Arrange the following in order of increasing boiling point and explain your reasoning (hint: structures shown are skeletal structures and may not show the complete picture) Explain your answer, being sure to use the ideas of forces and energy. 7. A в D нн нн нн -он н-с-с-н н H H-C-C-OH HO-C-c-OH H-C-H н-с-он нн нн нн

Figure 3-1 1 А. СНЗ с. CHz CH3 CH-CH-CH3 CH ₂ CH 3 в. н D. CH CH3 . тоен - сненсне енз СнЗ

I. List all the IMFS that are present in a pure sample of substance A below. The Lewis structure of a molecule is shown. H -C C-H | | H II. Draw one example of substance A acting as a H-bond donor with water. Make sure your H- bond starts and ends in the right places. If the molecule can't act as a H-bond donor, write "not possible." II. Draw one example of substance A acting as a H-bond acceptor with water. Make sure your H-bond starts and ends in the right places. If the molecule can't act as a H-bond acceptor, write "not possible." IV. List all the IMF that are present in a pure sample of substance B below. The Lewis structure of a molecule is shown. H H. C N. H H. H V. Compare substance A and substance B. Which would you expect to have the highest boiling point? Briefly explain why (in about 1 sentence). IIC- :O:

1. LDA, -78°C 2 CHIẾ 1. NaH 2. 1. LDA, -78°C 2. CH_Br 3. LDA, -78°C 4. CH_Br Br 1. NaH 2. Br

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Figure 11-5 A. 1) Hg(0Ac)₂, H₂O B. 1) BH 3 C. D. 2) Na B H4 2) H₂O₂, OH, H₂O 2) OH, DMF ) 1) H Br 1) Hg (0Ac) ₂, H₂O H Br → 3) HBr 3) Ts Cl 2) Brz 3) TSCI ) Br H₂ SO4 4) Br¯ 4) HBr

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