Organic Chemistry 9th Edition

Published by Brooks Cole
ISBN 10: 1305080483
ISBN 13: 978-1-30508-048-5

Chapter 1 - Structure and Bonding - Exercises - Page 27c: 30

Answer

(1) CH3-CH2-CH3 (2) NH2-CH3 (3) CH3-CH2-OH & CH3-O-CH3 (4) Br-CH2-CH2-CH3 & CH3-CH(Br)-CH3 (5) CH2=CH-OH, CH3-CHO & ethylene oxide (6) NH2-CH2-CH2-CH3, NH2-CH(CH3)2, CH3-N-CH2-CH3 & N(CH3)3
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Work Step by Step

To solve all the 6 subparts of this problem, let's follow these steps: Step 1: Figure out the unsaturation degree of a hydrocarbon derivative from the equivalent hydrocarbon compound with the same unsaturation degree. But if a compound is a hydrocarbon already, then just directly figure out what that is and skip step 2. Step2: Figure out the structures of all isomers for all possible categories of a hydrocarbon derivative with the unsaturation degree we got in step 1. Step 3: Draw the line-bond structure of the desired compounds. 1) C3H8 is a hydrocarbon which doesn't have any unsaturation degree, so it should be an alkane with 3 carbons, propane. (2) CH5N has the equivalent hydrocarbon compound 'CH4' with the same unsaturation degree (zero). As a rule, the equivalent hydrocarbon compound should have one H atom less than its N containing derivative. So, this compound the problem is asking with one C atom, one N atom and zero unsaturation degree should be an amine, CH3NH2. (3) C2H6O has the equivalent hydrocarbon compound 'C2H6' with the same unsaturation degree (zero) because the equivalent hydrocarbon compound should have the same number of H atom as its oxygen containing derivative. The compound the problem is asking should have two C atoms, one O atom and zero unsaturation degree. Based on different connectivity of carbon and oxygen atoms in the molecular skeleton, the compound can be a saturated alcohol, ethanol (CH3CH2OH) or an open chained ether, CH3OCH3. (4) C3H7Br has the equivalent hydrocarbon compound 'C3H8' with the same unsaturation degree (zero). As a rule, the equivalent hydrocarbon compound should have one H atom more than its Br containing derivative. So, this compound the problem is asking with three C atoms, zero unsaturation degree and one Br atom should be an alkyl bromide. Based on the ways the Br atom substitutes H atoms in propane, the result compound can be either BrCH2CH2CH3 or CH3CH(Br)CH3. (5) C2H4O has the equivalent hydrocarbon compound 'C2H4' (ethylene) with the same unsaturation degree (one). The compound the problem asks should have two C atoms, one O atom and one unsaturation degree. The compound can be an unsaturated alcohol, CH2=CHOH. Or it can be a cyclic ether, ethylene oxide. Or it can be a saturated aldehyde, CH3CHO. (6) C3H9N has the equivalent hydrocarbon compound 'C3H8' with the same unsaturation degree (zero). The compound the problem asks with three C atoms, one N atom and zero unsaturation degree can be a primary amine, NH2CH2CH2CH3 or NH2CH(CH3)2; or it can be a secondary amine, CH3NHCH2CH3; or can be a tertiary amine, N(CH3)3.
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