1
Question
(a) How do primary, secondary and teritary amines react with nitrous acid?
(b) Elucidate the structure of glucose.
(b) Elucidate the structure of glucose.
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Solution
(a) The reaction of primary, secondary and tertiary amines with nitrous acid.
Aliphatic primary amines (except methylamine) react with nitrous acid in cold condition to form unstable aliphatic diazonium salt. This salt decomposes to alcohol and nitrogen gas.
CH3−CH2−NH2+HNO2NaNO2/HCl−−−−−−−−→273−278KCH3−CH2−OH+H2O+N2↑
Aromatic primary amines gives relatively stable diazonium salts.
C6H5−NH2+NaNO2HCl273−278K−−−−−−→C6H5−N+2Cl−+NaCl+2H2O
Secondary amines react with nitrous acid to form yellow oily N-nitroso amines.
(CH3−CH2−)2−NH+HNO2NaNO2/HCl−−−−−−−−→273−278K(CH3−CH2−)2−N−N=O+H2O
Aliphatic tertiary amines react with nitrous acid to form water soluble nitrite salts.
(CH3−CH2−)3−N+HNO2NaNO2/HCl−−−−−−−−→273−278K[(CH3−CH2−)3−NH]+NO−2
Aromatic tertiary amines react with nitrous acid and undergo electrophilic ring substitution. A nitroso group is attached to a ring C atom.
(CH3−CH2−)2−N−C6H5+HNO2NaNO2/HCl−−−−−−−−→273−278K(CH3−CH2−)2−N−p−C6H4−N=O+H2O
(b) The structure of glucose:
The molecular formula of glucose is C6H12O6. All six C atoms are linked in a straight chain.
One aldehyde group and 5 hydroxyl groups are present. One hydroxyl group is primary and four hydroxyl groups are secondary.
Glucose has an open chain structure and cyclic structure.
Aliphatic primary amines (except methylamine) react with nitrous acid in cold condition to form unstable aliphatic diazonium salt. This salt decomposes to alcohol and nitrogen gas.
CH3−CH2−NH2+HNO2NaNO2/HCl−−−−−−−−→273−278KCH3−CH2−OH+H2O+N2↑
Aromatic primary amines gives relatively stable diazonium salts.
C6H5−NH2+NaNO2HCl273−278K−−−−−−→C6H5−N+2Cl−+NaCl+2H2O
Secondary amines react with nitrous acid to form yellow oily N-nitroso amines.
(CH3−CH2−)2−NH+HNO2NaNO2/HCl−−−−−−−−→273−278K(CH3−CH2−)2−N−N=O+H2O
Aliphatic tertiary amines react with nitrous acid to form water soluble nitrite salts.
(CH3−CH2−)3−N+HNO2NaNO2/HCl−−−−−−−−→273−278K[(CH3−CH2−)3−NH]+NO−2
Aromatic tertiary amines react with nitrous acid and undergo electrophilic ring substitution. A nitroso group is attached to a ring C atom.
(CH3−CH2−)2−N−C6H5+HNO2NaNO2/HCl−−−−−−−−→273−278K(CH3−CH2−)2−N−p−C6H4−N=O+H2O
(b) The structure of glucose:
The molecular formula of glucose is C6H12O6. All six C atoms are linked in a straight chain.
One aldehyde group and 5 hydroxyl groups are present. One hydroxyl group is primary and four hydroxyl groups are secondary.
Glucose has an open chain structure and cyclic structure.
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