Chapter 11 - CHAPTER 11 INTRODUCTION TO ORGANIC CHEMISTRY...

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CHAPTER 11 INTRODUCTION TO ORGANIC CHEMISTRY 11.11 The structures are as follows: CH 3 CH 2 CH 2 CH 3 CH 2 CH 2 CH 2 CH 3 CH 2 CH CH 3 CH CH 3 CH 3 CH 2 CH 3 CH 2 CH CH 3 CH 3 CH 2 CH 2 CH 3 CH 2 CH CH 3 CH 3 CH 2 CH 3 CH 2 CH 3 CH 2 C CH 3 CH 3 CH 3 CH 2 CH 3 CH 2 C CH 3 CH 3 CH 2 CH 3 CH CH 3 CH 3 CH CH 3 CH 3 CH 3 C CH 3 CH 3 CH CH 3 CH 3 CH 2 CH CH 2 CH 3 CH 3 CH 2 11.12 Strategy: For small hydrocarbon molecules (eight or fewer carbons), it is relatively easy to determine the number of structural isomers by trial and error. Solution: We are starting with n -pentane, so we do not need to worry about any branched chain structures. In the chlorination reaction, a Cl atom replaces one H atom. There are three different carbons on which the Cl atom can be placed. Hence, three structural isomers of chloropentane can be derived from n pentane: CH 3 CH 2 CH 2 CH 2 CH 2 Cl CH 3 CH 2 CH 2 CHClCH 3 CH 3 CH 2 CHClCH 2 CH 3 11.13 The molecular formula shows the compound is either an alkene or a cycloalkane. (Why?) You can't tell which from the formula. The possible isomers are: H C H H H H H HH C CC H H C H H H H H H C H H H H H H C C C C The structure in the middle (2 butene) can exist as cis or trans isomers. There are two more isomers. Can you find and draw them? Can you have an isomer with a double bond and a ring? What would the molecular formula be like in that case?
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CHAPTER 11: INTRODUCTION TO ORGANIC CHEMISTRY 220 11.14 Both alkenes and cycloalkanes have the general formula C n H 2 n . Let’s start with C 3 H 6 . It could be an alkene or a cycloalkane. C H H C CH 3 H C C C H H H H H H Now, let’s replace one H with a Br atom to form C 3 H 5 Br. Four isomers are possible. C H Br C 3 H C H C 3 H C H H C 2 H C C C H H H H H There is only one isomer for the cycloalkane. Note that all three carbons are equivalent in this structure. 11.15 The straight chain molecules have the highest boiling points and therefore the strongest intermolecular attractions. Theses chains can pack together more closely and efficiently than highly branched structures. This allows intermolecular forces to operate more effectively and cause stronger attractions. 11.16 (a) This compound could be an alkene or a cycloalkane ; both have the general formula, C n H 2 n . (b) This could be an alkyne with general formula, C n H 2 n 2 . It could also be a hydrocarbon with two double bonds (a diene). It could be a cyclic hydrocarbon with one double bond (a cycloalkene). (c) This must be an alkane ; the formula is of the C n H 2 n + 2 type. (d) This compound could be an alkene or a cycloalkane ; both have the general formula, C n H 2 n . (e) This compound could be an alkyne with one triple bond, or it could be a cyclic alkene (unlikely because of ring strain). 11.17 staggered eclipsed The staggered conformation is more stable.
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Chapter 11 - CHAPTER 11 INTRODUCTION TO ORGANIC CHEMISTRY...

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