Question

Which of the following have a meso form? (Recall that the -ol suffix refers to an alcohol, ROH.? (a) 2,3-Butanediol (b) 2,3-Pentanediol (c) 2,4-Pentanediol

   Which of the following have a meso form? (Recall that the -ol suffix refers to an alcohol, ROH.?
(a) 2,3-Butanediol
(b) 2,3-Pentanediol
(c) 2,4-Pentanediol

Organic Chemistry

Organic Chemistry

John McMurry 8th Edition

Chapter 5, Problem 17

Instant Answer

Solved by Expert Bobby Barnes

05/15/2020

Step 1

(a) 2,3-Butanediol: Butane means four carbons. So, we draw a four carbon chain and then put an alcohol group on the second and third carbons. (b) 2,3-Pentanediol: Pentane means five carbons. So, we draw a five carbon chain and then put an alcohol group on the Show more…

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Which of the following have a meso form? (Recall that the -ol suffix refers to an alcohol, ROH.? (a) 2,3-Butanediol (b) 2,3-Pentanediol (c) 2,4-Pentanediol

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Key Concepts

Chirality

Chirality refers to the geometric property of a molecule that is not superimposable on its mirror image, typically due to the presence of one or more stereocenters. Understanding chirality is crucial when discussing optical activity and the differentiation between chiral and meso compounds.

Stereochemistry

Stereochemistry is the branch of chemistry that deals with the spatial arrangements of atoms within molecules. It encompasses the study of stereoisomers, including enantiomers and diastereomers, and is essential for analyzing compounds that may have different properties despite having the same connectivity.

Meso Compounds

Meso compounds are molecules that contain stereocenters yet are overall achiral due to an internal plane of symmetry. This symmetry makes such compounds optically inactive despite having chiral centers, which is a key concept in understanding stereoisomerism.

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Transcript

00:01 We want to determine which of the following molecules will have a meso form.

00:07 So let's go ahead and first draw these out.

00:12 So remember, butane means four carbons.

00:18 And so the way i remember, at least the first four is mike eats peanut butter.

00:24 So the b means it's the fourth one in that.

00:29 So it's going to be four carbon.

00:31 So let's just go ahead and draw four carbon chain.

00:33 And then it tells us that position's two and three.

00:36 We're going to have an alcohol.

00:39 So let's just put an alcohol on each of these positions here.

00:44 All right.

00:44 So we need to see if we can come up with some kind of mirror image.

00:48 Well, one thing we can do is because remember we can rotate these sigma bonds is just flip this up.

00:59 So like we can hold this in place and then rotate it 180 degrees like this.

01:05 And in doing that, we're going to end up with this alcohol here and then this alcohol here.

01:14 And now if we were to have both of these alcohols on the same side, notice that we could just cut going straight down like this.

01:22 And then we would have a plane of symmetry.

01:25 So it looks like a can have a miso form.

01:28 All right, now what about b? so this is pentane.

01:36 So i remember everything after five as like the shape.

01:40 So pentane would be the same thing as a pentagon, so five -sided shape.

01:44 So five carbon chain.

01:46 So one, two, three, four, five...

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