Question

Please explain and solve a-g and I will rate for those that do.

Thanks.

Answer the following questions for CH₃CHOHCH=CH₂:

a) Write the full dash structure formula.

b) Show all nonbonding electron pairs on your dash formula.

c) Indicate any non-zero formal charges.

d) Label the hybridizations for each carbon and the oxygen.

e) Draw a 3D structure using solid wedges for bonds coming out of the plane and dashed wedges for bonds behind the plane of the paper.

f) Label the bond angles in the 3D drawing.

g) Draw a bond-line formula.

Answer 1

Carboxylic acids occur widely in nature, often combined with alcohols or other functional groups, as in fats, oils, and waxes. They are components of manyfoods, medicines, and household products (Figure 15.1 "Carboxylic Acids in the Home"). Not surprisingly, many of them are best known by common names basedon Latin and Greek words that describe their source. What you learn in this chapter about the chemistry of carboxylic acids will help you understandbiochemistry

The simplest carboxylic acid, formic acid (HCOOH), was first obtained by the distillation of ants (Latin formica, meaning “ant”). The bites of some antsinject formic acid, and the stings of wasps and bees contain formic acid (as well as other poisonous materials).

The next higher homolog is acetic acid, which is made by fermenting cider and honey in the presence of oxygen. This fermentation produces vinegar, asolution containing 4%–10% acetic acid, plus a number of other compounds that add to its flavor. Acetic acid is probably the most familiar weak acid usedin educational and industrial chemistry laboratories.

Note
Pure acetic acid solidifies at 16.6°C, only slightly below normal room temperature. In the poorly heated laboratories of the late 19th and early 20thcenturies in northern North America and Europe, acetic acid often “froze” on the storage shelf. For that reason, pure acetic acid (sometimes calledconcentrated acetic acid) came to be known as glacial acetic acid, a name that survives to this day.
The third homolog, propionic acid (CH3CH2COOH), is seldom encountered in everyday life. The fourth homolog, butyric acid (CH3CH2CH2COOH), is one of themost foul-smelling substances imaginable. It is found in rancid butter and is one of the ingredients of body odor. By recognizing extremely small amountsof this and other chemicals, bloodhounds are able to track fugitives. Models of the first four carboxylic acids are shown in "Ball-and-Stick Models ofCarboxylic Acids".

arboxylic acids feature a carbon atom doubly bonded to an oxygen atom and also joined to an OH group. The four acids illustrated here are formic acid (a),acetic acid (b), propionic acid (c), and butyric acid (d).
The acid with the carboxyl group attached directly to a benzene ring is called benzoic acid (C6H5COOH).

The common names of carboxylic acids use Greek letters (a, ß, ?, d, and so forth), not numbers, to designate the position of substituent groups in acids.These letters refer to the position of the carbon atom in relation to the carboxyl carbon atom.

In the nomenclature system of the International Union of Pure and Applied Chemistry (IUPAC), the parent hydrocarbon is the one that corresponds to thelongest continuous chain (LCC) containing the carboxyl group. The -e ending of the parent alkane is replaced by the suffix -oic and the word acid. Forexample, the carboxylic acid derived from pentane is pentanoic acid (CH3CH2CH2CH2COOH). As with aldehydes, the carboxyl carbon atom is counted first;numbers are used to indicate any substituted carbon atoms in the parent chain.
Note
Greek letters are used with common names; numbers are used with IUPAC names.



CH4 Methane CH4
CH3CH3 Ethane C2H6
CH3CH2CH3 Propane C3H8
CH3CH2CH2 CH3 Butane C4H10 CH3(CH2)2CH3
CH3CH2CH2 CH2 CH3 Pentane C5H12 CH3(CH2)3CH3
CH3CH2CH2 CH2 CH2 CH3 Hexane C6H14 CH3(CH2)4CH3
CH3CH2CH2 CH2 CH2 CH2 CH3 Heptane C7H16 CH3(CH2)5CH3
CH3CH2CH2 CH2 CH2 CH2 CH2 CH3 Octane C8H18 CH3(CH2)6CH3
CH3CH2CH2CH2CH2CH2CH2CH2CH3 Nnonane C9H20 CH3(CH2)7CH3
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 Decane C10H22 CH3(CH2)8CH3
Substituent Groups
CH3- Methyl Cl- Chloro
CH3CH2- Ethyl Br- Bromo
CH3CH2CH3 Propyl I- Iodo
CH3CH2CH2 CH2- Butyl F- fluoro
CH3CH2CH2 CH2 CH2- Pentyl -NO2 Nitro
CH3CH2CH2 CH2 CH2 CH2- Hexyl
Consider the following molecule and name it using the following procedures.

3,3,4-tribromo-6-chloro-2-methyloctane
1 When naming a hydrocarbon, you find the longest continuous carbon chain and number it giving the lowest possible numbers to the substituent groups. Thislongest chain is called the parent molecule.
2 Give the name of substituent groups in alphabetic order giving the number of the carbon that EACH substituent group is attached to, and indicate thenumber of EACH type of substituent by using the prefixes: di, tri, tetra, penta, hexa, hepta, octa, nona, deca etc. Commas go between numbers and dashes gobetween numbers and words. Try these:


3 When hydrocarbons are cyclic, that is the ends are attached to form a closed carbon ring, the prefix cyclo- is given to the parent hydrocarbon. Numbersare given to give the lowest possible numbers to the substituents.

Problem 1: What is the general formula for linear alkanes. What is the general formula for cyclic alkanes.
Problem 2: Give all the possible straight chain alkane isomers for C6H14 and name each.
Problem 3: Give all the possible cycloalkane isomers for C6H12 and name each.
Alkenes
Alkenes are hydrocarbons having carbon-carbon double bonds.
CH2=CH2 Ethene
CH2=CHCH3 Propene
CH2=CHCH2CH3 1-Butene
CH3CH=CHCH3 2-Butene
CH2=CHCH2CH2CH3 1-Pentene
CH3CH=CHCH2CH3 2-Pentene
CH2=CHCH2CH2CH2CH3 1-Hexene
CH3CH=CHCH2CH2CH3 2-Hexene
CH3CH2CH= CHCH2CH3 3-Hexene etc.
When naming alkenes the lowest number is given to the double bond in the molecule. Double bonds take precedence over other substituent groups.
Problem 4: Name the following:
CH3CH2CH=CHCHClCCl2CH2CHClCH3
CH3CH2CHClC(CH3)ClCCl2CH=CH2

CH3CH2CH= CHCHClCCl2CH2CCl=CH2
Since carbon-carbon double bonds can’t rotate, stereoisomerisms (cis-trans) isomers exists.

Cis-1,2-dichloro ethene Trans-1,2-dichloro ethene
Problem 5: Give all possible alkene isomers for C6H12 and name each isomer.
Problem 6: What is the general formula for alkenes?
Problem 7: What is the general formula for a cycloalkene?
Problem 8: What is the general formula for a diene?
Aromatic Hydrocarbons
Aromatic hydrocarbons are cyclic hydrocarbons having alternating double bonds whose number of p-electrons is 4n+2 where n can be 0,1,2,3,4...

Benzene
Each sp2 hybridized carbons has a leftover p-orbital in which 3 pairs of electrons exist above and below the plane of the carbons in a p-bonding network.This p-network delocalizes (spreads out) the electrons thus reducing the energy of the system. The two resonance forms of benzene are shown above; however,neither is correct since the electron waves are spread out evenly throughout the p-system.
When naming substituted benzenes, the lowest number is given to the substituent group(s), the names of the substituent groups is given in alphabetic orderand the name benzene or the particular benzene derivative is given last.
Benzene Derivatives Ø = C6H5 (Phenyl group)
Ø-OH Phenol Note: The lowest number is given to
Ø-NH2 Analine the functional group.
Ø-CH3 Toluene
Ø-CHO Benzaldehyde
Ø-CO2H Benzoic acid
Problem 9: Name the follwoing:



Another nomenclature that is particular to benzene derivatives is the ortho, para, meta designation. Ortho indicates the #2 position relative to anothersubstituent group or functional group. Meta indicates the #3 position relative to another substituent group or functional group. Para indicates the #4position relative to another substituent group or functional group. When giving this designation o-, p- and m- are used in front of the substituent group’sname.
Problem 10: Give two names for each of the following.



Derivatives of Hydrocarbons: Functional Groups
General Formula General Class Example Example name
R-X X= Cl, Br, I, F Organic halide CH3CH2-Br Ethyl bromide
R-OH Alcohol CH3CH2-OH Ethanol or Ethyl Alcohol
R-O-R Ether CH3CH2-O-CH2CH3 Diethyl ether
R-COH Aldehyde CH3CH2-COH Ethanal
R-COR’ Ketone CH3CH2-CO-CH2CH3 3-pentanone
R-COOH Carboxylic acid CH3CH2-COOH Propanoic acid
R-COOR’ Ester CH3COOCH3 Methylacetate
R-NH2, R-N, R-N Amine CH3CH2-NH2 Etylamine
R-CON Amide CH3CONHCH3 N-methylacetamide
Alcohols
Alcohols are hydrocarbons having an -OH group. Alcohols have three general classes: Primary 1°, secondary 2° and tertiary 3°.
1° 2° 3°

Alcohols can be formed by the addition of water across a double bond. Under the reaction conditions, the -OH group is added to the MOST SUBSTITUTED carbonand the hydrogen is added to the LEAST SUBSTITUTED carbon when there is a choice. This is called Markovnikov's rule.
CH3CH=CH2 + H2O + CH3CHOHCH3
To add the -OH to the least substituted carbon, anti-Markovnikov, the hydroboration-oxidation method is used.
CH3CH=CH2 CH3CH2CH2OH
Ethers
Ethers have the general formula R-O-R’. The common nomenclature for ethers consists of alphabetically naming the hydrocarbon groups making up the etherusing the -yl ending followed by the word ether.
The IUPAC nomenclature for ethers consists of the root of the shorter hydrocarbon then -oxy- followed by the name of the longest hydrocarbon.
Problem 11: Name the following ethers using the common nomenclature and IUPAC nomenclature.
CH3OCH2CH3 CH3CH2OCH2CH2CH3 CH3CH2CHBrOCH2CH2CH3
Ethers as a class tend to be relatively unreactive. Ethers are prepared by the reaction of sodium with an alcohol to form an alkoxide ion, which is thenreacted with another alcohol to produce the ether.
2CH3OH + 2Na à 2CH3O-Na+ + H2
CH3O- + CH3CH2OH à CH3OCH2CH3
Aldehydes
Aldehydes have the general form RCHO with a carbonyl group (-C=O) at the end of the chain. The nomenclature for aldehydes names the root first followed by-al.
Problem 12: Name the following molecules.
CH3 CH2CHO CH3 CHO CH3 CH2CH2 CHO
Aldehydes are made by gentle oxidation of 1° alcohols.
CH3 CH2OH CH3CHO
Ketones
Ketones have a carbonyl group not at the end of a chain. Ketones are made by oxidation of 2° alcohols.

The nomenclature for ketones is similar to that of the alcohols but an -one ending is given the ketone.
Problem 13: Name the following molecules.

Carboxylic Acids
Carboxylic acids are organic acids having the general formula RCOOH, and has the structure . Carboxylic acids are formed by the vigorous oxidation ofalcohols.
CH3CH2CH2CH2OH CH3CH2CH2COOH
The nomenclature for the carboxylic acids is the same as the aldehydes except for the root is followed by -oic acid.
Problem 14: Name the following molecules.
CH3CH2CH2CH2CH2COOH CH3COOH CH3CH2CH2COOH
Esters
Esters are the condensation product of the reaction of alcohols and acids, and have the structure .
CH3CH2CH2COOH + CH3CH2OH CH3CH2CH2COOCH2CH3
Esters are generally sweet smelling molecules with distinct odors. The nomenclature for the esters names the alcohol first followed by the name of the ionof the acid.
Problem 15: Name the following molecules.
CH3COOCH2CH3
CH3CH2COOCH2CH3
CH3CH2COOCH2CH2CH2CH3
Oxidation Reduction Reactions
Alcohols are oxidized to aldehydes and ketones under mild conditions. Under more strenuous conditions (higher temperature and stronger oxidizing agents)they are oxidized to carboxylic acids.
1° CH3CH2CH2OH CH3CH2CHO CH3CH2COOH
2° CH3CHOHCH3 CH3COCH3 NR
3° (CH3)3COH NR
Saponification

Saponification is the making of soap from the treatment of fats and oils with strong base. Glycerol stearate hydrolyzes in base to give glycerol and sodiumstearate. The long chain stearate ion has a hydrophyllic end and a lipophyllic end. The lipophyllic end dissolves into oils and grease leaving thehydrophyllic end exposed to the water forming a micelle which can be emulsified into the water.
Organic Compounds Containing Nitrogen
Amines are classified the same way that alcohols are.
1° 2° 3°

N-butyl amine Ethylmethy amine trimethyl amine
Amines are similar to ammonia since they have a free pair of electrons and can readily react with hydronium ion to form ions.
CH3CH2CH2CH2NH2 + H+ à CH3CH2CH2CH2NH3+ butyl ammonium ion
Polymers
Polymer means many unit. Polymers are formed by several methods.
Addition polymerization occurs when a free radical usually from a peroxide reacts with a double bond to set up a chain reaction.
RO. + RCH=CHR’ à ROCHR-CHR’.
ROCHR-CHR’. + nRCH=CHR’ à RO-(RCH-CHR’)n+1-
Condensation polymerization occurs when a dicarboxylic acids reacts with either a dialcohol or a diamine giving a polyester or polyamiderespectively.
nHOCH2CH2OH + nHOOCCH2CH2CH2COOH à
-(OCH2CH2OOCCH2CH2CH2CO)-n + 2nH2O
nHOOCCH2CH2COOH + nNH2CH2CH2NH2 à
-(OCCH2CH2CONHCH2CH2NH)-n + 2nH2O
Problem 16: Show the reaction for the formation of the polyamide nylon-66.
Biological Macromolecules
Sugar Monomers

Glucose a-pyranose form b-pyranose form a-furanose form
Sugar Polymers


Amino acid Monomer

Alanine Arginine Asparagine Aspartic acid Cystine
Amino acid Polymers (protein)

A.K.A.
ala-arg-asn-asp-cys
Nucloetide Monomer

Answer 2

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