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Organic Chemistry I - Alkyl Halides and E1 and E2 Mechanism | C 306, Assignments of Organic Chemistry

Material Type: Assignment; Class: Organic Chemistry I; Subject: Chemistry; University: South Carolina State University; Term: Unknown 1989;

Typology: Assignments

Pre 2010

Uploaded on 08/19/2009

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Name: . . . . . . .. . . . . . . Date: . . . . . .. . . . .
DEPARTMENT OF BIOLOGICAL AND PHYSICAL SCIENCEA
Phone: (803) 536-8513 and 536-7105
FAX: (803) 536-4685 & 536-8436
Organic Chemistry I, C306: Alkyl halides and E1 and E2 Mechanism
Choose the one alternative that best completes the statement or answers the question.
1) Which of the following statements correctly describe(s) E1 reactions of alkyl halides (RX)?
I. Rate = k[base] . II. Rate = k[base][RX]. III. Rate = k[RX].
IV. The reactions occur in two or more distinct steps.. Rearrangements are sometimes seen.
A) III and V B) III, IV, and V C) I only D) I, IV, and V E) II and IV
2) Which of the following mechanisms (SN1, SN2, E1, E2) feature(s) a carbocation intermediate?
A) SN2 only B) E1 only C) E2 only D) SN1 only E) both SN1 and E1
3) Predict the two most likely mechanisms for the reaction of 2-iodohexane with sodium ethoxide.
A) E1 and SN1 B) SN2 and SN1 C) E1 and E2 D) SN2 and E2 E) E2 and SN1
4) Which of the following alkyl chlorides is least likely to undergo rearrangement during a solvolysis reaction?
A) 2-chloro-4-methylpentane B) 2-chloro-3-methylpentane C) trans-1-chloro-2-ethylcyclohexane
D) 2-chloro-2-methylpentane E) cis-1-chloro-2-ethylcyclohexane
5) How many distinct alkene products are possible when the alkyl iodide below undergoes E2 elimination? Show the step-
by-step mechanism for each alkene in a separated page. 5 extra point for each mechanism.
A) 1 B) 2 C) 3
D) 4 E) 5
Write your answer in the space provided or on a separate sheet of paper.
6) What is Saytzeff's rule?
7) Why does CH2=CHCHBrCH3 undergo solvolysis much more rapidly than 2-bromobutane? (Show the resonance
structures)
8) Provide the structure of the major organic product which results when 2-bromo-2-methylbutane is treated with sodium
ethoxide. (Show the step-by-step mechanism. 5 extra point for each mechanism.)
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Name:...... ........ Date:..... ......

DEPARTMENT OF BIOLOGICAL AND PHYSICAL SCIENCEA

Phone: (803) 536-8513 and 536-

FAX: (803) 536-4685 & 536-

Organic Chemistry I, C306: Alkyl halides and E1 and E2 Mechanism

Choose the one alternative that best completes the statement or answers the question.

  1. Which of the following statements correctly describe(s) E1 reactions of alkyl halides (RX)?

I. Rate = k[base]. II. Rate = k[base][RX]. III. Rate = k[RX].

IV. The reactions occur in two or more distinct steps.. Rearrangements are sometimes seen.

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

  1. Which of the following mechanisms (S N

1, S

N

2, E1, E2) feature(s) a carbocation intermediate?

A) S

N

2 only B) E1 only C) E2 only D) S N

1 only E) both S N

1 and E

  1. Predict the two most likely mechanisms for the reaction of 2-iodohexane with sodium ethoxide.

A) E1 and S N

1 B) S

N

2 and S N

1 C) E1 and E2 D) S N

2 and E2 E) E2 and S N

  1. Which of the following alkyl chlorides is least likely to undergo rearrangement during a solvolysis reaction?

A) 2-chloro-4-methylpentane B) 2-chloro-3-methylpentane C) trans -1-chloro-2-ethylcyclohexane

D) 2-chloro-2-methylpentane E) cis -1-chloro-2-ethylcyclohexane

  1. How many distinct alkene products are possible when the alkyl iodide below undergoes E2 elimination? Show the step-

by-step mechanism for each alkene in a separated page. 5 extra point for each mechanism.

A) 1 B) 2 C) 3

D) 4 E) 5

Write your answer in the space provided or on a separate sheet of paper.

  1. What is Saytzeff's rule?

  2. Why does CH 2

=CHCHBrCH 3

undergo solvolysis much more rapidly than 2-bromobutane? (Show the resonance

structures)

  1. Provide the structure of the major organic product which results when 2-bromo-2-methylbutane is treated with sodium

ethoxide. ( Show the step-by-step mechanism. 5 extra point for each mechanism.)

Name:

  1. Provide the structure and step-by-step mechanism of the major alkene product of the reaction below.

  2. Provide the structure and step-by-step mechanism of the major organic product in the following reaction.

  3. Provide the structure and step-by-step mechanism of the major organic product in the following reaction.

  4. Provide the structure of the major organic product which results in the following reaction.