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Draw a structural formula for each compound. (a) \(\mathrm{N}\)-Cyclohexylacetamide (b) 1-Methylpropyl methanoate (c) Cyclobutyl butanoate (d) \(N\)-(1-Methylheptyl)succinimide (e) Diethyl adipate (f) 2-Aminopropanamide

Short Answer

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(a) N-Cyclohexylacetamide The structural formula for N-cyclohexylacetamide is as follows: ``` O || N - C - CH3 | Cyclohexane ring ``` (b) 1-Methylpropyl methanoate The structural formula for 1-methylpropyl methanoate is as follows: ``` O || O - C - CH3 | C - CH(CH3) - CH3 ``` (c) Cyclobutyl butanoate The structural formula for cyclobutyl butanoate is as follows: ``` O || O - C - CH2 - CH2 - CH2 - CH3 | Cyclobutane ring ``` (d) N-(1-Methylheptyl)succinimide The structural formula for N-(1-Methylheptyl)succinimide is as follows: ``` O || - N - CH2 - CH(CH3) - CH2 - CH2 - CH2 - CH2 - CH2 / | C O \\ / N ``` (e) Diethyl adipate The structural formula for diethyl adipate is as follows: ``` O O || || O - C - CH2 - CH2 - CH2 - CH2 - C - O | | C2H5 C2H5 ``` (f) 2-Aminopropanamide The structural formula for 2-aminopropanamide is as follows: ``` O || H2N - C - CH2 - CH3 | NH2

Step by step solution

01

(a) N-Cyclohexylacetamide

N-Cyclohexylacetamide is an acetamide with a cyclohexyl group attached to the nitrogen atom. Here are the steps to draw the structural formula for N-cyclohexylacetamide: 1. Draw a cyclohexane ring. 2. Attach an amide group with two carbons bonded to the nitrogen atom. The first carbon bond to the nitrogen atom and the second carbon is bound to the first carbon by a single bond. This structure represents the acetamide, with the nitrogen atom combining to the cyclohexane ring.
02

(b) 1-Methylpropyl methanoate

1-Methylpropyl methanoate is an ester with the following structure: 1. Draw a methanoate group (\(\mathrm{COOCH_3}\)). 2. Attach a 3-carbon chain with a methyl group on the first carbon to the first oxygen of the methanoate group.
03

(c) Cyclobutyl butanoate

Cyclobutyl butanoate is an ester with the following structure: 1. Draw a butanoate group (\(\mathrm{COOC_3H_7}\)). 2. Replace the hydrogen atom on the first carbon of the butanoate group with a cyclobutane ring.
04

(d) N-(1-Methylheptyl)succinimide

N-(1-Methylheptyl)succinimide is an imide with the following structure: 1. Draw a succinimide ring, which is a 5-membered ring containing a nitrogen atom and an oxygen atom. 2. Replace the hydrogen atom on the nitrogen atom with a 7-carbon chain that has a methyl group on the first carbon.
05

(e) Diethyl adipate

Diethyl adipate is an ester with the following structure: 1. Draw an adipate group, which is hexanedioic acid (\(\mathrm{HOOC(CH_2)_4COOH}\)). 2. Replace both hydrogen atoms on the carboxyl groups with an ethyl group (\(\mathrm{C_2H_5}\)).
06

(f) 2-Aminopropanamide

2-Aminopropanamide is an amide with an amino functional group in the \(\mathrm{\beta}\)-position: 1. Draw a 3-carbon chain called propanamide (\(\mathrm{H_2NCOCH_2CH_3}\)). 2. Replace one hydrogen atom on the second carbon with an amine group (\(\mathrm{-NH_2}\)).

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Most popular questions from this chapter

Using your reaction roadmap as a guide, show how to convert 1-bromopropane and carbon dioxide into 4-heptanone. You must use 1-bromopropane and carbon dioxide as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way.

Barbiturates are prepared by treating a derivative of diethyl malonate with urea in the presence of sodium ethoxide as a catalyst. Following is an equation for the preparation of barbital, a long-duration hypnotic and sedative, from diethyl diethylmalonate and urea. Barbital is prescribed under one of a dozen or more trade names. (a) Propose a mechanism for this reaction. (b) The \(\mathrm{p} K_{\mathrm{a}}\) of barbital is 7.4. Which is the most acidic hydrogen in this molecule? How do you account for its acidity?

The following compound is one of a group of \(\beta\)-chloroamines, many of which have antitumor activity. Describe a synthesis of this compound from anthranilic acid and ethylene oxide.

We have seen two methods for converting a carboxylic acid and an amine into an amide. Suppose that you start instead with a dicarboxylic acid such as hexanedioic acid and a diamine such as 1,6 -hexanediamine. Show how amide formation in this case can lead to a polymer (a macromolecule of molecular weight several thousands times that of the starting materials). As we shall see in Section 29.5A, the material produced in this reaction is the highmolecular-weight polymer nylon 66 , so named because it is synthesized from two 6 -carbon starting materials.

Synthesis of nitriles by nucleophilic displacement of halide from a haloalkane (also called an alkyl halide) is practical only with primary and secondary haloalkanes. It fails with tertiary haloalkanes. Why? What is the major product of the following reaction?

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