The students performed the SN2 reaction (Reaction 1) by the addition of a few drops of each alkyl halide into a separate test tube containing 1 mL of 15% solution of NaI in acetone at 25°C.  After mixing, they monitored the reaction for the formation of a precipitate (sodium halide salt) .  If no precipitate formed after 5 minutes, they raised the temperature of the reaction to 50°C and again checked for the formation of a precipitate.  Formation of a precipitate indicated the substrate underwent nucleophilic substitution.  The results observed for the Finkelstein reaction are shown in Table 1.Table 1  Results of the SN2 Reaction
Passage A group of students studied the reactivity of four alkyl halides (R−X) in two nucleophilic substitution reactions.  Nucleophilic substitution reactions can go through one of two mechanisms.  The S<sub>N</sub>2 reaction requires substitution of a leaving group with a nucleophile in a single step (Reaction 1) , and the S<sub>N</sub>1 reaction requires elimination of the leaving group and formation of an intermediate before nucleophilic substitution can occur, resulting in a two-step process (Reaction 2) .R−X + NaI → R−I + NaX↓<strong>Reaction 1</strong>R−X + AgNO<sub>3</sub> → R<sup>+</sup> + AgX↓ + HOCH<sub>2</sub>CH<sub>3</sub> → R−OCH<sub>2</sub>CH<sub>3</sub> + HNO<sub>3</sub><strong>Reaction 2</strong>Experiment 1The students performed the S<sub>N</sub>2 reaction (Reaction 1) by the addition of a few drops of each alkyl halide into a separate test tube containing 1 mL of 15% solution of NaI in acetone at 25°C.  After mixing, they monitored the reaction for the formation of a precipitate (sodium halide salt) .  If no precipitate formed after 5 minutes, they raised the temperature of the reaction to 50°C and again checked for the formation of a precipitate.  Formation of a precipitate indicated the substrate underwent nucleophilic substitution.  The results observed for the Finkelstein reaction are shown in Table 1.<strong>Table 1</strong>  Results of the S<sub>N</sub>2 Reaction Experiment 2The students repeated the procedure followed in Experiment 1 except they added a few drops of each alkyl halide into a separate test tube containing 1 mL of 1% solution of AgNO<sub>3</sub> in ethanol at 25°C.  The results observed for this reaction are shown in Table 2.<strong>Table 2</strong>  Results of the S<sub>N</sub>1 Reaction -An alkoxide nucleophile is used instead of iodide in Experiment 1.  Which of the alkoxides is the LEAST sterically hindered? A) B) C) D) Experiment 2The students repeated the procedure followed in Experiment 1 except they added a few drops of each alkyl halide into a separate test tube containing 1 mL of 1% solution of AgNO3 in ethanol at 25°C.  The results observed for this reaction are shown in Table 2.Table 2  Results of the SN1 Reaction
Passage A group of students studied the reactivity of four alkyl halides (R−X) in two nucleophilic substitution reactions.  Nucleophilic substitution reactions can go through one of two mechanisms.  The S<sub>N</sub>2 reaction requires substitution of a leaving group with a nucleophile in a single step (Reaction 1) , and the S<sub>N</sub>1 reaction requires elimination of the leaving group and formation of an intermediate before nucleophilic substitution can occur, resulting in a two-step process (Reaction 2) .R−X + NaI → R−I + NaX↓<strong>Reaction 1</strong>R−X + AgNO<sub>3</sub> → R<sup>+</sup> + AgX↓ + HOCH<sub>2</sub>CH<sub>3</sub> → R−OCH<sub>2</sub>CH<sub>3</sub> + HNO<sub>3</sub><strong>Reaction 2</strong>Experiment 1The students performed the S<sub>N</sub>2 reaction (Reaction 1) by the addition of a few drops of each alkyl halide into a separate test tube containing 1 mL of 15% solution of NaI in acetone at 25°C.  After mixing, they monitored the reaction for the formation of a precipitate (sodium halide salt) .  If no precipitate formed after 5 minutes, they raised the temperature of the reaction to 50°C and again checked for the formation of a precipitate.  Formation of a precipitate indicated the substrate underwent nucleophilic substitution.  The results observed for the Finkelstein reaction are shown in Table 1.<strong>Table 1</strong>  Results of the S<sub>N</sub>2 Reaction Experiment 2The students repeated the procedure followed in Experiment 1 except they added a few drops of each alkyl halide into a separate test tube containing 1 mL of 1% solution of AgNO<sub>3</sub> in ethanol at 25°C.  The results observed for this reaction are shown in Table 2.<strong>Table 2</strong>  Results of the S<sub>N</sub>1 Reaction -An alkoxide nucleophile is used instead of iodide in Experiment 1.  Which of the alkoxides is the LEAST sterically hindered? A) B) C) D)
-An alkoxide nucleophile is used instead of iodide in Experiment 1.  Which of the alkoxides is the LEAST sterically hindered?


A) Passage A group of students studied the reactivity of four alkyl halides (R−X) in two nucleophilic substitution reactions.  Nucleophilic substitution reactions can go through one of two mechanisms.  The S<sub>N</sub>2 reaction requires substitution of a leaving group with a nucleophile in a single step (Reaction 1) , and the S<sub>N</sub>1 reaction requires elimination of the leaving group and formation of an intermediate before nucleophilic substitution can occur, resulting in a two-step process (Reaction 2) .R−X + NaI → R−I + NaX↓<strong>Reaction 1</strong>R−X + AgNO<sub>3</sub> → R<sup>+</sup> + AgX↓ + HOCH<sub>2</sub>CH<sub>3</sub> → R−OCH<sub>2</sub>CH<sub>3</sub> + HNO<sub>3</sub><strong>Reaction 2</strong>Experiment 1The students performed the S<sub>N</sub>2 reaction (Reaction 1) by the addition of a few drops of each alkyl halide into a separate test tube containing 1 mL of 15% solution of NaI in acetone at 25°C.  After mixing, they monitored the reaction for the formation of a precipitate (sodium halide salt) .  If no precipitate formed after 5 minutes, they raised the temperature of the reaction to 50°C and again checked for the formation of a precipitate.  Formation of a precipitate indicated the substrate underwent nucleophilic substitution.  The results observed for the Finkelstein reaction are shown in Table 1.<strong>Table 1</strong>  Results of the S<sub>N</sub>2 Reaction Experiment 2The students repeated the procedure followed in Experiment 1 except they added a few drops of each alkyl halide into a separate test tube containing 1 mL of 1% solution of AgNO<sub>3</sub> in ethanol at 25°C.  The results observed for this reaction are shown in Table 2.<strong>Table 2</strong>  Results of the S<sub>N</sub>1 Reaction -An alkoxide nucleophile is used instead of iodide in Experiment 1.  Which of the alkoxides is the LEAST sterically hindered? A) B) C) D)
B) Passage A group of students studied the reactivity of four alkyl halides (R−X) in two nucleophilic substitution reactions.  Nucleophilic substitution reactions can go through one of two mechanisms.  The S<sub>N</sub>2 reaction requires substitution of a leaving group with a nucleophile in a single step (Reaction 1) , and the S<sub>N</sub>1 reaction requires elimination of the leaving group and formation of an intermediate before nucleophilic substitution can occur, resulting in a two-step process (Reaction 2) .R−X + NaI → R−I + NaX↓<strong>Reaction 1</strong>R−X + AgNO<sub>3</sub> → R<sup>+</sup> + AgX↓ + HOCH<sub>2</sub>CH<sub>3</sub> → R−OCH<sub>2</sub>CH<sub>3</sub> + HNO<sub>3</sub><strong>Reaction 2</strong>Experiment 1The students performed the S<sub>N</sub>2 reaction (Reaction 1) by the addition of a few drops of each alkyl halide into a separate test tube containing 1 mL of 15% solution of NaI in acetone at 25°C.  After mixing, they monitored the reaction for the formation of a precipitate (sodium halide salt) .  If no precipitate formed after 5 minutes, they raised the temperature of the reaction to 50°C and again checked for the formation of a precipitate.  Formation of a precipitate indicated the substrate underwent nucleophilic substitution.  The results observed for the Finkelstein reaction are shown in Table 1.<strong>Table 1</strong>  Results of the S<sub>N</sub>2 Reaction Experiment 2The students repeated the procedure followed in Experiment 1 except they added a few drops of each alkyl halide into a separate test tube containing 1 mL of 1% solution of AgNO<sub>3</sub> in ethanol at 25°C.  The results observed for this reaction are shown in Table 2.<strong>Table 2</strong>  Results of the S<sub>N</sub>1 Reaction -An alkoxide nucleophile is used instead of iodide in Experiment 1.  Which of the alkoxides is the LEAST sterically hindered? A) B) C) D)
C) Passage A group of students studied the reactivity of four alkyl halides (R−X) in two nucleophilic substitution reactions.  Nucleophilic substitution reactions can go through one of two mechanisms.  The S<sub>N</sub>2 reaction requires substitution of a leaving group with a nucleophile in a single step (Reaction 1) , and the S<sub>N</sub>1 reaction requires elimination of the leaving group and formation of an intermediate before nucleophilic substitution can occur, resulting in a two-step process (Reaction 2) .R−X + NaI → R−I + NaX↓<strong>Reaction 1</strong>R−X + AgNO<sub>3</sub> → R<sup>+</sup> + AgX↓ + HOCH<sub>2</sub>CH<sub>3</sub> → R−OCH<sub>2</sub>CH<sub>3</sub> + HNO<sub>3</sub><strong>Reaction 2</strong>Experiment 1The students performed the S<sub>N</sub>2 reaction (Reaction 1) by the addition of a few drops of each alkyl halide into a separate test tube containing 1 mL of 15% solution of NaI in acetone at 25°C.  After mixing, they monitored the reaction for the formation of a precipitate (sodium halide salt) .  If no precipitate formed after 5 minutes, they raised the temperature of the reaction to 50°C and again checked for the formation of a precipitate.  Formation of a precipitate indicated the substrate underwent nucleophilic substitution.  The results observed for the Finkelstein reaction are shown in Table 1.<strong>Table 1</strong>  Results of the S<sub>N</sub>2 Reaction Experiment 2The students repeated the procedure followed in Experiment 1 except they added a few drops of each alkyl halide into a separate test tube containing 1 mL of 1% solution of AgNO<sub>3</sub> in ethanol at 25°C.  The results observed for this reaction are shown in Table 2.<strong>Table 2</strong>  Results of the S<sub>N</sub>1 Reaction -An alkoxide nucleophile is used instead of iodide in Experiment 1.  Which of the alkoxides is the LEAST sterically hindered? A) B) C) D)
D) Passage A group of students studied the reactivity of four alkyl halides (R−X) in two nucleophilic substitution reactions.  Nucleophilic substitution reactions can go through one of two mechanisms.  The S<sub>N</sub>2 reaction requires substitution of a leaving group with a nucleophile in a single step (Reaction 1) , and the S<sub>N</sub>1 reaction requires elimination of the leaving group and formation of an intermediate before nucleophilic substitution can occur, resulting in a two-step process (Reaction 2) .R−X + NaI → R−I + NaX↓<strong>Reaction 1</strong>R−X + AgNO<sub>3</sub> → R<sup>+</sup> + AgX↓ + HOCH<sub>2</sub>CH<sub>3</sub> → R−OCH<sub>2</sub>CH<sub>3</sub> + HNO<sub>3</sub><strong>Reaction 2</strong>Experiment 1The students performed the S<sub>N</sub>2 reaction (Reaction 1) by the addition of a few drops of each alkyl halide into a separate test tube containing 1 mL of 15% solution of NaI in acetone at 25°C.  After mixing, they monitored the reaction for the formation of a precipitate (sodium halide salt) .  If no precipitate formed after 5 minutes, they raised the temperature of the reaction to 50°C and again checked for the formation of a precipitate.  Formation of a precipitate indicated the substrate underwent nucleophilic substitution.  The results observed for the Finkelstein reaction are shown in Table 1.<strong>Table 1</strong>  Results of the S<sub>N</sub>2 Reaction Experiment 2The students repeated the procedure followed in Experiment 1 except they added a few drops of each alkyl halide into a separate test tube containing 1 mL of 1% solution of AgNO<sub>3</sub> in ethanol at 25°C.  The results observed for this reaction are shown in Table 2.<strong>Table 2</strong>  Results of the S<sub>N</sub>1 Reaction -An alkoxide nucleophile is used instead of iodide in Experiment 1.  Which of the alkoxides is the LEAST sterically hindered? A) B) C) D)

Correct Answer:

verifed

Verified

Unlock this answer now
Get Access to more Verified Answers free of charge

Related Questions

Q115: Passage<br>Two key ingredients found in many soaps

Q116: Passage<br>Two key ingredients found in many soaps

Q117: Passage<br>Students used three classification tests to study

Q118: Passage<br>Electrospray ionization mass spectrometry (ESI-MS) employs a

Q119: If a primary alkyl halide and a

Q121: When the compound shown below undergoes an

Q122: Passage<br>Malaria is caused by the parasite Plasmodium

Q123: Which of the following does NOT describe

Q124: Passage<br>The N-terminus of an amino acid must

Q125: Passage<br>Fluorescent amino acids are useful for labeling