Question 12.1: To which family of organic compounds do the following compou...

To which family of organic compounds do the following compounds belong? Explain.
(a) \begin{array}{r c}\underset{|}{H}\ \quad \underset{|}{H}\quad \; \underset{|}{H}\quad \underset{|}{H}\quad \quad \\ H-C-C=C-C-H \\\quad \quad\quad \quad\overset{|}{H}\quad\quad \quad\quad\quad\;\overset{|}{H} \quad \quad \end{array}      (b)  \begin{array}{r c}\underset{|}{H}\ \quad \underset{|}{H}\quad\underset{|}{H}\quad \underset{|}{H}\quad \quad \\ H-C-C-C-C-H \\\quad \quad\quad \quad\overset{|}{H}\quad \; \overset{|}{H} \quad \overset{|}{O} \quad \; \overset{|}{H} \qquad \\ \overset{|}{H} \qquad \qquad \end{array}

(c)      (d) \begin{array}{r c}\underset{|}{H}\ \quad \underset{|}{H}\qquad \quad \underset{|}{H}\quad \underset{|}{H}\quad \quad \\ H-C-C-C-C-C-H \\\quad \quad\quad \quad\overset{|}{H}\quad \overset{|}{H}\quad \; \overset{||}{O}\quad \; \overset{|}{H} \quad \overset{|}{H} \quad \quad \end{array}

ANALYSIS Identify each functional group from the list in Table 12.1, and name the corresponding family to which the compound belongs.

 

FAMILY NAME FUNCTIONAL GROUP STRUCTURE* SIMPLE EXAMPLE NAME ENDING
Alkane Contains only C—H and C—C single bonds CH_3CH_3   Ethane -ane
Alkene   Ethylene -ene
Alkyne   Acetylene (Ethyne) -yne
Aromatic   Benzene None
Alkyl halide   (X=F, Cl, Br, I) CH_3 – Cl  Methyl chloride None
Alcohol CH_3 – OH  Methyl alcohol (Methanol) -ol
Ether CH_3 – O – CH_3    Dimethyl ether None
Amine CH_3 – NH_2    Methylamine -amine
Aldehyde \begin{array}{r c}\underset{||}{O} \qquad \> \\ CH_3-C-H \end{array}   Acetaldehyde (Ethanal) -al
Ketone \begin{array}{r c}\underset{||}{O} \qquad \quad \> \\ CH_3-C-CH_3 \end{array}  Acetone -one
Carboxylic acid \begin{array}{r c}\underset{||}{O} \qquad \enspace \> \\ CH_3-C-OH \end{array}  Acetic acid -ic acid
Anhydride \begin{array}{r c}\underset{||}{O} \qquad \quad \> \underset{||}{O} \qquad \quad \> \\ CH_3-C-O-C-CH_3 \end{array}  Acetic anhydride None
Ester \begin{array}{r c} \underset{||}{O} \qquad \qquad \quad \> \\ CH_3-C-O-CH_3 \end{array}  Methyl acetate -ate
Amide \begin{array}{r c} \underset{||}{O} \qquad \quad \; \\ CH_3-C-NH_2 \end{array}  Acetamide -amide
*The bonds whose connections are not specified are assumed to be attached to carbon or hydrogen atoms in the rest of the molecule.
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(a) This compound contains only carbon and hydrogen atoms, so it is a hydrocarbon. There is a carbon-carbon double bond, so it is an alkene.
(b) The O — H group bonded to tetravalent carbon identifies this compound as an alcohol.
(c) This compound also contains only carbon and hydrogen atoms, which identifies it as a hydrocarbon. The six-membered carbon ring with alternating double bonds also identifies this compound as an aromatic hydrocarbon compound.
(d) The carbon-oxygen double bond in the middle of the carbon chain (as opposed to at either end of the chain) identifies this compound as a ketone.

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