Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 22: Problem 60

Draw the isomer(s) specified. There may be more than one possible isomer for each part. a. a cyclic compound that is an isomer of trans-2-butene b. an ester that is an isomer of propanoic acid c. a ketone that is an isomer of butanal d. a secondary amine that is an isomer of butylamine e. a tertiary amine that is an isomer of butylamine f. an ether that is an isomer of 2 -methyl-2-propanol g. a secondary alcohol that is an isomer of 2-methyl-2-propanol

Short Answer

Expert verified
a. Cyclobutane: \[ \chemfig{*4(-C(-H)(=[:30]-H)(-H)-C(-H)-)} \] b. Methyl acetate: \( CH_3COOCH_3 \) c. Propanone (acetone): \( CH_3COCH_3 \) d. N-methylpropylamine: \( CH_3CH_2CH_2NHCH_3 \) e. N,N-dimethylethylamine: \( (CH_3)_2NCH_2CH_3 \) f. Methoxypropane: \( CH_3OCH_2CH_2CH_3 \) g. 2-butanol: \( CH_3CH(OH)CH_2CH_3 \)

Step by step solution

01

a. A cyclic compound that is an isomer of trans-2-butene

Trans-2-butene (CH3-CH=CH-CH3) has a molecular formula of C4H8. We are looking for a cyclic compound with the same molecular formula. A cyclobutane (four membered ring) meets the requirement, as shown below: \[ \text{Cyclobutane: }\chemfig{*4(-C(-H)(=[:30]-H)(-H)-C(-H)-)} \]
02

b. An ester that is an isomer of propanoic acid

Propanoic acid (CH3-CH2-COOH) has a molecular formula of C3H6O2. We are looking for an ester with the same molecular formula. A methyl acetate meets the requirement, as shown below: \[ \text{Methyl acetate: } CH_3COOCH_3 \]
03

c. A ketone that is an isomer of butanal

Butanal (CH3-CH2-CH2-CHO) has a molecular formula of C4H8O. We are looking for a ketone with that same molecular formula. Propanone (also known as acetone) meets the requirement, as shown below: \[ \text{Propanone (acetone): } CH_3COCH_3 \]
04

d. A secondary amine that is an isomer of butylamine

Butylamine (CH3-CH2-CH2-CH2-NH2) has a molecular formula of C4H11N. We are looking for a secondary amine with that same molecular formula. N-methylpropylamine meets the requirement, as shown below: \[ \text{N-methylpropylamine: } CH_3CH_2CH_2NHCH_3 \]
05

e. A tertiary amine that is an isomer of butylamine

As mentioned before, butylamine has a molecular formula of C4H11N. We are looking for a tertiary amine with that same molecular formula. N,N-dimethylethylamine meets the requirement, as shown below: \[ \text{N,N-dimethylethylamine: } (CH_3)_2NCH_2CH_3 \]
06

f. An ether that is an isomer of 2-methyl-2-propanol

2-methyl-2-propanol (CH3-C(CH3)2-OH) has a molecular formula of C4H10O. We are looking for an ether with that same molecular formula. Methoxypropane meets the requirement, as shown below: \[ \text{Methoxypropane: } CH_3OCH_2CH_2CH_3 \]
07

g. A secondary alcohol that is an isomer of 2-methyl-2-propanol

As mentioned before, 2-methyl-2-propanol has a molecular formula of C4H10O. We are looking for a secondary alcohol with that same molecular formula. 2-butanol meets the requirement, as shown below: \[ \text{2-butanol: } CH_3CH(OH)CH_2CH_3 \]

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Write the sequence of all possible tetrapeptides composed of the following amino acids. a. two phenylalanines and two glycines b. two phenylalanines, glycine, and alanine

Polycarbonates are a class of thermoplastic polymers that are used in the plastic lenses of eyeglasses and in the shells of bicycle helmets. A polycarbonate is made from the reaction of bisphenol A (BPA) with phosgene \(\left(\mathrm{COCl}_{2}\right)\) : Phenol \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}\right)\) is used to terminate the polymer (stop its growth). a. Draw the structure of the polycarbonate chain formed from the above reaction. b. Is this reaction a condensation or an addition polymerization?

There is only one compound that is named 1,2 -dichloroethane, but there are two distinct compounds that can be named 1,2-dichloroethene. Why?

Sorbic acid is used to prevent mold and fungus growth in some food products, especially cheeses. The systematic name for sorbic acid is 2,4-hexadienoic acid. Draw structures for the four geometrical isomers of sorbic acid.

For each of the following, fill in the blank with the correct response. All of these fill-in-the-blank problems pertain to material covered in the sections on alkanes, alkenes and alkynes, aromatic hydrocarbons, and hydrocarbon derivatives. a. The first "organic" compound to be synthesized in the laboratory, rather than being isolated from nature, was ____ ,which was prepared from _______. b. An organic compound whose carbon-carbon bonds are all single bonds is said to be _________. c. The general orientation of the four pairs of electrons around the carbon atoms in alkanes is _______. d. Alkanes in which the carbon atoms form a single unbranched chain are said to be _______ alkanes. e. Structural isomerism occurs when two molecules have the same number of each type of atom but exhibit different arrangements of the _____ between those atoms. f. The systematic names of all saturated hydrocarbons have the ending _____ added to a root name that indicates the number of carbon atoms in the molecule. g.For a branched hydrocarbon, the root name for the hydrocarbon comes from the number of carbon atoms in the _______ continuous chain in the molecule. h.The positions of substituents along the hydrocarbon framework of a molecule are indicated by the _______ of the carbon atom to which the substituents are attached. i. The major use of alkanes has been in _______ reactions, as a source of heat and light. j. With very reactive agents, such as the halogen elements, alkanes undergo ________ reactions, whereby a new atom replaces one or more hydrogen atoms of the alkane. k. Alkenes and alkynes are characterized by their ability to undergo rapid, complete _______ reactions, by which other atoms attach themselves to the carbon atoms of the double or triple bond. l. Unsaturated fats may be converted to saturated fats by the process of __________. m. Benzene is the parent member of the group of hydrocarbons called ______ hydrocarbons. n.An atom or group of atoms that imparts new and characteristic properties to an organic molecule is called a ______ group. o.A _______ alcohol is one in which there is only one hydrocarbon group attached to the carbon atom holding the hydroxyl group. p.The simplest alcohol, methanol, is prepared industrially by the hydrogenation of ______. q. Ethanol is commonly prepared by ______ the of certain sugars by yeast. r. Both aldehydes and ketones contain ______ the but they differ in where this group occurs along the hvdrocarbon chain. s. Aldehydes and ketones can be prepared by of______ the corresponding alcohol. t. Organic acids, which contain the ________ group, are typically weak acids. u. The typically sweet-smelling compounds called ____ result from the condensation reaction of an organic acid with an ________.
See all solutions

Recommended explanations on Chemistry Textbooks

Physical Chemistry

Read Explanation

Chemical Analysis

Read Explanation

Kinetics

Read Explanation

Inorganic Chemistry

Read Explanation

Nuclear Chemistry

Read Explanation

Making Measurements

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free