Chapter 7: Q7-54E (page 219)
Rank the carbocations below in terms of increasing stability:

Short Answer
a)

b)

c)

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Chapter 7: Q7-54E (page 219)
Rank the carbocations below in terms of increasing stability:

a)

b)

c)

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The isobutyl cation spontaneously rearranges to the tert-butyl cation by a hydride shift. Is the rearrangement exergonic or endergonic? Draw what you think the transition state for the hydride shift might look like according to the Hammond postulate.

Retin A, or retinoic acid, is a medication commonly used to reduce wrinkles and treat severe acne. How many different isomers arising from double-bond isomerizations are possible?

Which of the following compounds can exist as pairs of cis-trans isomers? Draw each cis-trans pair, and indicate the geometry of each isomer.
Predict the major product in each of the following reactions:

Draw structures corresponding to the following systematic names:
(a)(4E)-2, 4-Dimethyl-1, 4-hexadiene
(b)cis-3, 3-Dimethyl-4-propyl-1, 5-octadiene
(c)4-Methyl-1, 2-pentadiene
(d)(3E,5Z)-2, 6-Dimethyl-1, 3, 5,7-octatetraene
(e)3-Butyl-2-heptene
(f)trans-2, 2, 5, 5-Tetramethyl-3-hexene
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