Chapter 19: Q57E (page 648)
Draw structures of compounds that fit the following descriptions:
- An ,-unsaturated ketone,
- An -diketone
- An aromatic ketone,
- A diene aldehyde,
Short Answer
(a)

(b)

(c)

(d)

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Chapter 19: Q57E (page 648)
Draw structures of compounds that fit the following descriptions:
(a)

(b)

(c)

(d)

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Propose a mechanism to account for the formation of 3,5-dimethyl pyrazole from hydrazine and 2,4-pentanedione. Look carefully to see what has happened to each carbonyl carbon in going from starting material to product.
Give IUPAC names for the following compounds:
(a)

(b)

(c)

(d)

(e)

(f)

The enamine prepared from acetone and dimethylamine is shown in its
lowest-energy form.
(a) What is the geometry and hybridization of the nitrogen atom?
(b) What orbital on nitrogen holds the lone pair of electrons?
(c) What is the geometric relationship between the p orbitals of the
double bond and the nitrogen orbital that holds the lone pair? Why
do you think this geometry represents the minimum energy?

Compound A, , has an intense IR absorption at 1750 and gives the 13C NMR spectrum shown. Propose a structure for A.

When glucose (Problem 19-52) is treated with NaBH4 , reaction occurs to yield sorbitol, a polyalcohol commonly used as a food additive. Show how this reduction occurs.
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