kakashi
2022-02-06
star233
Skilled2023-04-22Added 403 answers
Let's begin by summarizing the given information:
- Compound A is derived from isobutanol, has the molecular formula C4H8O2, and reacts with PCl5 and NH3 to give compounds B and C, respectively.
- Compound B reacts with compound D in the presence of AlCl3 to give compound E with molecular formula C10H12O.
- Compound C is reduced to compound F with molecular formula C4H11N.
- Compound F reacts with E in the presence of catalytic amounts of acid to give an aromatic compound G with molecular formula C14H21N.
To determine the structures of these compounds, let's analyze each reaction separately:
Reaction 1: A + PCl5 → B
This is a substitution reaction where PCl5 replaces the -OH group of A with a chlorine atom, forming compound B. The reaction can be represented as:
CH3 CH3
| |
A: CH3 - C - C - OH + PCl5 → CH3 - C - C - Cl (B)
|
CH3
Compound B has the same number of carbons as A (four) and is likely a halogenated alcohol.
Reaction 2: A + NH3 → C
This is a nucleophilic addition reaction where NH3 adds to the carbonyl group of A, forming an imine intermediate which undergoes hydrolysis to give compound C. The reaction can be represented as:
CH3 CH3
| |
A: CH3 - C - C - OH + NH3 → CH3 - C - C = NH2 (imine)
|
CH3
OH
//
C: CH3 - C - C = NH2 + H2O → CH3 - C - C - NH2 (C)
| |
CH3 CH3
Compound C has the same number of carbons as A (four) and is likely an amide.
Reaction 3: B + D → E
This is a Friedel-Crafts alkylation reaction where compound B is alkylated by compound D in the presence of AlCl3, forming compound E. The reaction can be represented as:
CH3 CH3 CH3 CH3
| | | |
B: CH3 - C - C - Cl + D → CH3 - C - C - CH2 - D+ (intermediate)
| |
CH3 Cl
|
E: CH3 - C - C - CH2 - D+ + Cl- → CH3 - C - C - CH2 - D (E)
| |
CH3 CH3
Compound E has twice the number of carbons as B and is likely a substituted biphenyl.
Reaction 4: C → F
This is a reduction reaction where the carbonyl group of compound C is reduced to a primary amine group, forming compound F. The reaction can be represented as:
CH3 CH3
| |
C: CH3 - C - C - NH2 + 2H2 → CH3 - C - C - NH3+ (F)
| |
CH3 CH3
Compound F has the same number of carbons as C (four) and is likely a primary amine.
Reaction 5: F + E → G
This is a condensation reaction where compound F reacts with compound E in the presence of catalytic amounts of acid to form compound G. The reaction can be represented as:
CH3 CH3 CH3 CH3
| | | |
F: CH3 - C - C - NH3+ + E → CH3 - C - C - CH2 - E
| ||
CH3 Cl
|
G: CH3 CH3 CH3 CH3
| | | |
CH3 - C - C - NH - CH2 - C - C - CH - E
| | | |
CH3 CH3 CH3 CH3
Compound G has twice the number of carbons as F and is likely an aromatic compound.
In summary, the structures of the compounds are as follows:
- Compound A: CH3CH2C(O)CH3 (a methyl ketone derived from isobutanol)
- Compound B: CH3CH2C(Cl)(CH3)OH (a chlorinated alcohol)
- Compound C: CH3CH2C(O)NH2 (a primary amide)
- Compound D: CH3CH2CH2CH2Br (a alkyl halide)
- Compound E: (CH3CH2)2C6H3 (a substituted biphenyl)
- Compound F: CH3CH2CH2NH2 (a primary amine)
- Compound G: (CH3CH2)4C4H2NH (a tetrasubstituted benzene)
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