Chapter 10: PROBLEM 10.41 (page 421)

Question: (a) Draw the structure of (1E,4R)-1,4-dimethylcyclodecene. (b) Draw the enantiomer and name it, including its E,Z and R,S prefixes. (c) Draw two diastereomers and name them, including the E,Z and R,S prefixes.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

E and Z configuration

When there are substituents around the double bond, E or Z configuration is assigned on the following basis:

  • Z: High-priority substituents are on the same side of the C=C bond
  • E: High-priority substituents are on different sides of the C=C bond
02

Structures for a, b, and c

(a) The given compound is (1E,4R)-1,4-dimethylcyclodecene. Its structure is shown below:

(1E,4R)-1,4-dimethylcyclodecene

(b) Compounds with the same formula that are non-superimposable mirror images are termed enantiomers.

The enantiomers of the given compound are shown below:

(1E,4S)-1,4-dimethylcyclodec-1-ene

(c) Compounds having the same formula, that are neither superimposable nor mirror images are termed diastereomers.

The diastereomers of the given compound are shown below:

Diastereomers

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

Question: Draw all stereoisomers formed when 1,2-dimethylcyclohexene is treated with HCl. Label pairs of enantiomers.

Question: Linolenic acid (Table 10.2) and stearidonic acid are omega-3 fatty acids, unsaturated fatty acids that contain the first double bond located at C3, when numbering begins at the methyl end of the chain. Predict how the melting point of stearidonic acid compares with the melting points of linolenic and stearic acids. A current avenue of research is examining the use of soybean oil enriched in stearidonic acid as a healthier alternative to vegetable oils that contain fewer degrees of unsaturation.

Question: Give the structure corresponding to each name.

a. (E)-4-ethylhept-3-ene

b. 3,3-dimethylcyclopentene

c. 4-vinylcyclopentene

d. (Z)-3-isopropylhept-2-ene

e. cis-3,4-dimethylcyclopentene

f. 1-isopropyl-4-propylcyclohexene

g. 3,4-dimethylcyclohex-2-enol

h. 3,5-diethylhex-5-en-3-ol

Question: Draw the products of each reaction, including stereoisomers.

a.

b.

c.

d.

e.

f.

Question: Like other electrophiles, carbocations add to alkenes to form new carbocations, which can then undergo substitution or elimination reactions depending on the reaction conditions. With this in mind, consider the following reactions of nerol, a natural product isolated from lemon grass and other plant sources. Treatment of nerol with TsOH forms α-terpineol as the major product, whereas treatment of nerol with chlorosulfonic acid, HSO3Cl , forms a constitutional isomer, α-cyclogeraniol. Write stepwise mechanisms for both processes. Each mechanism involves the addition of an electrophile—a carbocation— to a double bond.

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