E. QUESTIONS, 16 points I The boiling points of the dichlorinated butanes increa
ID: 574954 • Letter: E
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E. QUESTIONS, 16 points I The boiling points of the dichlorinated butanes increase as you go from 1,1 to the 1,4 isomer a. What forces influence the boiling points of these compounds? 2pt Offer an explanation for the increase in BP with the change in dichlorinated butane structure. 2pts b. 2. Your final product mixture contained starting material 1-chlorobutane. Calculate your yield of each dichlorobutane isomer in grams using the mass of product mixture and the Area % (from last column in GC printout) of each dichlorinated product. Show a sample calculation. 4pts 1,1-dichlorobutane 1,2-dichlorobutane g 13-dichlorobutane, .8 g 14-dichlorobutane Sample Calculation 3. The experimental mole ratios of AIBN: sulfuryl chloride: chlorobutane used in this reaction are approximately 0.01:1:2. How does AIBN act to initiate the radical reaction? 2pts a. b. Why is the quantizy/mole ratio of the initiator, AIBN so small? 2pts 4. Two of the four products you obtained via chlorination from 1-chlorobutane are chiral. Draw the structures of the two dichlorinated products that will be chiral. Identify chiral centers with an asterisk (You don't need to draw all R,S configurations.) 2pts a. b. Does radical chlorination produce a single configuration (only R or only S) of a chiral product or a racemic mixture (both R and S)? Explain. 2ptsExplanation / Answer
Ans 1.
(a) In dichlorobutane compound carbon is attached to an electronrgative atom, that is, chlorine which attracts the shared pair of electron towards itself thus, a partial positive charge on hydrogen and a partial negative om chlorine is generated which acts as a dipole. Hence, the forces that govern the boiling point in dichlorinated compound is Van Der Waals dipole-dipole interaction.
(b) In the structure of 1,1-dichlorobutane both the chlorine atoms are attached to the same carbon atom thus nullify each others effect. Therefore, weak dipole will form in 1,1 dichloro compound. However, in 1,4- dichlorobutane, one chlorine is at first position while the other is at fourth position thus, stronger dipole is created at both the places and will have greater boiling point as more energy will required to break the interaction.
Hence, boiling point increases as the distance between both the chlorine increases in the structure.
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