Chapter 17: Problem 17.3 (page 646)
Give the IUPAC name for each compound.
(a)

(b)

(c)

(d)

Short Answer
Answer
- m-1,3-diisopropylbenzene
- 1-sec-butyl-4-ethylbenzene
- m-butylphenol
- 2-bromo-5-chlorotoulene
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Chapter 17: Problem 17.3 (page 646)
Give the IUPAC name for each compound.
(a)

(b)

(c)

(d)

Answer
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Question: You have a sample of a compound of molecular formula , which has a benzene ring substituted by two groups, and , and exhibits the given NMR. What disubstituted benzene isomer corresponds to these data?

What orbitals are used to form the labeled bonds in the following molecule? Of the labeled bonds, which is the shortest?

Question: Answer the following questions about curcumin, a yellow pigment isolated from turmeric, a tropical perennial in the ginger family and a principal ingredient in curry powder.

a. In Chapter 11 we learned that most enols, compounds that contain a hydroxy group bonded to a C=C, are unstable and tautomerize to carbonyl groups. Draw the keto form of the enol of curcumin, and explain why the enol is more stable than many other enols.
b. Explain why the enol O-H proton is more acidic than an alcohol O-H proton.
c. Why is curcumin colored?
d. Explain why curcumin is an antioxidant.
Question: Classify each compound as aromatic, antiaromatic, or not aromatic.
Question: Draw additional resonance structures for each species.
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