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Chapter 20: Q19P a. (page 1066)

Show how you would synthesize the following compounds from the appropriate carboxylic acids or acid derivatives.

(a)

(b)

(c)

Short Answer

Expert verified

(a)

Step by step solution

01

Carboxylic acids or acid derivatives

Carboxylic acids are the COOH- containing compounds, and acid derivatives are the compounds formed when the OH group of a carboxylic acid is replaced by Cl (acid chloride) or - NH2(amide).There are three types of acid derivatives: acid halides, esters, and amides.

02

Synthesis of phenylacetic acid

(a) Isopropyl alcohol is synthesized when phenylacetic acid is treated with LiAlH4 and further with H3O+. Another method is by treating phenylacetic acid with B2H6 and then with H3O+.


Synthesis of phenylacetic acid

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Most popular questions from this chapter

Given the structure of ascorbic acid (vitamin C):

(a) Is ascorbic acid a carboxylic acid?

(b) Compare the acid strength of ascorbic acid (pKa=4.71) with acetic acid.

(c) Predict which proton in ascorbic acid is the most acidic.

(d) Draw the form of ascorbic acid that is present in the body (aqueous solution, pH = 7.4).

(a) Propose a mechanism for the following reaction:

(b) Use the bond-dissociation enthalpies given in Table 4-2 (page 203) to calculate the value of ∆H° for each step shown in your mechanism. (The BDE for is about 280 kJ/mol, or 67 kcal/mol.) Calculate the overall value of ∆H° for the reaction. Are these values consistent with a rapid free-radical chain reaction?

Question: The IR spectrum of trans-oct-2-enoic acid is shown. Point out the spectral characteristics that allow you to tell that this is a carboxylic acid, and show which features lead you to conclude that the acid is unsaturated and conjugated.

The IR spectrum of trans-oct-2-enoic acid is shown. Point out the spectral characteristics that allow you to tell that this is a carboxylic acid, and show which features lead you to conclude that the acid is unsaturated and conjugated.

Show how you would synthesize the following compounds, starting with acetylene and any compounds containing no more than four carbon atoms.

(a)hex-1-yne

(b)hex-2-yne

(c)cis-hex-2-ene

(d)trans-hex-2-ene

(e)1,1-dibromohexane

(f)2,2-dibromohexane

(g)pentanal, CH3CH2CH2CH2CHO

(h)pentan-2-one, CH3-CO-CH 2CH2 CH3

(i) (+/)-3,4-dibromohexane

(j)meso-butan-2,3-diol

(k)2-methylhex-3-yn-2-ol
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