Following are \({ }^{1} \mathrm{H}-\mathrm{NMR}\) and \({ }^{13} \mathrm{C}-\mathrm{NMR}\) spectral data for compound \(\mathrm{F}\left(\mathrm{C}_{12} \mathrm{H}_{16} \mathrm{O}\right)\). From this information, deduce the structure of compound \(F\). $$ \begin{array}{lll} \hline{ }^{1} \text { H-NMR } & \multicolumn{2}{c}{{ }^{13} \text { C-NMR }} \\\ \hline 0.83(\mathrm{~d}, 6 \mathrm{H}) & 207.82 & 50.88 \\ 2.11(\mathrm{~m}, 1 \mathrm{H}) & 134.24 & 50.57 \\ 2.30(\mathrm{~d}, 2 \mathrm{H}) & 129.36 & 24.43 \\ 3.64(\mathrm{~s}, 2 \mathrm{H}) & 128.60 & 22.48 \\ 7.2-7.4(\mathrm{~m}, 5 \mathrm{H}) & 126.86 & \\ \hline \end{array} $$

Short Answer

Expert verified
Answer: The proposed structure of compound F is [C6H5-C-(O-CH2)-(CH(CH3)2)].

Step by step solution

01

Analyzing the 1H-NMR data

First, we will analyze the 1H-NMR chemical shifts and their splitting: 0.83 (d, 6H): A doublet with a chemical shift of 0.83 ppm indicates a group of protons which are likely attached to a carbon next to CH3. In this case, there are 6 protons, meaning we have two methyl groups sharing a chemical environment. These protons are most likely on two equivalent secondary or tertiary carbons. 2.11 (m, 1H): A multiplet at 2.11 ppm indicates a proton that is likely near a carbon with sp3 hybridization, possibly adjacent to a double bond or an electronegative atom. 2.30 (d, 2H): A doublet at 2.30 ppm represents two equivalent protons that might be on the carbon attached to the oxygen atom (which is probably an ether group). 3.64 (s, 2H): A singlet at 3.64 ppm represents two equivalent protons that are likely part of an O-CH2 group. 7.2-7.4 (m, 5H): The multiplet between 7.2-7.4 ppm corresponds to five protons which are likely to be attached to aromatic carbons.
02

Analyzing the 13C-NMR data

We will now analyze the 13C-NMR chemical shifts: 207.82 ppm: A carbon with a chemical shift of 207.82 ppm is likely a carbonyl (C=O) group. The five chemical shifts between approximately 126-134 ppm correspond to the aromatic carbons. 50.88 ppm and 50.57 ppm: These two chemical shifts are likely due to the carbons attached to sp3 hybridized carbons. 24.43 ppm and 22.48 ppm: These chemical shifts likely represent carbons bonded to the oxygen atom or neighboring the oxygen atom.
03

Proposing the structure of compound F

Now we will combine the information from the 1H-NMR and 13C-NMR to propose the structure of compound F (C12H16O). From the 1H-NMR, we know that there are likely five aromatic protons and an O-CH2 group. We also have a carbonyl group due to the chemical shift at 207.82 ppm in the 13C-NMR. From the 1H-NMR data at 0.83 ppm (d, 6H), we know that there are two methyl groups attached to secondary or tertiary carbons. On 13C-NMR, we can match these protons with the carbons' chemical shifts at 24.43 ppm and 22.48 ppm. Thus, the proposed structure of compound F is: [C6H5-C-(O-CH2)-(CH(CH3)2)].

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Following is an equation for iodination of toluene. This reaction does not take place. All that happens under experimental conditions for the formation of radicals is initiation to form iodine radicals, I', followed by termination to reform \(\mathrm{I}_{2}\). How do you account for these observations?

Arrange these compounds in order of increasing acidity: 2,4-dichlorophenol, phenol, cyclohexanol.

A finding that opened a route to \(\beta\)-blockers was the discovery that \(\beta\)-blocking activity is retained if an oxygen atom is interposed between the aromatic ring and the side chain. To see this difference, compare the structures of labetalol (Problem 22.55) and propranolol. Thus, alkylation of phenoxide ions can be used as a way to introduce this side chain. The first of this new class of drugs was propranolol. (a) Show how propanolol can be synthesized from 1-naphthol, epichlorohydrin (Section 11.10), and isopropylamine. (b) Is propranolol chiral? If so, which of the possible stereoisomers are formed in this synthesis?

Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group, and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to \(E\). (d) Propose a mechanism for the conversion of \(F\) to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?

Following is a synthesis for albuterol (Proventil), currently one of the most widely used inhalation bronchodilators. (a) Propose a mechanism for conversion of 4-hydroxybenzaldehyde to \(\mathrm{A}\). (b) Propose reagents and experimental conditions for conversion of \(\mathrm{A}\) to \(\mathrm{B}\). (c) Propose a mechanism for the conversion of B to \(\mathrm{C}\). Hint: Think of trimethylsulfonium iodide as producing a sulfur equivalent of a Wittig reagent. (d) Propose reagents and experimental conditions for the conversion of \(C\) to \(D\). (e) Propose reagents and experimental conditions for the conversion of D to albuterol. (f) Is albuterol chiral? If so, which of the possible stereoisomers are formed in this synthesis?

See all solutions

Recommended explanations on Chemistry Textbooks

View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free