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Chapter 12: Q37E (page 354)

Identify all the acidic hydrogens (pKa<25) in the following molecules:

Short Answer

Expert verified

Acidic hydrogens in (a)

Acidic hydrogens in (b)

Acidic hydrogens in (c)

Acidic hydrogens in (d)

Acidic hydrogen in (e)

Acidic hydrogen in (f)

Step by step solution

01

Step 1(a): Acidic hydrogen in molecule (a)

Acidic hydrogens are those which are attached to the 伪-carbon that has electron withdrawing group or bonded to the electronegative atom.

The electron withdrawing group and acidic 伪-hydrogens in the given compound are shown below,

The acidic hydrogens in the compound shown below are bold,

Acidic hydrogens in (a)

02

Step 2(b): Acidic hydrogen in molecule (b)

The electron withdrawing group and acidic 伪-hydrogens in the given compound are shown below,

The acidic hydrogen in the compound shown below are bold,

Acidic hydrogens in (b)

03

Step 3(c): Acidic hydrogen in molecule (c)

The electron withdrawing group and acidic 伪-hydrogens in the given compound are shown below,

The acidic hydrogen in the compound shown below are bold,

Acidic hydrogens in (c)

04

Step 4(d): Acidic hydrogen in molecule (d)

The electron withdrawing group and 伪-hydrogens in the given compound are shown below,

The acidic hydrogen in the compound shown below are bold,

Acidic hydrogens in (d)

05

Step 5(e): Acidic hydrogen in molecule (e)

The electron withdrawing group and acidic 伪-hydrogens in the given compound are shown below,

The acidic hydrogen in the compound shown below are bold,

Acidic hydrogen in (e)

06

Step 6(f): Acidic hydrogen in molecule (f)

The electron withdrawing group and acidic 伪-hydrogens in the given compound are shown below,

The acidic hydrogen in the compound shown below are bold,

Acidic hydrogen in (f)

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Most popular questions from this chapter

Question: The infrared spectrum of the compound with the mass spectrum shown below lacks any significant absorption above 3000cm-1. There is a prominent peak near 1740cm-1and another strong peak near 1200cm-1.Propose a structure consistent with the data.

Question: What functional groups might the following molecules contain?

(a) A compound with a strong absorption at 1710cm-1

(b) A compound with a strong absorption at 1540cm-1

(c) A compound with strong absorptions at 1720cm-1 and 2500 to 3100 cm-1

Name the following alkynes, and predict the products of their reaction

With:

(1) H2in the presence of a Lindlar鈥檚 catalyst

(2) H3O+in the presence of H2SO4

Question: How might you use IR spectroscopy to distinguish between the following pairs of isomers?

a)CH3CH2OHandCH3OCH3b)cyclohexaneand1-hexenec)CH3CH2CO2HandHOCH2CH2CHO

Nonconjugated 尾,纬-unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated 伪,尾-unsaturated isomers. Propose a mechanism for this isomerization.
See all solutions

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