Nitrogen Containing Organic Compounds

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Nitrogen Containing Organic Compounds

• And
• Other Important Minerals

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The Amino Group

• Nitrogen involves itself in organic chemistry as
  the amino group, -NH2 In this group, there are
  three normal bonds for N, but as an ion it can
  make a fourth
• The N can be attached to up to four carbon chains
  to make amines and ammonium ions, or can be
  substituted for OH in the carboxylic acids to
  make amides

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Amines

• Amines have nitrogen as their central atom, and
  can be classified as primary, secondary, or
  tertiary in a similar fashion to alcohols
• Amines however are 1, 2, or 3 based on what is
  on the N, not on how many Cs are connected to
  the OH carbon

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Amines

• Naming amines is done similarly to the
  ethersname the carbon groups connected to the
  nitrogen
• If the amino group is not the only functional
  group present, it is not named as an amine, since
  it does not have priority. It is then named and
  numbered as a substitution, even if there are
  carbon chains attached to it.

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Examples

• propylamine
• methy ethyl amine
• dimethyl ethyl amine
• aniline
• N-methyl aniline
• N,N-dimethyl aniline

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Basic Properties of Amines

• Just like ammonia acts as a base due to its lone
  pair of electrons on the N
• Amines can do so as well
• The strength of amines as bases depends on the
  type and number of carbon groups attached to the
  N alkyl groups increase the strength, aromatic
  groups decrease the strength

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Reactions of Amines

• With acids they form salts
• With alkyl halides, 3 amines can form quaternary
  ammonium salts
• With nitrites, nitrosamines can be formed
• These nitrosamines are highly carcinogenic, and
  are made from any amine with nitrites or nitrates
  in preserved foods within your stomach

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Homework 14a

• p. 360 CYU all
• p. 373ff 2, 3, 4, 5, 8, 18

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Amides

• Amides are a derivative of carboxylic acids with
  the amino group in place of the hydroxyl. The
  bond between C and N is called the amide linkage
• Naming each is similar to the acids
• formamide acetamide
• butanamide benzamide
• If a carbon group is on the N, it is likewise
  named
• N,N-dimethyl propanamide

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Important Amides

• Urea
• Waste product of metabolism, a combination of
  CO2 and NH3 to protect the body from too much
  acid or base, excreted by the kidneys
• Acetaminophen
• a pain reliever similar to aspirin, but without
  the anti-swelling effect
• LSD
• a hallucinogenic drug which
• blocks serotonin in the brain. Since serotonin
  controls nerve impulses, LSD therefore causes
  freak impulses to create the hallucinations

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Reactions of Amides

• Hydrolysis breaks into an acid and an amine
• Dehydrationcreates a nitrile, useful in organic
  synthesis

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Heterocyclic Compounds

• Nitrogen can be bonded into rings of carbons,
  creating heterocyclic (different atoms) rings
  Many of these are found in biologicl compounds,
  such as in vitamins, hormones, and nucleic acids
• pyrrolidine pyrrole
• pyridine pyrimidine
• purine

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Alkaloids

• Alkaloids have all varieties of nitrogen groups
  in them, and are found throughout the living
  world as control and protection chemicals
• In plants, many alkaloids are part of the plants
  defensive arsenal against pests. Some of these
  have been discovered to have desirable
  physiological effects, but many have negative
  side effects and some are violent poisons
• Some of these are within our bodies to perform
  important functions in order to maintain health
  and safety

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Examples

• Epinephrinealso called adrenaline, important to
  stimulate fast response to danger
• Norepinephrine an important messenger chemical
  between nerve cells
• Amphetamineshave a stimulant action which
  prevents fatigue and relieves nasal congestion

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Other Alkaloids

• Nicotinenarcotic in tobacco, an extremely toxic
  chemical, but continued use builds up tolerance,
  requiring increased dose or frequency of use
• Other alkaloids include caffeine, cocaine,
  morphine, heroin, opium, and the
  barbituratessome which are abused, but all of
  which have physiological and psychological
  effects which under proper supervision can be
  beneficial

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Homework

• p. 365ff CYU all
• p. 374ff 9, 10, 13, 14, 15, 25

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Macrominerals

• Seven elements other than C, H, O, and N are
  important in life chemicals. These are the
  macrominerals Ca, P, K, S, Cl, Na, Mg
• The macrominerals are important both in building
  body structure and in maintaining its proper
  functioning

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Calcium and Phosphorus

• Calcium is important in building bones and teeth,
  along with phosphorus, but also plays an
  important role in maintaining nerve function,
  muscle contraction, body temperature, and blood
  clotting.The level of Ca in the blood must be
  maintained to prevent muscle atrophy and nerve
  problems
• Phosphorus is important in the energy release
  chemical ATP and also in DNA and RNA, the nucleic
  acids

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Mg, K, Na, Cl

• Magnesium, found in our diet in green vegetables
  (primarily in chlorophyll), nuts, cereals and
  seafoods is important in muscle and nerve
  controltoo little can cause muscle spasms and
  heart arrhythmia, too much and muscle and nerve
  paralysis can occur
• Potassium, sodium, and chlorine (as chloride) are
  interrelated in controlling cation/anion balance
  in body fluids. Since K and Na have opposite
  effects to Ca and Mg, it is important to limit
  their intake. Cl is important also in making HCl
  for stomach gastric juice.

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Sulfur

• Sulfur is important as part of the thiol group
  SH, similar to the hydroxyl group. It is found
  in some important amino acids (which form
  proteins) and in an important coenzyme, acetyl
  CoA
• Sulfur groups are the reason for essence of
  skunk, a group of bad smelling chemicals called
  mercaptans

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Trace Elements

• Fourteen other important elements are required in
  very small (trace) amounts in your diet. They
  make parts of hormones, vitamins, enzymes, and
  other control chemicals
• Fluorineimportant in maintaining teeth against
  decay
• Iodineimportant in production of the thyroid
  hormone thyroxine which controls metabolism

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Trace Elements

• Ironinvolved in the oxygen carrier hemoglobin in
  our blood
• Copperimportant part of enzymes which help to
  make hemoglobin
• Cobaltimportant part of Vitamin B-12 which helps
  to create red blood cells

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Homework

• Special Worksheet