Video Solution: The overall equation for the addition of HCl to alkenes is: ...

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The overall equation for the addition of HCl to alkenes is:  

 If the transition state for proton transfer from HCl to the alkene (arrow  5 ) resembles a carbocation and this step is rate-determining, what should be the effect of alkene structure on the rate of the overall reaction?

 Fastest rate                                    Slowest rate

A. H2C=CH2    CH3CH=CHCH3    (CH3)2C=C(CH3)2

B. CH3CH=CHCH3    (CH3)2C=C(CH3)2    H2C=CH2

C. CH3CH=CHCH3    H2C=CH2    (CH3)2C=C(CH3)2

D. (CH3)2C=C(CH3)2    CH3CH=CHCH3    H2C=CH2

Rank the substrates below in terms of relative SN1 reaction rate. (1 = fastest, 4 = slowest)

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For the following carbocations, rank them from 1-3 according to overall carbocation stability, with a 1 under the LEAST STABLE CARBOCATION and a 3 under the MOST STABLE CARBOCATION.

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When 2-methylbutene is reacted with hydrochloric acid, where does the carbocation form and why?

1. The carbocation forms at the tertiary position because of steric hindrance.

2. The carbocation forms at the secondary position because of hyperconjugation from neighboring carbons.

3. The carbocation forms at the primary position because nature says so.

4. The carbocation forms at the tertiary position because of hyperconjugation from neighboring carbons.

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Rank the following molecules in order of increasing relative rate of SN1 solvolysis with methanol and heat (slowest to fastest reacting).

A) 5 < 4 < 3 < 2 < 1

B) 1 < 2 < 5 < 4 < 3

C) 2 < 3 < 4 < 1 < 5

D) 3 < 2 < 4 < 5 < 1

E) 2 < 3 < 4 < 5 < 1

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Circle the correct answer

 

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The following statements are true. Choose from among the following three possibilities and in the space provided, write the letter of the one or more phenomena that best explain the true statement.

A. The inductive effect     B. Hyperconjugation     C. Resonance delocalization of a charged species

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The driving force for carbocation rearrangements is that the less stable 2° carbocation is converted into a more stable 3° carbocation ( True or False )

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Identify which of the following substrates will undergo an SN1 reaction more rapidly. Explain your choice

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Which two compounds ionize with loss of bromide ion to form the same carbocation?

a. 1 and 2

b. 2 and 3

c. 1 and 4

d. 3 and 4

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Which alcohol is dehydrated fastest in concentrated H2SO4?

 

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Which carbocation is the most stable?

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Rank the following carbocations in order of stability: 

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