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Chem 3.5 answers #5

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  • 1. CHEMISTRY 3.5 ANSWERSWORKSHEET FIVE ORGANIC Haloalkanes1. (a) 2-chlorobutane (b) 2,3-dichlorobutane2. (a) 2-bromo, 2-methylpropane (3o) (b) 2-bromopropane (2o) (c) 2-chlorobutane (2o) (d) 1-chlorobutane (1o) (e) 2-bromo, 2-methylbutane (3o)(f) 2-bromohexane (2o)3. Haloalkanes have polar C-X bonds which causes them to have some attraction for polar water molecules. However they cannot hydrogen bond to water like alcohols, and so the water molecules prefer to bond to each other rather than to the haloalkane molecules. So the haloalkanes tend to remain in an undissolved layer in the presence of water.4. The boiling points of similar molecular mass organic compounds reflect the strengths of their intermolecular forces. Alkanes have only weak Van der Waals forces between molecules so they are easily separated and have low boiling points. Haloalkanes have polar molecules and so there are stronger permanent dipole interactions between molecules raising their boiling points. Alcohol molecules can hydrogen bond to each other and these strong intermolecular forces give them higher boiling points still.5. (a) CH3CH2Cl + OH- → CH3CH2OH + Cl- (b) If the haloalkane was reacted with aqueous ammonia, the OH- ions present would substitute the halogen and form an alcohol instead of the desired amine. In alcohol, the ammonia molecules do not react to produce OH- ions and so they substitute successfully to make the amine. (c) CH3CH2Cl + NH3 → CH3CH2NH2 + HCl6. (a) CH3CH2CHOHCH3 (b) CH3CHCHCH3 (c) CH3CH2CHCH2 (d) Substitution (e) Elimination Aqueous KOH7. (a) CH3CCl(CH3)2 CH3COH(CH3)2 (b) CH3CHBrCH3 Alcohol/KOH CH3CHCH2 Alcohol/NH3 (c) CH3CH2CH2Cl CH3CH2CH2NH2 (d) CH3CH2CH2CH2Cl Aqueous NaOH CH3CH2CH2CH2OH8. (a) Aqueous KOH (b) Alcoholic NH3 (c) Alcoholic KOH