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Chapter 17: Q51P (page 567)

The following 1HNMR spectrum is that of an alcohol, C8H10O

. Propose a structure.

Short Answer

Expert verified

The alcohol with the formula C8H10Othat satisfies the 1H NMR data is 4-methylbenzylalcohol.

Step by step solution

01

1H NMR spectrum

Alcohols exhibit characteristic absorption in the 1H NMR spectrum. Hydrogens on the oxygen bearing carbon atom are deshielded by the electron withdrawing effect of oxygen situated near to it.

02

Structure of the alcohol with the formula C8H10O

The symmetric doublets at 7.10未 and 7.17未 with a relative area of 3.00 indicate that the compound is a para substituted benzene derivative. The signal at 2.32未 with a relative area of 3.00 indicates that the methyl group is a para substituent. The absorption at 4.50未with a relative area of 2.00 indicates a carbon with two hydrogens connected to a hetero atom.

The absorption at 2.43未has a relative area of 1.00 is due to the alcoholic proton. Hence, the compound is p-methylbenzyl alcohol. The structure with the absorption values can be given as:

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Most popular questions from this chapter

Phenols generally have lower pKa鈥檚 than aliphatic alcohols because of resonance stabilization with the aromatic ring. Draw all of the resonance contributors for the phenolate ions below. Make note of how the substituents either stabilize or destabilize the system.

Question: Give IUPAC names for the following compounds:

Rank the following substances in order of increasing acidity:

  1. (CH3)2CHOH, HC鈮�CH, (CF3)2CHOH, CH3OH
  2. Phenol, p-methyl phenol, p-(trifluoromethyl)phenol
  3. Benzyl alcohol, phenol, p-hydroxybenzoic acid

The trimethylsilyl (TMS) protecting group is one of several silicon protecting groups for alcohols. For each reaction, draw the mechanism for the protection of (R)-3-bromo-1-butanol with the following silyl chlorides, using triethylamine as the base:

(a) tert-butyldimethylsilyl chloride (TBS-Cl)

(b) triisopropylsilyl chloride (TIPS-Cl)

(c) triethylsilyl chloride (TES-Cl)

Question: What carbonyl compounds give the following alcohols on reduction with ? Show all possibilities.

(a)

(b)

(c)

(d)CH32CHCH2OH
See all solutions

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