con org chem - Chemicals from living things were thought to...

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23 • Organic Chemistry Historical Ideas (1 of 16) Chemicals from living things were thought to contain a “ vital force ” that could not be duplicated in the lab. This changed with Friedrich Wöhler who mixed cyanic acid (HCNO) with ammonium hydroxide making ammonium cyanate (NH 4 CNO). C O N H 2 NH 2 urea He usually allowed the salt solution to evaporate overnight, but tried heating it to hurry the process. The result was a crystal that he recognized as urea (H 2 NCONH 2 ). The modern view of organic chemistry is the chemistry of carbon compounds. C is the key element. It can form four bonds and that are very strong bonds due to its small size . 23 • Organic Chemistry Alkane Series -- Saturated Hydrocarbons (2 of 16) The alkanes ( paraffins ) follow the formula: C n H 2n+2 : These molecules contain ONLY single bonds. They are said to be “ saturated ” with hydrogens. Memorize these prefixes also used with alkenes & alkynes. CH 4 meth ane C 6 H 14 hex ane C 2 H 6 eth ane C 7 H 16 hept ane C 3 H 8 prop ane C 8 H 18 oct ane C 4 H 10 but ane C 9 H 20 non ane C 5 H 12 pent ane C 10 H 22 dec ane Given a formula, you can tell that it contains only single bonds because it fits the alkane formula. As the molecules increase in size, they tend to be liquids and 23 • Organic Chemistry Structural Formulas Can Be Misleading (3 of 16) CH 4 , can be drawn using a structural formula . This can be misleading. The molecule is not flat with bond angles of 90 ° . You must be aware of the 3-D structure and the 109.5 bond angles. C H H H H C Cl H H Cl C H H Cl Cl For example, there is only one isomer of dichloromethane, but you can draw it at least two ways. Building models of the molecules is an important part of strengthening this skill. 23 • Organic Chemistry Alkenes and cis- /trans- Isomerism (4 of 16) Alkene s contain 1 double bond. The formula is C n H 2n . They are said to be “ unsaturated (like unsaturated fats). The double bond can be broken and more hydrogens added.
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